研究者詳細 - 福井　識人

論文 - 福井　識人

分割表示 68 件中 41 - 60 件目／全件表示 >>

Easily Switchable 18π‐, 19π‐, and 20π‐Conjugation of Diazaporphyrin Double‐Pincer Bispalladium Complexes 査読有り

Takahiro Sakurai, Yuya Hiraoka, Hisaaki Tanaka, Yoshihiro Miyake, Norihito Fukui, Hiroshi Shinokubo

Angewandte Chemie International Edition 62 巻 ( 12 ) 2023年2月

One-dimensional stacking array of 10,20-diphenyl-5,15-diazaporphyrin metal complexes 査読有り

Shiho Mori, Takahiro Sakurai, Tsubasa Nishimura, Norihito Fukui, Yoshihiro Miyake, Hiroshi Shinokubo

Journal of Porphyrins and Phthalocyanines 頁： A - G 2023年1月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：World Scientific Pub Co Pte Ltd

We prepared a free-base 10,20-diphenyl-5,15-diazaporphyrin and its Ni(II), Cu(II), Pd(II), and Pt(II) complexes. These molecules uniformly form an infinite one-dimensional [Formula: see text]-stacking array in the solid state. The four-fold intermolecular hydrogen bonding interactions between the meso-nitrogen atom of the diazaporphyrin core and the ortho-hydrogen atom of the phenyl substituent dominate the crystal packing arrangement. The present study revealed that the meso-nitrogen atom of diazaporphyrins would be used as an inherent hydrogen bonding acceptor to construct supramolecular assemblies.

DOI： 10.1142/s1088424622500997

Highly soluble Ni(II) dithienylnorcorrole 査読有り

Shiori Itabuchi, Ryo Nozawa, Takuya Yoshida, Norihito Fukui, Hiroshi Shinokubo

Journal of Porphyrins and Phthalocyanines 頁： A - E 2022年11月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：World Scientific Pub Co Pte Ltd

Recently, norcorrole Ni(II) complexes have received much attention because they exhibit peculiar solid-state structures and fascinating electronic properties originating from their distinct antiaromatic character. In this work, we have prepared a norcorrole Ni(II) complex with 5-hexylthien-2-yl substituents at the meso-positions, of which the antiaromatic nature was evaluated by <sup>1</sup>H NMR analysis as well as NICS and ACID calculations. The X-ray diffraction analysis elucidated its molecular structure and crystal packing arrangement. Crystal packing structures of Ni(II) meso-di(5-methylthien-2-yl)norcorrole and Ni(II) meso-di(5-hexylthien-2-yl)norcorrole were markedly different. The latter provided a polar crystal because of the unidirectional alignment of 5-hexylthien-2-yl groups in the solid state.

DOI： 10.1142/s1088424622500730

Realization of Stacked-Ring Aromaticity in a Water-Soluble Micellar Capsule 査読有り

Si-Yu Liu, Natsuki Kishida, Jinseok Kim, Norihito Fukui, Rie Haruki, Yasuhiro Niwa, Reiji Kumai, Dongho Kim, Michito Yoshizawa, Hiroshi Shinokubo

Journal of the American Chemical Society 2022年10月

Planarization of a bowl-shaped molecule by triple-decker stacking 査読有り

Hiroyuki Kawashima, Norihito Fukui, Quan Manh Phung, Takeshi Yanai, Hiroshi Shinokubo

Cell Reports Physical Science 3 巻 ( 9 ) 頁： 101045 - 101045 2022年9月

Nitrogen Extrusion of Diazacorrphycenes to Azacorroles and Synthesis of Two Types of Copper 10-Azacorrole Complexes 査読有り

Atsumi Yagi, Naoya Okada, Norihito Fukui, Hisaaki Tanaka, Takuji Hatakeyama, Hiroshi Shinokubo

Chemistry Letters 51 巻 ( 3 ) 頁： 321 - 324 2022年3月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：The Chemical Society of Japan

The synthesis of Pd(II) and Cu(II) 10-azacorroles with a meso-NH group has been achieved through the thermal extrusion of one nitrogen atom from the corresponding diazacorrphycene metal complexes. We also found that oxidation of the Cu(II) 10-azacorrole complex afforded another type of copper 10-azacorrole with an imine moiety. The structural, magnetic, and electrochemical properties of these compounds were investigated to disclose the nature of two types of copper 10-azacorroles.

DOI： 10.1246/cl.210777

Web of Science

Isolation and Structure Analysis of a Ni(II) Norcorrole Radical Anion 査読有り

Shusaku Ukai, Norihito Fukui, Takahisa Ikeue, Hiroshi Shinokubo

Chemistry Letters 51 巻 ( 2 ) 頁： 182 - 184 2022年2月

A Supramolecular Polymer Constituted of Antiaromatic Ni II Norcorroles 査読有り

Shusaku Ukai, Aiko Takamatsu, Masaki Nobuoka, Yusuke Tsutsui, Norihito Fukui, Soichiro Ogi, Shu Seki, Shigehiro Yamaguchi, Hiroshi Shinokubo

Angewandte Chemie International Edition 61 巻 ( 6 ) 2022年2月

<scp>d</scp>-Mannose-appended 5,15-diazaporphyrin for photodynamic therapy 査読有り

Lamiaa M. A. Ali, Kazuya Miyagawa, Norihito Fukui, M{\'{e } }lanie Onofre, Khaled El Cheikh, Alain Mor{\`{e } }re, S{\'{e } }bastien Cl{\'{e } }ment, Magali Gary-Bobo, S{\'{e } }bastien Richeter, Hiroshi Shinokubo

Organic & Biomolecular Chemistry 2022年

Antiaromatic 1,5‐Diaza‐ <i>s</i> ‐indacenes 査読有り

Kensuke Hanida, Jinseok Kim, Norihito Fukui, Yusuke Tsutsui, Shu Seki, Dongho Kim, Hiroshi Shinokubo

Angewandte Chemie International Edition 60 巻 ( 38 ) 頁： 20765 - 20770 2021年9月

Determinant Factors of Three-Dimensional Aromaticity in Antiaromatic Cyclophanes 査読有り

Hiroyuki Kawashima, Shusaku Ukai, Ryo Nozawa, Norihito Fukui, Garrett Fitzsimmons, Tim Kowalczyk, Heike Fliegl, Hiroshi Shinokubo

Journal of the American Chemical Society 143 巻 ( 28 ) 頁： 10676 - 10685 2021年7月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：American Chemical Society (ACS)

Three-dimensional aromaticity arising from the close stacking of two antiaromatic π-conjugated macrocycles has recently received considerable attention. Here, a cyclophane consisting of two antiaromatic Ni(II) norcorrole units tethered with two flexible alkyl chains was synthesized. The norcorrole cyclophane showed crystal polymorphism providing three different solid-state structures. Surprisingly, one of them adopted an aligned face-to-face stacking arrangement with negligible displacement along the slipping axis. Although the exchange repulsion between two π-clouds should be maximized in this orientation, the π–π distance is remarkably close (3.258 Å). Three-dimensional aromaticity in this conformation has been supported experimentally and theoretically as evidenced by small bond length alternations as well as the presence of a diatropic ring current. An analogous cyclophane with two aromatic Ni(II) porphyrin units was prepared for comparison. The porphyrin cyclophane exhibited a slipped-stacking conformation with a larger displacement (2.9 Å) and a larger interplanar distance (3.402 Å) without noticeable change of the aromaticity of each porphyrin unit. In solution, the norcorrole cyclophane forms a twist stacking arrangement with effective interplanar orbital overlap and exists in an equilibrium between stacked and nonstacked structures. Thermodynamic parameters of the stacking process were estimated, revealing an inherently large attractive interaction operating between two norcorrole units, which has been further supported by energy decomposition analysis.

DOI： 10.1021/jacs.1c04348

Redox-induced reversible [2+2] cycloaddition of an etheno-fused diporphyrin 査読有り

Kazuya Miyagawa, Ichiro Hisaki, Norihito Fukui, Hiroshi Shinokubo

CHEMICAL SCIENCE 12 巻 ( 14 ) 頁： 5224 - 5229 2021年4月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：ROYAL SOC CHEMISTRY

3,5-Ethenoporphyrin is a pi -extended porphyrin containing a fused ethene unit between the meso- and beta -positions, exhibiting unique contribution of macrocyclic antiaromaticity. We have recently reported that its analogue, etheno-fused diporphyrin, underwent thermal [2 + 2] cycloaddition to furnish X-shaped cyclobutane-linked tetraporphyrins. Here we demonstrate that the cyclobutane-ring formation is dynamically redox-active. Namely, the tetraporphyrin underwent two-step four-electron oxidation to afford two etheno-fused diporphyrin dications. The reduction of the resulting dication regenerated the cyclobutane-linked tetraporphyrin. The dication was sufficiently stable to allow its isolation under ambient conditions. The structure of the dication has been confirmed by H-1 NMR spectroscopy and X-ray diffraction analysis. Importantly, the simultaneous double C-C bond cleavage in the cyclopropane ring in the tetraporphyrin is exceptional among dynamic redox (dyrex) systems to achieve large structural changes, thus offering new insights for the design of novel redox-active functional organic materials for electrochromic dyes, organic batteries, and organic memories.

DOI： 10.1039/d1sc00438g

Web of Science

Synthesis and Properties of an 18 pi Aromatic Norcorrole P(V) Complex 査読有り

Takuya Yoshida, Siham Asyiqin Shafie, Hiroyuki Kawashima, Norihito Fukui, Hiroshi Shinokubo

ORGANIC LETTERS 23 巻 ( 7 ) 頁： 2826 - 2830 2021年4月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：AMER CHEMICAL SOC

[16]Norcorrole is an antiaromatic ring-contracted porphyrinoid. Here, we show that the phosphorus insertion of the free-base [16]norcorrole switches its antiaromaticity to aromaticity. The treatment of a free-base meso-dimesityl[16]norcorrole with phosphorus tribromide in pyridine afforded an [18]norcorrole P(V) complex, which exhibited porphyrin-like absorption and fluorescence spectra. The phosphorus center adopted a distorted tetragonal pyramidal coordination geometry. The distinct aromatic nature of the [18]-norcorrole P(V) complex was corroborated both experimentally and theoretically.

DOI： 10.1021/acs.orglett.1c00823

Web of Science

Dual Emission of a Free-Base 5-Oxaporphyrinium Cation from its cis- and trans-NH Tautomers 査読有り

Asahi Takiguchi, Seongsoo Kang, Norihito Fukui, Dongho Kim, Hiroshi Shinokubo

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 60 巻 ( 6 ) 頁： 2915 - 2919 2021年2月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：WILEY-V C H VERLAG GMBH

Replacement of the meso methine carbon atoms of porphyrins with heteroatoms is a powerful strategy for tuning their optical and electronic properties. In particular, 5-oxaporphyrin is an attractive target due to its importance as an intermediate in heme catabolism. In this work, we describe the synthesis and properties of a free-base 5-oxaporphyrinium cation, which was prepared by the ring-closure of a bilindione with trifluoromethanesulfonic anhydride. This free-base 5-oxaporphyrinium cation exhibits dual fluorescence originating from its unique NH tautomerism. In contrast to normal porphyrins, the cis form of the 5-oxaporphyrinium cation is more stable than the trans form due to the effective delocalization of its positive charge. We thus demonstrate here that meso-modified heteroporphyrins enable the manipulation of NH tautomerism in porphyrinic macrocycles.

DOI： 10.1002/anie.202013542

Web of Science

Synthesis and electron-transport properties of a stable antiaromatic Ni-II norcorrole with the smallest meso-substituent 査読有り

Shusaku Ukai, Yun Hee Koo, Norihito Fukui, Shu Seki, Hiroshi Shinokubo

DALTON TRANSACTIONS 49 巻 ( 41 ) 頁： 14383 - 14387 2020年11月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：ROYAL SOC CHEMISTRY

meso-Dimethylnorcorrole Ni-II complex exhibited enough stability under ambient conditions despite the distinct antiaromaticity. The small methyl substituents realized a dense and long-range p-stacking in its solid state, which resulted in the superior electron-transporting ability to previously reported Ni-II norcorroles.

DOI： 10.1039/d0dt03143g

Web of Science

Reactions of Antiaromatic Norcorrole Ni(II) Complex with Carbenes 査読有り

Si-Yu Liu, Takaki Fukuoka, Norihito Fukui, Ji-Young Shin, Hiroshi Shinokubo

ORGANIC LETTERS 22 巻 ( 11 ) 頁： 4400 - 4403 2020年6月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：AMER CHEMICAL SOC

Norcorrole is a ring-contracted porphyrinoid, exhibiting distinct antiaromaticity. Herein, we report the reactions of meso-dimesitylnorcorrole Ni(II) complex with two types of carbenes: dichlorocarbene and an N-heterocyclic carbene (NHC). The reaction with in-situ-generated dichlorocarbene resulted in the double insertion of two chloromethine units to provide a mixture of 5,15-dichloroporphyrin and chlorinated isopyricorroles. The nucleophilic NHC attacked the 3-position of the norcorrole core and the subsequent proton transfer furnished a nonconjugated macrocycle incorporating a diazafulvene segment.

DOI： 10.1021/acs.orglett.0c01402

Web of Science

A 2-to-2 ' 18-to-18 ' doubly linked Ni(ii) norcorrole dimer: an effectively conjugated antiaromatic dyad 査読有り

Si-Yu Liu, Hiroyuki Kawashima, Norihito Fukui, Hiroshi Shinokubo

CHEMICAL COMMUNICATIONS 56 巻 ( 50 ) 頁： 6846 - 6849 2020年6月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：ROYAL SOC CHEMISTRY

The synthesis and properties of a 2-to-2 ' 18-to-18 ' doubly linked Ni(ii) norcorrole dimer are described. It adopts a highly planar structure, resulting in effective electronic interactions between the constituent norcorrole units. Nevertheless, each norcorrole unit exhibits substantial antiaromaticity, which stands in sharp contrast to stacked norcorrole dimers.

DOI： 10.1039/d0cc02543g

Web of Science

Synthesis and properties of 5-aza-15-thiaporphyrins 査読有り

Yamashita D, Omori H, Fukui N, Shinokubo H

Journal of Porphyrins and Phthalocyanines 24 巻 ( 1-3 ) 頁： 84 - 89 2020年1月

5,5,15,15-Tetraoxo-5,15-Dithiaporphyrin as a Highly Electron-Deficient Porphyrinic Ligand 査読有り

Atsumi Yagi, Takeshi Kondo, Daisuke Yamashita, Naruhiko Wachi, Hiroto Omori, Norihito Fukui, Takahisa Ikeue, Hiroshi Shinokubea

CHEMISTRY-A EUROPEAN JOURNAL 25 巻 ( 68 ) 頁： 15580 - 15585 2019年12月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：WILEY-V C H VERLAG GMBH

Oxidation of 5,15-dithiaporphyrin with meta-chloroperbenzoic acid afforded the corresponding S,S-tetraoxide in good yield. The resultant 5,5,15,15-tetraoxo-5,15-dithiaporphyrin exhibited the highly electron-deficient nature as elucidated by the electrochemical analysis and theoretical calculations. Treatment of tetraoxodithiaporphyrin with zinc(II) acetate and nickel(II) acetate provided the corresponding metal complexes efficiently. Owing to its enhanced Lewis acidity of the metal center by the electron-deficient ligand, the nickel complex underwent facile axial ligation to form pentacoordinate and hexacoordinate high-spin (S=1) complexes in solution and solid, respectively. The binding constant of pyridine to the Ni-II center was significantly higher than those of conventional porphyrin Ni-II complexes. Temperature-dependent magnetic susceptibility measurements of the high-spin Ni-II complex revealed the presence of weak ferromagnetic interactions.

DOI： 10.1002/chem.201903639

Web of Science

Synthesis of meso-Alkyl-Substituted Norcorrole-Ni-II Complexes and Conversion to 5-Oxaporphyrins(2.0.1.0) 査読有り

Si-Yu Liu, Hiroko Tanaka, Ryo Nozawa, Norihito Fukui, Hiroshi Shinokubo

CHEMISTRY-A EUROPEAN JOURNAL 25 巻 ( 32 ) 頁： 7618 - 7622 2019年6月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：WILEY-V C H VERLAG GMBH

The synthesis of antiaromatic Ni-II-norcorroles having primary, secondary, and tertiary alkyl groups at the reactive meso-positions was attempted. Reductive coupling of a Ni-II-dipyrrin precursor provided Ni-II-meso-dihexylnorcorrole, which underwent substantial degradation on silica gel. Introduction of tert-butyl groups was unsuccessful due to the difficult preparation of the corresponding dipyrrin precursor. Meanwhile, Ni-II-norcorroles with isopropyl and cyclohexyl groups were isolated as stable molecules under ambient conditions. Furthermore, we found that oxidation of Ni-II-meso-dialkylnorcorroles with hydrogen peroxide in the presence of sodium carbonate gave Ni-II-5-oxaporphyrins(2.0.1.0). In contrast, oxidation of Ni-II-meso-dimesitylnorcorrole under the same reaction conditions gave 10-oxaporphyrin(1.1.1.0). The contrasting reactivity can be attributed to the steric congestion around the meso-positions.

DOI： 10.1002/chem.201901292

Web of Science

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