Faculty Profiles - SHINOKUBO, Hiroshi

Papers - SHINOKUBO, Hiroshi

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Antiaromatic 1,5‐Diaza‐ s ‐indacenes Reviewed International coauthorship International journal

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

Angewandte Chemie International Edition Vol. 60 ( 38 ) page： 20765 - 20770 2021.9

Synthesis of Tetrasilatetrathia[8]circulenes through C-I and C-H Silylation Invited Reviewed International journal

Akahori Shuhei, Fujihara Tetsuaki, Tsuji Yasushi, Shinokubo Hiroshi, Miyake Yoshihiro

Vol. 53 ( 17 ) page： 2995 - 3000 2021.9

Determinant Factors of Three-Dimensional Aromaticity in Antiaromatic Cyclophanes Reviewed International coauthorship International journal

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

Journal of the American Chemical Society Vol. 143 ( 28 ) page： 10676 - 10685 2021.7

Non‐Planar Perylene Bisimide Analogues with Inserted Carbonyl and Methylene Subunits Reviewed International journal

Mai Odajima, Keita Tajima, Norihito Fukui, Hiroshi Shinokubo

Angewandte Chemie International Edition Vol. 60 ( 29 ) page： 15838 - 15843 2021.7

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

The synthesis and properties of dinaphthotropone bisimide (DNTrBI) and dinaphthocycloheptatriene bisimide (DNCHepBI) are described. Their molecular design is conceptually based on the insertion of a carbon atom into a perylene bisimide (PBI) core. These molecules adopt non-planar structures due to the presence of a seven-membered ring. The PBI derivative into which a carbonyl group was inserted (DNTrBI) immediately underwent nonradiative decay and/or intersystem crossing in its excited state. The PBI derivative into which a methylene group was inserted (DNCHepBI) was susceptible to deprotonation on account of the two electron-withdrawing naphthalene monoimide units. Subsequent aerobic oxidation resulted in the formation of a C-C bond at the central methylene unit, thus affording a sigma-dimer. The formation of this C-C bond is dynamically redox-active, i.e., electron injection into the sigma-dimer almost quantitatively regenerated the deprotonated DNCHepBI.

DOI： 10.1002/anie.202104882

Acridino[2,1,9,8‐ klmna ]acridine Bisimides: An Electron‐Deficient π‐System for Robust Radical Anions and n‐Type Organic Semiconductors Reviewed International journal

Keita Tajima, Kyohei Matsuo, Hiroko Yamada, Shu Seki, Norihito Fukui, Hiroshi Shinokubo

Angewandte Chemie International Edition Vol. 60 ( 25 ) page： 14060 - 14067 2021.6

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

We report the synthesis and properties of acridino[2,1,9,8-klmna]acridine bisimide (AABI), a nitrogen-doped anthanthrene with two imide functionalities. AABI exhibits excellent electron affinity as evident by its low-lying LUMO level (-4.1 eV vs. vacuum). Single-electron reduction of one AABI derivative afforded the corresponding radical anion, which was stable under ambient conditions. Photoconductivity measurements suggest that the intrinsic electron mobility of an N-phenethyl AABI derivative obeys a band-transport model. Accordingly, an electron mobility of 0.90 cm(2) V-1 s(-1) was attained with the corresponding single-crystal organic field-effect transistor (OFET) device. The vacuum-deposited OFET device consisting of a polycrystalline sample exhibited high electron mobility of up to 0.27 cm(2) V-1 s(-1) even in air. This study demonstrates that dual incorporation of both imide substituents and imine-type nitrogen atoms is an effective strategy to create novel electron-deficient pi-systems.

DOI： 10.1002/anie.202102708

Synthesis and Characterization of 16 pi Antiaromatic 2,7-Dihydrodiazapyrenes: Antiaromatic Polycyclic Hydrocarbons with Embedded Nitrogen Reviewed International journal

Nakazato, Takumi, Takekoshi, Haruka, Sakurai, Takahiro, Shinokubo, Hiroshi, Miyake, Yoshihiro

Angewandte Chemie International Edition Vol. 60 ( 25 ) page： 13877 - 13881 2021.6

Quadruply BN‐Fused Tetrathia[8]circulenes with Flexible Frameworks: Synthesis, Structures and Properties Reviewed International journal

Shuhei Akahori, Takahiro Sasamori, Hiroshi Shinokubo, Yoshihiro Miyake

Chemistry – A European Journal Vol. 27 ( 31 ) page： 8178 - 8184 2021.6

Iron hexamesityl-5,15-diazaporphyrin: synthesis, structure and catalytic use for direct oxidation of sp(3) C-H bonds Reviewed International journal

Vol. 50 ( 18 ) page： 6343 - 6348 2021.5

Cationic Nickel(II) Pyridinophane Complexes: Synthesis, Structures and Catalytic Activities for C–H Oxidation Reviewed International journal

Nishimura Tsubasa, Ando Yuki, Shinokubo Hiroshi, Miyake Yoshihiro

Chemistry Letters Vol. 50 ( 5 ) page： 1049 - 1052 2021.5

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

<p>A series of nickel(II) pyridinophane complexes were synthesized and characterized by X-ray crystallographic analysis. Their IR spectra supported the existence of mononuclear nickel(II) complexes in solution. Furthermore, we conducted catalytic C–H oxidation of cyclooctane with nickel(II) pyridinophanes as the catalysts. The activity of nickel(II) pyridinophanes was affected by steric hindrance around the nitrogen atoms.</p>

DOI： 10.1246/cl.210074

Web of Science

Scopus

Redox-induced reversible [2 + 2] cycloaddition of an etheno-fused diporphyrin Reviewed International journal

Kazuya Miyagawa, Ichiro Hisaki, Norihito Fukui, Hiroshi Shinokubo

Chemical Science Vol. 12 ( 14 ) page： 5224 - 5229 2021.4

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

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

Synthesis and Properties of an 18π Aromatic Norcorrole P(V) Complex Reviewed International journal

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

Organic Letters Vol. 23 ( 7 ) page： 2826 - 2830 2021.4

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：American Chemical Society ({ACS})

[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

Enthalpically and Entropically Favorable Self-Assembly: Synthesis of C-4h-Symmetric Tetraazatetrathia[8]circulenes by Regioselective Introduction of Pyridine Rings Reviewed

Akahori Shuhei, Sasamori Takahiro, Shinokubo Hiroshi, Miyake Yoshihiro

CHEMISTRY-A EUROPEAN JOURNAL Vol. 27 page： 5675 - 5682 2021.3

Peripherally Arylated 2,8-Diazaperylenes from Anthracene Diimide: Synthesis and Oxidative Annulation Reviewed

Takahiro Sakurai, Takumi Nakazato, Hiroshi Shinokubo, and Yoshihiro Miyake

Organic Letters Vol. 23 ( 6 ) page： 2099 - 2103 2021.3

Dinaphtho[1,8-bc:1 ',8 '-fg][1,5]dithiocine Bisimide Invited Reviewed

Tanaka Yuki, Tajima Keita, Fukui Norihito, Shinokubo Hiroshi

ASIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 10 ( 3 ) page： 541 - 544 2021.2

Dual Emission of a Free-Base 5-Oxaporphyrinium Cation from its cis- and trans-NH Tautomers Reviewed International coauthorship

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

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Vol. 60 ( 6 ) page： 2915 - 2919 2021.2

Complexation of 2,7-diazapyrene with boron for structural and electronic tuning Reviewed

Nakazato Takumi, Shinokubo Hiroshi, Miyake Yoshihiro

CHEMICAL COMMUNICATIONS Vol. 57 ( 3 ) page： 327 - 330 2021.1

Dual-ion charge–discharge behaviors of Na–NiNc and NiNc–NiNc batteries Reviewed International journal

Jinkwang Hwang, Rika Hagiwara, Hiroshi Shinokubo, Ji-Young Shin

Materials Advances Vol. 2 ( 7 ) page： 2263 - 2266 2021

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

<p>Dual-ion Na–organic batteries were provided with anti-aromatic NiNc, exposing inherent charge–discharge behavior with high discharge capacity, high durability, and high Coulombic efficiency with high-density currents.</p>

DOI： 10.1039/D1MA00007A

Web of Science

Scopus

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Hetero[8]circulenes: synthetic progress and intrinsic properties Invited Reviewed

Miyake Yoshihiro, Shinokubo Hiroshi

CHEMICAL COMMUNICATIONS Vol. 56 ( 100 ) 2020.12

Aggregation-Induced Emission in Tetrathia[8]circulene Octaoxides via Restriction of the Dynamic Motion of their Negatively Curved pi-Frameworks Reviewed

Murase Hiroyasu, Nagata Yuya, Akahori Shuhei, Shinokubo Hiroshi, Miyake Yoshihiro

CHEMISTRY-AN ASIAN JOURNAL Vol. 15 ( 22 ) page： 3873 - 3877 2020.11

Site-selective halogenation on meso-mesityl substituents of 10,20-dimesityl-5,15-diazaporphyrins with an AuX3/AgOTf combination Reviewed

Longevial Jean-Francois, Miyagawa Kazuya, Shinokubo Hiroshi

DALTON TRANSACTIONS Vol. 49 ( 42 ) page： 14786 - 14789 2020.11

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Papers - SHINOKUBO, Hiroshi