Faculty Profiles - SHINOKUBO, Hiroshi

Papers - SHINOKUBO, Hiroshi

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新形式の芳香族化合物の合成を目指して Reviewed International journal

忍久保洋

化学と教育 Vol. 68 ( 6 ) page： 268 - 269 2020.6

Authorship：Corresponding author Language：Japanese Publishing type：Research paper (scientific journal) Publisher：公益社団法人日本化学会

<p>反芳香族化合物は不安定な化合物であるが，それを上下に接近させて重ねると芳香族化合物になり，安定化することが分かってきた。これまで，芳香族性の起源は二次元的なπ電子の広がりであると考えられてきた。しかし最新の研究により，2つの分子の間の三次元的なπ電子の広がりによっても芳香族性が生じることが示された。また，反芳香族化合物が芳香族化合物よりも互いに接近しやすいことも分かってきた。分子が近づいて電荷が移動しやすくなるため，有機半導体などへの応用が期待される。</p>

DOI： 10.20665/kakyoshi.68.6_268

CiNii Research

Reactions of Antiaromatic Norcorrole Ni(II) Complex with Carbenes Reviewed

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

ORGANIC LETTERS Vol. 22 ( 11 ) page： 4400 - 4403 2020.6

Synthesis and Crystal Packing Structures of 2,7-Diazapyrenes with Various Alkyl Groups at 1,3,6,8-Positions Reviewed

Nakazato Takumi, Matsuda Wakana, Sakurai Tsuneaki, Seki Shu, Shinokubo Hiroshi, Miyake Yoshihiro

CHEMISTRY LETTERS Vol. 49 ( 5 ) page： 465 - 468 2020.5

Synthesis and properties of 5-aza-15-thiaporphyrins Invited Reviewed

Yamashita Daisuke, Omori Hiroto, Fukui Norihito, Shinokubo Hiroshi

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES Vol. 24 ( 1-3 ) page： 84 - 89 2020.3

Site-Selective N-Methylation of 5,15-Diazaporphyrins: Reactive Cationic Porphyrinoids that Provide Isoporphyrin Analogues Reviewed International coauthorship

Chia Wen Xi, Nishijo Mayu, Kang Seongsoo, Oh Juwon, Nishimura Tsubasa, Omori Hiroto, Longevial Jean-Francois, Miyake Yoshihiro, Kim Dongho, Shinokubo Hiroshi

CHEMISTRY-A EUROPEAN JOURNAL Vol. 26 ( 12 ) page： 2754 - 2760 2020.2

Site‐Selective N‐Methylation of 5,15‐Diazaporphyrins: Reactive Cationic Porphyrinoids that Provide Isoporphyrin Analogues Reviewed International journal

Chia Wen Xi, Nishijo Mayu, Kang Seongsoo, Oh Juwon, Nishimura Tsubasa, Omori Hiroto, Longevial Jean‐François, Miyake Yoshihiro, Kim Dongho, Shinokubo Hiroshi

Chemistry–A European Journal Vol. 26 ( 12 ) page： 2754 - 2760 2020.2

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

N‐Alkylation significantly changes the electronic and optical properties, as well as the reactivity of nitrogen‐containing π‐conjugated molecules. In this study, it is found that treating 5,15‐diazaporphyrins with methyl triflate selectively affords the corresponding N ‐methyl‐5,15‐diazaporphyrinium cations in good yield. N‐Methylation substantially alters the electronic properties and reactivity of diazaporphyrins. The electron‐accepting properties of the N ‐methyl‐5,15‐diazaporphyrinium cations are enhanced due to their lowered LUMO level. Stabilization of the LUMO energy enables regio‐ and stereoselective Diels–Alder reactions of the cationic diazaporphyrin with cyclopentadiene. N‐Methylation also enhances the acidity of the inner NH protons, and thus, allows facile deprotonation to provide nitrogen‐substituted isoporphyrin analogues with only one NH group in the central cavity.

CiNii Research

Systematic Synthesis of Tetrathia[8]circulenes: The Influence of Peripheral Substituents on the Structures and Properties in Solution and Solid States Reviewed

Kato Shohei, Akahori Shuhei, Serizawa Yuma, Lin Xu, Yamauchi Mitsuaki, Yagai Shiki, Sakurai Tsuneaki, Matsuda Wakana, Seki Shu, Shinokubo Hiroshi, Miyake Yoshihiro

JOURNAL OF ORGANIC CHEMISTRY Vol. 85 ( 1 ) page： 62 - 69 2020.1

Inserting Nitrogen: An Effective Concept To Create Nonplanar and Stimuli-Responsive Perylene Bisimide Analogues Reviewed International coauthorship

Hayakawa Sakiho, Kawasaki Ayumi, Hong Yongseok, Uraguchi Daisuke, Ooi Takashi, Kim Dongho, Akutagawa Tomoyuki, Fukui Norihito, Shinokubo Hiroshi

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Vol. 141 ( 50 ) page： 19807 - 19816 2019.12

Aggregation-Induced Emission of Nitrogen-Bridged Naphthalene Monoimide Dimers Reviewed

Tajima Keita, Fukui Norihito, Shinokubo Hiroshi

ORGANIC LETTERS Vol. 21 ( 23 ) page： 9516 - 9520 2019.12

5,5,15,15‐Tetraoxo‐5,15‐Dithiaporphyrin as a Highly Electron‐Deficient Porphyrinic Ligand Reviewed

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

Chemistry – A European Journal Vol. 25 ( 68 ) page： 15580 - 15585 2019.12

Regioselective Desilylation of a pi-Extended Aza[5]helicene

Ushiyama Ayako, Shinokubo Hiroshi, Hiroto Satoru

CHEMISTRY LETTERS Vol. 48 ( 9 ) page： 1069 - 1072 2019.9

Ni(II) 10-Boracorrole: An Antiaromatic Porphyrinoid Containing a Boron Atom at the meso-Position

Omori Hiroto, Shinokubo Hiroshi

ORGANOMETALLICS Vol. 38 ( 15 ) page： 2878 - 2882 2019.8

Soluble and Planar 2,9-Diazaperopyrenes through Reductive Aromatization of Perylene Diimides: Tunable Emission and Aggregation Behaviors

Nakamura Yasutaka, Nakazato Takumi, Kamatsuka Takuto, Shinokubo Hiroshi, Miyake Yoshihiro

CHEMISTRY-A EUROPEAN JOURNAL Vol. 25 ( 45 ) page： 10571 - 10574 2019.8

Three-dimensional aromaticity in an antiaromatic cyclophane Reviewed International coauthorship

Nozawa Ryo, Kim Jinseok, Oh Juwon, Lamping Anna, Wang Yemei, Shimizu Soji, Hisaki Ichiro, Kowalczyk Tim, Fliegl Heike, Kim Dongho, Shinokubo Hiroshi

NATURE COMMUNICATIONS Vol. 10 2019.8

Exploration of Li-Organic Batteries Using Hexaphyrin as an Active Cathode Material

Shin Ji-Young, Zhang Zhongyue, Awaga Kunio, Shinokubo Hiroshi

MOLECULES Vol. 24 ( 13 ) 2019.7

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

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

CHEMISTRY-A EUROPEAN JOURNAL Vol. 25 ( 32 ) page： 7618 - 7622 2019.6

Synthesis of Hydroxyisooxophlorins by Oxidative Degradation of meso-Hydroxyporphyrins

Takiguchi Asahi, Fukui Norihito, Shinokubo Hiroshi

ORGANIC LETTERS Vol. 21 ( 11 ) page： 3950 - 3953 2019.6

Regioselective Oxidative Ring Cleavage of Antiaromatic Nickel(II) Norcorrole to Dialkoxybis(dipyrrin)s

Shafie Siham A., Kawashima Hiroyuki, Miyake Yoshihiro, Shinokubo Hiroshi

CHEMPLUSCHEM Vol. 84 ( 6 ) page： 623 - 626 2019.6

Synthesis of Dihydropyrazine-fused Porphyrin Dimers

Takiguchi Asahi, Wakita Mana, Hiroto Satoru, Shinokubo Hiroshi

CHEMISTRY LETTERS Vol. 48 ( 4 ) page： 371 - 373 2019.4

Ni(II) 10-Phosphacorrole: A Porphyrin Analogue Containing Phosphorus at the Meso Position

Omori Hiroto, Hiroto Satoru, Takeda Youhei, Fliegl Heike, Minakata Satoshi, Shinokubo Hiroshi

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Vol. 141 ( 12 ) page： 4800 - 4805 2019.3

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Papers - SHINOKUBO, Hiroshi