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DOI： 10.1002/cplu.201900087

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Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley-VCH Verlag  

DOI： 10.1002/anie.201800471

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DOI： 10.1002/chem.201703664

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DOI： 10.1002/anie.201510734

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DOI： 10.1002/tcr.201402101

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Authorship：Lead author,　Corresponding author   Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：The Society of Synthetic Organic Chemistry, Japan  

Phosphole has a low aromaticity and exhibits characteristic optical and electrochemical properties derived from the phosphorus-bridged 1,3-diene π system. In addition, phosphole has an active lone pair at phosphorus. The most remarkable feature of the phosphole-based π-systems is that their fundamental properties are tunable by chemical functionalizations at the phosphorus center. In this regard, phosphole-based π-systems are now regarded as one of the future materials for use in optoelectronics. In this article, we would like to briefly summarize our recent results on the synthesis of novel π-conjugated phosphole derivatives with representative examples, which contain phosphole-vinylene, phosphole-acetylene, phosphole-heterole, phosphole-benzene, phosphole-phosphole, benzo[c]phosphole, acenaphtho[c]phoshole, and diacenaphtho[b,d]phosphole skeletons. The target compounds were successfully prepared by two main approaches, titanacycle method and Stille coupling. Selected structural, optical, and electrochemical data for a few derivatives are also presented. The results described herein would give valuable information and guidelines for designing phosphole-based opto-electrochemical materials.

DOI： 10.5059/yukigoseikyokaishi.70.629

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Abstract

In contrast to the great advances of phthalocyanine‐based materials, the potential of 5,10,15‐triazaporphyrins has not been realized because of the lack of fundamental information about their structure‐property relationships. Here, we report new derivatives of dibenzo‐5,10,15‐triazaporphyrin (DBTriAP) with aryl or alkyl substituents at the meso and/or β positions. Freebases of DBTriAP were prepared by the condensation of two types of 1,9‐dibromodipyrrins with 1,3‐diiminoisoindoline and subsequent functionalization of the β‐pyrrolic carbons. Zinc(II) complexes of DBTriAP were obtained by complexation of the corresponding freebases with zinc(II) acetate. The optical and electrochemical properties of the DBTriAP derivatives were studied by steady‐state and transient ultraviolet/visible absorption/emission spectroscopy, magnetic circular dichroism spectroscopy, cyclic voltammetry (CV), and density functional theory (DFT) calculations. Replacing the β‐pyrrolic hydrogens of the 5‐mesityl‐DBTriAP derivatives with aryl groups resulted in substantial red shifts of the low‐energy absorption band because of the effective π‐delocalization and/or charge‐transfer interaction with the DBTriAP chromophore. The 2,3,17,18‐tetraethyl‐DBTriAP freebase exhibited split redox processes in its cyclic voltammogram, suggesting the rapid formation of a π‐stacked dimer radical cation facilitated by the highly planar structure. Most of the DBTriAP derivatives emitted red fluorescence with quantum yields of 0.07–0.31, indicating their potential as luminescent materials.

DOI： 10.1002/chem.202502463

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Oxford University Press (OUP)  

Abstract

Photoexcitation dynamics of a series of 2-aryl-3H-1,3-benzazaphosphole oxides (ABPO) were studied using ultrafast time-resolved fluorescence spectroscopy and transient absorption spectroscopy. The fluorescence quantum yields and lifetimes strongly depended on the substituents on the phenyl ring at the 2-position, and generally fluorescence lifetimes were very short. Compound (1d) that has a 4-(N,N-diphenylamino)phenyl group at the 2-position showed intense fluorescence in nonpolar solvents, although the fluorescence was quite weak in polar solvents. The time-resolved fluorescence spectrum of 1d showed a large dynamic shift, accompanied by a decrease in fluorescence intensity. The transient absorption spectrum of 1d showed complex spectral dynamics. From the singular value decomposition analysis of the time-resolved spectra, the spectral dynamics were assigned to the charge transfer formation accompanying the rotation of the phenyl ring at 2-position predicted by the theoretical calculations (K. Sugiyama et al., J. Phys. Chem. B, 2025, 129, 2701). A compound with an ortho-hydroxyphenyl at the 2-position (1e-OH) showed intramolecular proton transfer in aprotic solvents, showing dual fluorescence from the normal and tautomer bands. In methanol, a new fluorescence band appeared besides the bands from the normal and tautomer states, which was assigned to the hydrogen-bonding complex with the solvent by the theoretical calculations.

DOI： 10.1093/bulcsj/uoaf076

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DOI： 10.1021/acs.orglett.5c02644

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Abstract

With the aim of exploring 5,15‐diazaporphyrinoids with four meso substituents (R₄DAP) as a new class of π‐electron donors, the generation of air‐stable π‐radical ion pairs formed from R₄DAP and 7,7,8,8‐tetracyanoquinodimethane (TCNQ) derivatives has been demonstrated. Nickel(II) and copper(II) complexes of the 20π‐electron antiaromatic R₄DAP (R₄DAPM; M = Ni, Cu) were prepared via a metal‐templated cyclization method and used for the reaction with TCNQ. Single electron transfer from R₄DAPM to TCNQ spontaneously occurred in CH₂Cl₂ at room temperature to afford the corresponding radical ion pair, [R₄DAPM^•+][TCNQ^•−]. Similarly, R₄DAPNi reacted with 2,3,5,6‐tetrafluoro‐TCNQ (F₄TCNQ) to afford [R₄DAPNi^•+][F₄TCNQ^•−]. The absorption spectra of [R₄DAPM^•+][TCNQ^•−] in the visible–near IR region were almost identical to the superposed spectra of the independently prepared cation‐ and anion‐radical references, indicating negligible π─π orbital interaction between the two radical ions in solution. However, the electron paramagnetic resonance spectrum of [R₄DAPNi^•+][F₄TCNQ^•−] in CH₂Cl₂ showed a broad signal attributable to the coupled spin state, suggesting the definite contribution of spin–spin interaction between the two ion‐paired radicals. The results of this study provide valuable information for understanding the fundamental properties of π‐radical ion pairs.

DOI： 10.1002/ajoc.202500312

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The central metals in group 14 metalloporphyrins significantly influence the optical, redox, and magnetic properties of the porphyrin [Formula: see text]-electron systems. This study reports the first examples of Si(IV) complexes of 10,20-diaryl-5,15-diazaporphyrin (Ar₂DAP) and 5,10,20-triaryl-5,15-diazaporphyrin (Ar₃DAP), designed to explore the effects of meso-nitrogen atoms and net charge on these fundamental properties of the porphyrin ring. Reacting the free base of Ar₂DAP with HSiCl₃, followed by metathesis of axial ligands, yielded the corresponding Si(IV) complexes (Ar₂DAPSiX₂; X [Formula: see text] OH, F). Copper-catalyzed [Formula: see text]-phenylation of Ar₂DAPSiF₂ and subsequent redox reactions produced 18[Formula: see text]- and 19[Formula: see text]-electron derivatives of Ar₃DAPSiF₂. Nuclear magnetic resonance spectroscopy, cyclic voltammetry, and density functional theory calculations revealed that the diatropic ring-current effects derived from the aromatic 18[Formula: see text]-electron systems of Ar₂DAPSiX₂ and Ar₃DAPSiF₂ strongly depend on the net charge and dipole moment of the DAP ligand. All Si(IV) complexes exhibited fluorescence, with Stokes shifts of 120–310 cm[Formula: see text]. Measurements of fluorescence quantum yields and lifetimes indicated that [Formula: see text]-phenylation primarily reduced the nonradiative decay rate constant. These findings provided insights into the influence of net charge on the aromatic character, as well as the optical and redox properties, of six-coordinate Si(IV) complexes of DAP derivatives.

DOI： 10.1142/s1088424625500397

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Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.jpcb.4c05872

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DOI： 10.1002/asia.202401370

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Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.organomet.4c00395

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Abstract

Porphyrinoids in the 20π‐electron state have been extensively studied from the fundamental viewpoint of investigating their structure–antiaromaticity relationships. However, most of the 20π porphyrinoids are highly distorted and unstable in air, which hinder the comprehensive analysis of paratropic ring‐current effects derived from planar π‐electron systems. Herein, we present the first examples of antiaromatic Sn(IV) complexes of 5,10,15,20‐tetraaryl‐5,15‐diazaporphyrinoids (SnX₂TADAPs), prepared by the complexation of the corresponding freebases with Sn(II) chloride under aerobic conditions and subsequent metathesis of the axial ligands, that show paratropic ring‐current effects. Notably, both neutral 20π‐electron derivatives and 19π‐electron radical cations of SnX₂TADAP are extremely stable in air owing to the intrinsic electronic effects of the central Sn(IV) unit and meso nitrogen atoms. NMR spectroscopy, cyclic voltammetry, and density functional theory calculations were performed to assess the ring‐current effects and orbital energies of a series of the 20π‐electron SnX₂TADAPs, and the results reveal that the paratropic ring‐current effects arising from the planar 20π‐electron DAP ring increases with a decrease in the HOMO–LUMO energy gap.

DOI： 10.1002/chem.202404092

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ABSTRACT

A monoanionic bidentate [PN]‐type ligand based on dibenzophosphole was synthesized, and its coordination properties toward titanium and zirconium were investigated. The complexes [PN]M (NR₂)₃ (M = Ti, R = Me; M = Zr, R = Et) were synthesized through the reaction of 4‐(1H‐pyrrole‐2‐yl)dibenzophosphole, [PN]H, with three equivalents of Ti (NMe₂)₄ or Zr (NEt₂)₄. Both titanium and zirconium complexes featuring the [PN] ligand were characterized by NMR and elemental analysis. Single‐crystal X‐ray crystallography unveiled the solid‐state structure of [PN]Zr (NEt₂)₃, with the pyrrolido group coordinated to the zirconium center in the η¹‐mode. Ethylene polymerization at 0.4 MPa using these complexes and dried modified methylaluminoxane (dMMAO) as a cocatalyst yielded linear polyethylene (PE) with a melting point of 128°C–136°C; the polymerization activity reached up to 64 kg/mol (Zr)·h·bar at 70°C.

DOI： 10.1002/aoc.7928

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DOI： 10.1002/chem.202400807

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<jats:title>Abstract</jats:title>
<jats:p>We report herein an improved method for the quantitative preparation of free bases of 5,10,15,20-tetraaryl-5,15-diazaporphyrinoid (TADAP) using Me3SiBr–MeOH to treat the corresponding zinc(II) complexes. Metallation of the free base with HSiCl3 followed by Si–X metathesis with SbF3 and redox reactions afforded difluorosilicon(IV) complexes of TADAP.</jats:p>

DOI： 10.1093/bulcsj/uoad022

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DOI： 10.1016/j.molliq.2023.121934

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Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/bcsj.20230071

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：World Scientific Pub Co Pte Ltd  

<jats:p> Singlet–singlet and triplet-triplet energy-transfer processes between anthracenes and porphyrins have received considerable attention in materials chemistry. Herein, we report the first examples of 3,5-bis(10-phenylanthracen-9-yl)benzene-appended porphyrins (BPABPs) designed to study intramolecular energy transfer between two chromophores. The Curtius rearrangement of 3,5-bis(10-phenylanthracen-9-yl)benzoyl azide in the presence of the platinum(II) complex of 5,10,15-tris(3,5-di-tert-butylphenyl)-20-(3-hydroxyphenyl)porphyrin or its free base in toluene afforded the corresponding BPABP. Spectroscopy, cyclic voltammetry, and density functional theory calculations revealed that the anthracene and porphyrin [Formula: see text]-electron systems of the BPABPs are not conjugated and consequently do not affect each other’s absorption properties. In contrast, the BPABPs exhibited considerably different luminescence properties to those of phenyl 3,5-bis(10-phenylanthracen-9-yl)carbamate and 5,10,15-tris(3,5-di-tert-butylphenyl)-20-(3-methoxyphenyl)porphyrins; the anthracene units of the BPABPs show considerably quenched fluorescence compared to that of the reference anthracene, indicative of efficient intramolecular singlet–singlet energy transfer from the anthracene to the porphyrin unit. The phosphorescence quantum yield of the Pt complex of BPABP is comparable to that of the reference Pt-porphyrin, which suggests that intramolecular triplet-triplet energy transfer from the Pt-porphyrin to the anthracene unit is inefficient. The present findings improve our understanding of how structural factors and excited-state energy levels affect energy transfer and triplet-triplet annihilation upconversion processes of covalently linked bisanthracene-appended porphyrins. </jats:p>

DOI： 10.1142/s1088424623500840

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1,2,5,10-Tetraphenylanthra[2,3-b]phosphole oxides and 1-methyl-1,2,5,10-tetraphenylanthra[2,3-b]phospholium salts were prepared, and their optical properties were investigated. The substituent at the para position and the fused anthracene moiety were found to exert significant impacts on the fluorescence properties of the P-bridged 2-styrylanthracene skeleton.

DOI： 10.1021/acs.joc.2c01107

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DOI： 10.1246/bcsj.20220002

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Porphyrins containing hydrophilic auxiliaries have received considerable attention. Herein we report the first examples of strongly hydrophilic copper(II) complexes of 5,10,15,20-tetraaryl-5,15-diazaporphyrins (TADAPs) substituted with carboxy or (2,3-dihydroxypropyl)carbamoyl groups. Metal-templated cyclization reactions of a common dipyrrin precursor with nickel(II) or copper(II) acetate afforded the corresponding metal(II) complexes of 5,10,15,20-tetrakis(4-alkoxycarbonylphenyl)-5,15-diazaporphyrin (M-TADAP-COOR; M = Ni, Cu) as air-stable 19[Formula: see text] radical cations, which were reversibly interconvertible with 20[Formula: see text]- and 18[Formula: see text]-electron states by redox reactions. NMR spectroscopy of 20[Formula: see text] and 18[Formula: see text] Ni-TADAP-COORs revealed antiaromatic and aromatic characteristics, respectively. Alkaline hydrolysis of the 19[Formula: see text] Cu-TADAP-COOR afforded a carboxylic acid, Cu-TADAP-COOH, which was freely soluble in water under basic conditions, but poorly soluble under neutral or acidic conditions. Dehydrative condensation of Cu-TADAP-COOH with 2,3-bis((tert-butyldimethylsilyl)oxy)propan-1-amine followed by deprotection of the silyl groups afforded an amide, Cu-TADAP-CONHR, with four (2,3-dihydroxypropyl)carbamoyl groups. Although the 20[Formula: see text] Cu-TADAP-CONHR was poorly soluble in water, oxidation of its DAP ring notably changed the solubility, and the resulting 18[Formula: see text] dication was homogeneously dispersed in neutral water. Cyclic voltammetry of the present TADAP derivatives showed the 21[Formula: see text]/20[Formula: see text], 20[Formula: see text]/19[Formula: see text] and 19[Formula: see text]/18[Formula: see text] redox couples in the range of −1.8 to +0.2 V vs. Fc/Fc[Formula: see text]. Furthermore, Cu-TADAP-CONHR exhibited reversible redox processes in neutral water. This study shows that TADAP could be a potential platform for the development of hydrophilic DAP-based materials.

DOI： 10.1142/s1088424621500917

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/cl.210218

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DOI： 10.1021/acs.jpcb.1c02360

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DOI： 10.1142/s1088424619500822

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DOI： 10.1002/ajoc.201900085

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DOI： 10.1002/hc.21456

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DOI： 10.1021/acs.joc.8b00087

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/acs.joc.8b00030

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We have established a convenient method for the base-promoted direct amination of β-unsubstituted 5,15-diazaporphyrins (DAPs) with secondary and primary amines to produce 3,7,13,17-tetraamino- and 3-amino-DAPs, respectively, regioselectively. The amino groups attached at the periphery cause significant red shifts of the absorption bands as a result of their perturbation of the HOMO and/or LUMO in the DAP π-system. The palladium complex of a 3,7,13,17-tetrakis(diphenylamino)-DAP generated singlet oxygen in high yield under irradiation with near-infrared light.

DOI： 10.1002/ange.201800471

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

DOI： 10.1021/acs.joc.8b00030

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DOI： 10.1246/bcsj.20180123

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DOI： 10.1142/S1088424618500529

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Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry  

DOI： 10.1039/c8dt01503a

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DOI： 10.1021/jacs.7b09424

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DOI： 10.1039/c7dt01839h

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/ja203822q

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/acs.jpcb.7b03658

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DOI： 10.1002/cplu.201700051

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DOI： 10.1002/asia.201700204

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DOI： 10.1002/ajoc.201600612

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/acs.chemrev.6b00460

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DOI： 10.1002/ejoc.201600611

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DOI： 10.1039/c5dt03362d

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DOI： 10.1021/jp510903a

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/acs.joc.5b00541

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DOI： 10.1142/S1088424615500509

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DOI： 10.1002/chem.201405482

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DOI： 10.1002/hc.21188

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/ejic.201301132

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DOI： 10.1002/chem.201304626

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DOI： 10.1021/jp410436f

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DOI： 10.1021/ol401994e

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Carboxyphenylethynyl-substituted diazaporphyrin has been synthesized to assess the utility of diazaporphyrins in dye-sensitized solar cells for the first time. The diazaporphyrin-sensitized TiO₂ cell exhibited photocurrent generation in the visible region of 400–700 nm together with a power conversion efficiency of 0.08%.

DOI： 10.1246/cl.130212

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DOI： 10.1021/ol4000982

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DOI： 10.1002/chem.201203047

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DOI： 10.1021/ic301835c

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DOI： 10.1002/asia.201200492

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Society of Synthetic Organic Chemistry, Japan  

Phosphole has a low aromaticity and exhibits characteristic optical and electrochemical properties derived from the phosphorus-bridged 1,3-diene π system. In addition, phosphole has an active lone pair at phosphorus. The most remarkable feature of the phosphole-based π-systems is that their fundamental properties are tunable by chemical functionalizations at the phosphorus center. In this regard, phosphole-based π-systems are now regarded as one of the future materials for use in optoelectronics. In this article, we would like to briefly summarize our recent results on the synthesis of novel π-conjugated phosphole derivatives with representative examples, which contain phosphole-vinylene, phosphole-acetylene, phosphole-heterole, phosphole-benzene, phosphole-phosphole, benzo[c]phosphole, acenaphtho[c]phoshole, and diacenaphtho[b,d]phosphole skeletons. The target compounds were successfully prepared by two main approaches, titanacycle method and Stille coupling. Selected structural, optical, and electrochemical data for a few derivatives are also presented. The results described herein would give valuable information and guidelines for designing phosphole-based opto-electrochemical materials.

DOI： 10.5059/yukigoseikyokaishi.70.629

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DOI： 10.1002/chem.201200463

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DOI： 10.1002/chem.201103843

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DOI： 10.1021/ja210205v

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DOI： 10.1021/jp208775x

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DOI： 10.1007/128_2011_167

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DOI： 10.1142/S1088424611004087

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DOI： 10.1246/cl.2011.919

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DOI： 10.1021/jp2030208

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DOI： 10.1021/ja203822q

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DOI： 10.1246/bcsj.20100326

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DOI： 10.1002/cssc.201100029

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DOI： 10.1002/anie.201007065

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ACADEMIC PRESS INC ELSEVIER SCIENCE  

DOI： 10.1016/j.jcis.2011.01.066

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Language：English   Publisher：American Institute of Physics  

DOI： 10.1063/1.3565237

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DOI： 10.1002/hc.20708

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DOI： 10.1002/anie.201102782

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DOI： 10.1039/c0ee00482k

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DOI： 10.1039/c1jm11531f

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DOI： 10.1021/jp911141s

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DOI： 10.1016/j.crci.2010.03.017

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

DOI： 10.1021/jp1004049

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DOI： 10.1021/ol100926q

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DOI： 10.1021/jp102486b

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

DOI： 10.1246/cl.2010.448

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/adma.200903056

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DOI： 10.1021/ol100114j

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DOI： 10.1351/PAC-CON-09-08-05

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

DOI： 10.1021/jp910832a

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DOI： 10.1021/jo902060b

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PubMed

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DOI： 10.1080/10426501003773431

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Chemical Society of Japan  

DOI： 10.1246/cl.2010.448

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

DOI： 10.1039/c0cc00709a

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

DOI： 10.1021/om900745t

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

DOI： 10.1021/jp907288h

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DOI： 10.1021/ja901166a

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DOI： 10.1021/ar900075e

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DOI： 10.1021/ol901194m

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DOI： 10.1021/jp902001z

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DOI： 10.1021/jp902623g

J-GLOBAL

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DOI： 10.1021/ja8096465

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PubMed

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/anie.200900542

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Authorship：Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/chem.200901378

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

DOI： 10.1039/b819255n

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1246/bcsj.81.1621

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

DOI： 10.1021/jp807991k

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

DOI： 10.1039/b803272f

CiNii Article

CiNii Books

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Fused five-membered zinc porphyrin carboxylic acid has been synthesized to improve light-harvesting capability in the visible and near-infrared regions. The fused porphyrin-sensitized TiO<SUB>2</SUB> cell exhibited the photocurrent generation extending over 800 nm, although the power conversion efficiency was found to be moderate (0.30%).

DOI： 10.1246/cl.2008.846

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/cphc.200800270

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DOI： 10.1021/om800099h

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/jo800532n

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/ol8005453

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/jp710400p

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/cssc.200700138

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

DOI： 10.1021/ol7029118

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Authorship：Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/ejoc.200701008

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

DOI： 10.1021/ja076709o

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/ja710542e

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/ja807742g

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/chem.200801017

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/asia.200800229

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DOI： 10.1002/chem.200702053

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Language：English   Publishing type：Research paper (scientific journal)  

5323

DOI： 10.1021/jp805122z

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/chem.200700446

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

DOI： 10.1021/jp0726079

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

DOI： 10.1021/jo070822f

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELSEVIER SCIENCE BV  

DOI： 10.1016/j.cplett.2007.07.013

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/jp072075w

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DOI： 10.1021/jp071604t

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/j.tetlet.2007.02.085

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/jp067290b

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/chem.200600835

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/ol070556s

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/asia.200700191

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

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DOI： 10.1021/jp068893q

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DOI： 10.1021/ol622763

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DOI： 10.1021/la061527d

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DOI： 10.1021/ja0640039

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DOI： 10.1021/ol061506a

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/adma.200600312

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/jo0605748

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DOI： 10.1021/la0533314

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DOI： 10.1021/om060300a

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/jp061524+

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/j.tet.2005.05.109

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/b513707a

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/la0533314

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/chem.200500610

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DOI： 10.1021/jp044725r

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/adma.200401770

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DOI： 10.1021/jp0537409

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/jp044725r

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/chem.200500610

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

DOI： 10.1021/jo0485740

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DOI： 10.1021/om0494115

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

DOI： 10.1021/jo0492721

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/jp037625e

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/b404690k

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Language：English   Publisher：Elsevier  

DOI： 10.1016/S1389-5567(03)00004-2

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/ic0110575

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1055/s-2002-23536

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/1521-3773(20020816)41:16<3028::AID-ANIE3028>3.0.CO;2-U

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/ic0110575

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/ja003623l

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PubMed

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Language：Japanese   Publisher：The Society of Synthetic Organic Chemistry, Japan  

The syntheses and reactions of bismuthonium salts and bismuth ylides are reported. Various types of bismuthonium salts bearing a Bi-C<I><SUB>sp</SUB></I><I><SUP>3</SUP></I>, Bi-C<I><SUB>sp</SUB></I><I><SUP>2</SUP></I>, or Bi-C<I><SUB>sp</SUB></I> bond have been prepared by the Lewis-acid promoted reaction of triphenylbismuth difluoride with organometallic reagents. The bismuthonium salts thus obtained behave as alkyl cation equivalents, alkenyl cation equivalents, and carbene precursors. The bismuth ylides bearing a carbonyl group at the ylidic carbon react with carbonyl compounds to undergo epoxidation, transposition, or ring expansion depending on the structure of the substrates employed. These reaction modes are characteristic of bismuth among the group 15 elements. The stabilized bismuth ylides bearing a highly cross-conjugated ylidic carbon decompose, at an elevated temperature or in the presence of a copper catalyst, to give trisubstituted oxazoles. The observed unique reactivities of the bismuthonium salts and the bismuth ylides are ascribed to the good leaving ability of the triarylbismuthonio group.

DOI： 10.5059/yukigoseikyokaishi.59.834

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Other Link： https://jlc.jst.go.jp/DN/JALC/00122798045?from=CiNii

Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1055/s-2001-14565

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/ja010584k

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/S0022-328X(00)00295-3

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/om000133t

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DOI： 10.1021/om000095d

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/ic991120e

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/S0022-328X(99)00506-9

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/A900751B

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1055/s-1999-3407

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/ic981334g

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/jo990690t

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/om990252c

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/om980914i

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/A803946A

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry  

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Authorship：Lead author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/om980184e

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/om9804531

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Chemical Society of Japan  

DOI： 10.1246/cl.1998.127

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry  

DOI： 10.1039/a801879k

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/om980411c

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/om9701377

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry  

DOI： 10.1039/a706338e

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/om960320k

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/P19960001971

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/om9509709

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry  

DOI： 10.1039/cc9960002697

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Chemical Society of Japan  

DOI： 10.1246/bcsj.69.2673

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/0040-4039(95)01600-7

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/P19950002543

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

DOI： 10.1021/jo00119a056

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/P19940002703

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/0040-4039(94)88281-9

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Authorship：Lead author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/P19940001739

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/P19930002969

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1055/s-1993-26027

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Authorship：Lead author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/S0040-4039(00)61358-8

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/P19930002411

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/S0040-4039(00)77490-9

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Authorship：Lead author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Chemical Society of Japan  

Bismuth trichloride reacts smoothly with mesityl- and 2,4,6-triisopropylphenylmagnesium bromides in boiling tetrahydrofuran to form the corresponding triarylbismuthines in good yields, while a similar reaction with 2,4,6-triisopropylphenylmagnesium bromide halts at diarylation stage, giving chlorobis(2,4,6-triisopropylphenyl)bismuthine as the sole product. Several crowded alkyl-, alkenyl-, and alkyn-yldiarylbismuthines have been prepared from the above diarychlorobismuthine through the reaction with an appropriate organolithium reagent.

DOI： 10.1246/bcsj.65.3504

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Chemical Society of Japan  

DOI： 10.1246/cl.1991.105

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/poc.610040806

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Chemical Society of Japan  

DOI： 10.1246/bcsj.63.2218

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Chemical Society of Japan  

Thermal reactions of acylquinones with allylstannanes in benzene afforded several kinds of product after column chromatography on silica gel; acyl allyl quinones, acyl allyl epoxy quinones, cyclopentanoid compounds including stannyl moiety, allyl hydroxy quinones, acyl hydroquinones, and acyl allyl hydroquinones. The main product comprises cyclopentanoid compounds, which are novel [2+3] cyclo adducts with 1,2-migration of trialkylstannyl moiety. Spectroscopic examinations (<SUP>1</SUP>H NMR and Vis-UV) enabled us to confirm the reaction pathways that four types of precursors were initially generated via polarized tight pair and inverted to isolated products during purification by column chromatography. Similar reactions in acetonitrile showed a remarkable difference in the reactivity, that is, acyl allyl quinones and the corresponding hydroquinones are obtained, but the [2+3] cyclo adducts are not produced at all. From <SUP>1</SUP>H NMR examination, it was confirmed that three types of precursor are generated via solvent separated ion pairs at the initial stage. The rather strong reactivity of acylquinones towards allylstannanes will be due to electron withdrawing ability of acyl group.

DOI： 10.1246/bcsj.62.3877

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1246/nikkashi.1989.1351

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Total pages：636   Responsible for pages：21–245   Language：English Book type：Scholarly book

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Total pages：636   Responsible for pages：247–327   Language：English Book type：Scholarly book

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Total pages：777   Responsible for pages：223–241   Language：English Book type：Scholarly book

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Total pages：245   Responsible for pages：123–127   Language：Japanese Book type：Scholarly book

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Total pages：238   Responsible for pages：102–114   Language：Japanese Book type：Scholarly book

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Total pages：409   Responsible for pages：114–131   Language：Japanese Book type：Scholarly book

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Total pages：462   Responsible for pages：173–176   Language：Japanese Book type：Scholarly book

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Total pages：462   Responsible for pages：113–120   Language：Japanese Book type：Scholarly book

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Total pages：272   Responsible for pages：246–250   Language：Japanese Book type：Scholarly book

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Total pages：272   Responsible for pages：149–165   Language：Japanese Book type：Scholarly book

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Language：Japanese   Publisher：The Society of Physical Organic Chemistry, Japan  

Core-modified porphyrins are one of the porphyrin analogues, in which at least one core nitrogen atom is replaced by another atom. Although the chemistry of core-modified porphyrins has attracted much attention, phosphorous-containing porphyrins, namely &quot;phosphaporphyrins&quot;, have not been prepared. Here we report the first synthesis of phosphaporphyrin and its aromaticity as well as optical and electrochemical properties. A phosphaporphyrin was synthesized via acid-promoted condensation of phosphatripyrrane with 2,5-bis[hydroxy(phenyl)methyl]thiophene. The NMR and UV-vis absorption spectra, and CV has revealed that the phosphaporphyrin possesses a considerable aromaticity and a relatively narrow HOMO-LUMO energy gap.

DOI： 10.11494/kisoyuki.18.0.17.0

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Language：Japanese   Publisher：技術情報協会  

CiNii Article

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Event date： 2009

Language：Japanese  

It is known that phosphole has a high electron-accepting ability. To construct chemically and thermally stable pi-conjugated phospholes, we designed three types of naphthalene-fused phosphole derivatives, and succeeded in preparing the desired compounds based on a titanacycle methodology. The structure-property relationship will be presented.

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Event date： 2008.10

Language：Japanese  

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Event date： 2008.10

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Event date： 2008.9

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Event date： 2008.9

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Event date： 2008.9

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Event date： 2008.9

Language：Japanese  

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Event date： 2008.9

Language：Japanese  

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Event date： 2008.9

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Event date： 2008.9

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Event date： 2008.5

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Event date： 2008.3

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Event date： 2008.3

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Event date： 2008.3

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Event date： 2008.3

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Event date： 2008.3

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Event date： 2008.3

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Event date： 2008.3

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Event date： 2008.3

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Event date： 2008.3

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Event date： 2008.3

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Event date： 2008.3

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Event date： 2008

Language：Japanese  

Three types of bithiophene-fused benzo[&lt;I&gt;c&lt;/I&gt;]phospholes were synthesized via TiII-mediated intramolecular cyclization of dialkynylated bithiophene derivatives. The X-ray structures, theoretical calculations, UV-vis absorption and fluorescence spectra, and electrochemical measurements have revealed that the structural, optical, and electrochemical properties of the bithiophene-fused benzo[&lt;I&gt;c&lt;/I&gt;]phospholes vary considerably depending on the pi-conjugation modes at the bithiophene subunits. The appropriately ring-annulated sigma3-P derivatives were found to emit fluorescence in the orange-to-red region, and the P-oxo derivatives proved to undergo reversible one-electron reduction in cyclic voltammetry

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Event date： 2007.12

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Event date： 2007.9

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Event date： 2007.9

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Event date： 2007.9

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Event date： 2007.9

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Event date： 2007.9

Language：Japanese  

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Event date： 2007.9

Language：Japanese  

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Event date： 2007.9

Language：Japanese  

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Event date： 2007.9

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Event date： 2007.8

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Event date： 2007.8

Language：Japanese  

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