Faculty Profiles - SHINOKUBO, Hiroshi

Papers - SHINOKUBO, Hiroshi

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Effect of structural bending on the photophysical properties of perylene bisimide Invited Reviewed International journal

Hikaru Sotome, Masahiro Higashi, Yuki Tanaka, Hiroshi Shinokubo, Yasuhiro Kobori, Norihito Fukui

Journal of Chemical Physics Vol. 162 ( 11 ) page： 114305 2025.3

Captodative Approach to Stable Nitrogen-Centered Radicals, Anions, and Cations Exhibiting Near-Infrared Electrochromism Reviewed International coauthorship International journal Open Access

Keita Tajima, Christophe Bucher, Daiki Shimizu, Norihito Fukui, Hiroshi Shinokubo

JACS Au 2025.3

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

DOI： 10.1021/jacsau.5c00037

Other Link： https://doi.org/10.1021/jacsau.5c00037

Synthesis and Properties of Donor-Acceptor-Type Cyclobisbiphenylenecarbonyls Reviewed International journal

Nishimoto, E; Ikai, T; Shinokubo, H; Fukui, N

CHEMISTRY-A EUROPEAN JOURNAL Vol. 31 ( 15 ) page： e202404194 2025.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Chemistry - A European Journal

The scalable synthesis of figure-eight π-systems is challenging for the conventional bottom-up approach. We have recently reported that the oxidative inner-bond cleavage of commercially available dibenzo[g,p]chrysene efficiently furnishes a figure-eight π-acceptor, cyclobisbiphenylenecarbonyl (CBBC), in large quantity. Furthermore, its donor–acceptor-type derivative with four N-carbazolyl substituents at the meta-positions of the carbonyl groups exhibited thermally activated delayed fluorescence (TADF) and circularly polarized luminescence (CPL) with a high |gCPL| value of 1.0×10−2. Herein, we synthesized nine donor–acceptor-type CBBC derivatives by changing the donor substituents and their positions. Compared to previously reported carbazole-substituted CBBC, tetramethylcarbazole- and 9,10-dihydro-9,9-dimethylacridine-substituted derivatives exhibited enhanced emission quantum yields and accelerated reverse intersystem crossing. The functionalization of the para-positions of the carbonyl groups resulted in better tunability of emission colors rather than meta-functionalization, whose color variation ranges from light blue to red. The incorporation of bulky substituents at the meta-positions of the carbonyl groups induced the conformational change to a distorted ring structure. Investigation of the substituent effect on the chiroptical properties revealed that the introduction of less bulky donor units such as carbazole at the meta-positions of the carbonyl groups is effective in achieving high |gCPL| values.

DOI： 10.1002/chem.202404194

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PubMed

Other Link： https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202404194

Diradical character view of energy stabilization in π-stacked dimers of antiaromatic molecules Reviewed International journal Open Access

Hiroshi Shinokubo

Chemistry Letters Vol. 53 ( 12 ) page： upae224 2024.12

Catalytic Construction of Stereogenic Boron Center on BODIPY via Enantioselective Suzuki–Miyaura Coupling Reviewed International journal

Aiko Kondo, Hideaki Takano, Hiroshi Shinokubo

Chemistry Letters 2024.11

Bowl-Shaped Anthracene-Fused Antiaromatic Ni(II) Norcorrole: Synthesis, Structure, Assembly with C60, and Photothermal Conversion Reviewed International journal

Kaisheng Wang, Aninda Ghosh, Daiki Shimizu, Hideaki Takano, Masatoshi Ishida, Ryohei Kishi, Hiroshi Shinokubo

Angewandte Chemie International Edition Vol. 64 ( 7 ) page： e202419289 2024.11

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

<jats:p>The synthesis of bowl‐shaped antiaromatic molecules represents a formidable challenge, because the molecular distortion further destabilizes these already inherently reactive molecules. Here, we report the synthesis and properties of bowl‐shaped fused anthrylnorcorroles that exhibit near‐infrared (NIR) absorption reaching 1900 nm. The oxidation of meso‐anthryldibromodipyrrin provides fused anthryldibromodipyrrin, which was converted to the fused mono‐ and bisanthrylnorcorroles through Ni(0)‐mediated intramolecular coupling with a bis(dibromodipyrrin) Ni(II) complex. Single‐crystal X‐ray diffraction analyses revealed bowl‐shaped structures for the fused mono‐ and bisanthrylnorcorroles, which enables them to act as suitable receptors for C60 with bonding constants of 2.89 × 103 M–1 and 1.59 × 103 M–1, respectively. The formation of a 1:1 complex between the fused monoanthrylnorcorrole and C60 was confirmed by single‐crystal X‐ray diffraction analysis. The effective expansion of the π‐conjugation through the triple fusion of the norcorrole with the anthracene units substantially enhances the near‐infrared absorption bands, which endows these anthrylnorcorroles with effective photothermal conversion.</jats:p>

DOI： 10.1002/anie.202419289

Other Link： https://onlinelibrary.wiley.com/doi/10.1002/anie.202419289

Zig-zag-fused π-extended BODIPYs via gold-catalysed cycloisomerisation Invited Reviewed International journal

Fumika Ohashi, Hideaki Takano, Hiroshi Shinokubo

Chemical Communications Vol. 60 ( 88 ) page： 12892 - 12895 2024.11

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

An efficient gold-catalysed intramolecular cycloisomerisation of BODIPYs provides seven-membered-ring-fused BODIPYs on the zig-zag edge. The fused π-extended BODIPYs exhibit unique photophysical properties including NIR absorption and emission.

DOI： 10.1039/d4cc04416a

Synthesis and electron-transporting properties of phenazine bisimides Reviewed International journal

Keita Tajima, Taito Moribe, Kyohei Matsuo, Hiroko Yamada, Shu Seki, Seiya Yokokura, Toshihiro Shimada, Norihito Fukui, Hiroshi Shinokubo

Journal of Materials Chemistry C Vol. 13 ( 2 ) page： 655 - 662 2024.10

Synthesis of four regioisomeric Ni(II) azacorroles via oxidative ring-expansion of prefunctionalised norcorroles Reviewed International coauthorship International journal

Sha Li, Shaowei Zhang, Kohei Ohtake, Hiroshi Shinokubo, Xiaofang Li

Organic Chemistry Frontiers Vol. 11 ( 20 ) page： 5928 - 5937 2024.10

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

We explored the synthesis and properties of four regioisomeric Ni(ii) azacorroles. The results revealed that the substituent at different pyrrole positions exerted different effects on the electronic structures.

DOI： 10.1039/d4qo01415d

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Inner-Bond-Cleavage Approach to Figure-Eight Macrocycles from Planar Aromatic Hydrocarbons Reviewed International coauthorship International journal

Reiji Yoshina, Junichiro Hirano, Emiko Nishimoto, Yuki Sakamoto, Keita Tajima, Shunsuke Minabe, Muhammet Uyanik, Kazuaki Ishihara, Tomoyuki Ikai, Eiji Yashima, Takuya Omine, Fumitaka Ishiwari, Akinori Saeki, Jinseok Kim, Juwon Oh, Dongho Kim, Guanting Liu, Takuma Yasuda, Hiroshi Shinokubo, Norihito Fukui

Journal of the American Chemical Society Vol. 146 ( 43 ) page： 29383 - 29390 2024.9

An n-type semiconducting diazaporphyrin-based hydrogen-bonded organic framework Reviewed International journal

Takahiro Sakurai, Tappei Tanabe, Hiroaki Iguchi, Zhuowei Li, Wakana Matsuda, Yusuke Tsutsui, Shu Seki, Ryotaro Matsuda, Hiroshi Shinokubo

Chemical Science Vol. 15 ( 32 ) page： 12922 - 12927 2024.8

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

A Ni(ii) diazaporphyrin with carboxy groups afforded a stable HOF through intermolecular hydrogen-bonding interactions, which exhibited high semiconductivity as well as stability toward heating and various solvents.

DOI： 10.1039/d4sc03455d

Other Link： https://doi.org/10.1039/D4SC03455D

Radical reactivity of antiaromatic Ni(II) norcorroles with azo radical initiators Invited Reviewed International journal

Siham Asyiqin Shafie, Ryo Nozawa, Hideaki Takano, Hiroshi Shinokubo

Beilstein Journal of Organic Chemistry Vol. 20 page： 1967 - 1972 2024.8

Ultrafine Spatial Modulation of Diazapyrene-Based Two-Dimensional Conjugated Covalent Organic Frameworks Reviewed International coauthorship International journal

Zhuowei Li, Takahiro Tsuneyuki, Rajendra Prasad Paitandi, Takumi Nakazato, Masahiro Odawara, Yusuke Tsutsui, Takayuki Tanaka, Yoshihiro Miyake, Hiroshi Shinokubo, Makito Takagi, Tomomi Shimazaki, Masanori Tachikawa, Katsuaki Suzuki, Hironori Kaji, Samrat Ghosh, Shu Seki

Journal of the American Chemical Society Vol. 146 ( 33 ) page： 23497 - 23507 2024.8

Homochiral and Heterochiral Self‐Sorting Assemblies of Antiaromatic Ni(II) Norcorrole Dimers Reviewed International journal

Si‐Yu Liu, Sha Li, Shusaku Ukai, Ryo Nozawa, Norihito Fukui, Ryota Sugimori, Ryohei Kishi, Hiroshi Shinokubo

Chemistry – A European Journal Vol. 30 ( 39 ) page： e202400292 2024.7

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

Abstract

Recently, π–π stacked antiaromatic π‐systems have received considerable attention because they can exhibit stacked‐ring aromaticity due to substantial intermolecular orbital interactions. Here, we report three antiaromatic norcorrole dimers that self‐assemble to form supramolecular architectures through chiral self‐sorting. A 2,2’‐linked norcorrole dimer with 3,5‐di‐tert‐butylphenyl groups forms a π‐stacked dimer both in solid and solution states via homochiral self‐sorting. Its association constant in solution is (3.6±1.7)×10<sup>5</sup> M<sup>−1</sup> at 20 °C. In the solid state, 3,3’‐linked norcorrole dimers with 3,5‐di‐tert‐butylphenyl and phenyl groups afford macrocyclic and helical supramolecular assemblies via heterochiral and homochiral self‐sorting, respectively. Notably, the subtle modification in the substituent resulted in a complete change in the structure of the aggregates and the chiral self‐sorting mode. The present findings demonstrate that structural manipulation in antiaromatic monomer units leads to the formation of various supramolecular assemblies on the basis of the attractive interactions between antiaromatic π‐systems.

DOI： 10.1002/chem.202400292

Synthesis of sterically congested double helicene by alkyne cycloisomerization Invited Reviewed International journal

Junichiro Hirano, Sayaka Miyoshi, Eiji Yashima, Tomoyuki Ikai, Hiroshi Shinokubo, Norihito Fukui

Chemical Communications Vol. 60 ( 47 ) page： 6035 - 6038 2024.6

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

Alkyne cycloisomerization of 2,7,10,15-tetra(ortho-alkynylphenyl)benzo[g,p]chrysene containing bulky 4-alkoxy-2,6-dimethylphenyl groups at the alkyne terminals selectively proceeded at the sterically crowded bay-region.

DOI： 10.1039/d4cc01573h

End-to-End Bent Perylene Bisimide Cyclophanes by Double Sulfur Extrusion Reviewed International journal

Yuki Tanaka, Keita Tajima, Ryota Kusumoto, Yasuhiro Kobori, Norihito Fukui, Hiroshi Shinokubo

Journal of the American Chemical Society Vol. 146 ( 23 ) page： 16332 - 16339 2024.5

Norcorroles as antiaromatic π-electronic systems that form dimension-controlled assemblies Reviewed International journal

Soh Ishikawa, Kazuhisa Yamasumi, Shinya Sugiura, Shunsuke Sato, Go Watanabe, Yun Hee Koo, Shu Seki, Yuya Bando, Yohei Haketa, Hiroshi Shinokubo, Hiromitsu Maeda

Chemical Science Vol. 15 ( 20 ) page： 7603 - 7609 2024.5

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

Norcorroles with 3,4,5-trialkoxyphenyl moieties were synthesized to form thermotropic liquid crystals (LCs), in which triple-decker stacking structures were formed. The LC state exhibited discotic columnar structures to exhibit high electric conductivity.

DOI： 10.1039/d4sc01633e

Changing aromatic properties through stacking: the face-to-face dimer of Ni(II) bis(pentafluorophenyl)norcorrole Reviewed International coauthorship International journal

Qian Wang, Dage Sundholm, Jürgen Gauss, Tommaso Nottoli, Filippo Lipparini, Shota Kino, Shusaku Ukai, Norihito Fukui, Hiroshi Shinokubo

Physical Chemistry Chemical Physics Vol. 26 ( 20 ) page： 14777 - 14786 2024.5

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

The diatropic (red) and paratropic (yellow) current density of the antiaromatic Ni(ii) bis(pentafluorophenyl)norcorrole and of its aromatic face-to-face stacked dimer.

DOI： 10.1039/d4cp00968a

Inner-bond-cleavage approach to figure-eight macrocycles from planar aromatic hydrocarbons Reviewed International journal

Journal of the American Chemical Society Vol. 146 page： 29383 - 29390 2024.5

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

<jats:p>Contemporary synthetic strategies in organic chemistry rely heavily on the stepwise formation of bonds between fragments of the target compound (‘bottom-up’ approach). Figure-eight aromatic macrocycles represent a considerable challenge for the bottom-up approach, and the lack of versatile synthetic routes to such macrocycles prevents the use of their distinctive chiral D2-symmetric structures in advanced materials. Herein, we demonstrate the oxidative cleavage of internal double bonds of planar polycyclic aromatic hydrocarbons enables the scalable, catalytic, and enantioselective synthesis of figure-eight macrocycles. These macrocycles, with incorporated carbonyl groups, serve as a chiral electron-acceptor unit to furnish a thermally activated delayed fluorescence material with efficient circularly polarized luminescence. The inner-bond-cleavage approach is thus an effective alternative to the bottom-up approach, proving access to hitherto inaccessible materials.</jats:p>

DOI： 10.26434/chemrxiv-2024-j1xxr

CiNii Research

Triply-Linked Porphyrin−Norcorrole Hybrid with Singlet Diradical Character Reviewed International coauthorship International journal

Kaisheng Wang, Satoru Ito, Shuang Ren, Daiki Shimizu, Norihito Fukui, Ryohei Kishi, Qiang Liu, Atsuhiro Osuka, Jianxin Song, Hiroshi Shinokubo

Angewandte Chemie International Edition Vol. 63 ( 16 ) page： e202401233 2024.4

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

Norcorrole Ni(II) complexes have recently received considerable attention as readily accessible antiaromatic molecules. Their high stabil-ity under ambient conditions and easy synthesis have enabled the exploration of the intrinsic properties of antiaromatic molecules. Here, we report the synthesis and properties of directly meso−meso singly-linked porphyrin−norcorrole hybrids and triply-linked porphy-rin−norcorrole hybrids. The singly-linked and triply-linked porphyrin−norcorrole hybrids were fully characterized, including their X-ray structural analysis. Because of their orthogonal conformation, singly-linked hybrids maintained the individual electronic property of por-phyrin and norcorrole subunits The triply-linked hybrid showed a significant decrease in the HOMO–LUMO gaps, the paratropic ring current in the norcorrole subunit, and the diamagnetic ring current in the porphyrin subunit. Furthermore, the triply-linked hybrid exhib-ited singlet diradical characteristics, confirmed by VT-NMR, ESR, and SQUID experiments.

DOI： 10.1002/anie.202401233

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Papers - SHINOKUBO, Hiroshi