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Development of Super Lewis Acid Chemistry Based on Two-Coordinate Boron Cation

Research Project

Project/Area Number 26708004
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypePartial Multi-year Fund
Research Field Organic chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

Shoji Yoshiaki  東京工業大学, 科学技術創成研究院, 准教授 (40525573)

Research Collaborator FUKUSHIMA Takanori  
TANAKA Naoki  
HASHIZUME Daisuke  
Project Period (FY) 2014-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥24,440,000 (Direct Cost: ¥18,800,000、Indirect Cost: ¥5,640,000)
Fiscal Year 2016: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2015: ¥6,890,000 (Direct Cost: ¥5,300,000、Indirect Cost: ¥1,590,000)
Fiscal Year 2014: ¥13,780,000 (Direct Cost: ¥10,600,000、Indirect Cost: ¥3,180,000)
Keywordsホウ素 / ボリニウムイオン / ルイス酸 / 超ルイス酸 / 小分子活性化 / ホールドーピング / ナノカーボン / 薄膜材料 / カーボンナノチューブ / グラフェン / ジボラン / ナノカーボン類 / カルボラン / 二酸化炭素 / 二硫化炭素
Outline of Final Research Achievements

In this study, we succeeded in the first isolation and large-scale synthesis of Mes2B+, which is a 2-coordinated boron cation (= borinium ion) bonded only with aromatic groups. This class of compound had been thought to be too unstable to isolate. By using Mes2B+, we developed a variety of unique small-molecule activation reactions including unprecedented C=O double bond cleavage reaction of carbon dioxide. Furthermore, we found that Mes2B+ serves as an excellent hole dopant for carbon nanotubes and transition metal dicarcoconide-based thin film materials. These findings will provide a foundation for a new "super Lewis acid molecule chemistry" based on isolatable super Lewis acid molecules.

Report

(5 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Annual Research Report
  • 2015 Annual Research Report
  • 2014 Annual Research Report
  • Research Products

    (41 results)

All 2018 2017 2016 2015 2014 Other

All Int'l Joint Research (2 results) Journal Article (10 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 8 results,  Open Access: 3 results,  Acknowledgement Compliant: 6 results) Presentation (28 results) (of which Int'l Joint Research: 5 results,  Invited: 15 results) Remarks (1 results)

  • [Int'l Joint Research] Ottawa University(カナダ)

    • Related Report
      2016 Annual Research Report
  • [Int'l Joint Research] Ottawa University(カナダ)

    • Related Report
      2015 Annual Research Report
  • [Journal Article] Chemical hole doping into large-area transition metal dichalcogenide monolayers using boron-based oxidant2018

    • Author(s)
      Hirofumi Matsuoka, Kaito Kanahashi, Naoki Tanaka, Yoshiaki Shoji, Lain‐Jong Li, Jiang Pu, Hiroshi Ito, Takanori Fukushima, Taishi Takenobu
    • Journal Title

      Japanese Journal of Applied Physics

      Volume: 57 Issue: 2S2 Pages: 1-4

    • DOI

      10.7567/jjap.57.02cb15

    • NAID

      210000148662

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Formation of an Isolable Divinylborinium Ion and Diphenylacetylene2017

    • Author(s)
      Naoki Tanaka, Yoshiaki Shoji, Daisuke Hashizume, Manabu Sugimoto, Takanori Fukushima
    • Journal Title

      Angewandte Chemie, International Edition

      Volume: 56 Issue: 19 Pages: 5312-5316

    • DOI

      10.1002/anie.201701730

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Remarkably air- and moisture-stable hole-doped carbon nanotube films by a boron-based oxidant2017

    • Author(s)
      K. Funahashi, N. Tanaka, Y. Shoji, N. Imazu, K. Nakayama, K. Kanahashi, H. Shirae, S. Noda, H. Ohta, T. Fukushima, and T. Takenobu
    • Journal Title

      Appl. Phys. Express

      Volume: 10 Issue: 3 Pages: 035101-035101

    • DOI

      10.7567/apex.10.035101

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Unveiling a new aspect of simple arylboronic esters: long-lived room-temperature phosphorescence from heavy-atom-free molecules2017

    • Author(s)
      Y. Shoji, Y. Ikabata, Q. Wang, D. Nemoto, A. Sakamoto, N. Tanaka, J. Seino, H. Nakai, T. Fukushima
    • Journal Title

      Journal of the American Chemical Society

      Volume: 139 Issue: 7 Pages: 2728-2733

    • DOI

      10.1021/jacs.6b11984

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Convenient Route to Monocarba-closo-dodecaborate Anions2016

    • Author(s)
      N. Tanaka, Y. Shoji, T. Fukushima
    • Journal Title

      Organometallics

      Volume: 35 Issue: 11 Pages: 2022-2025

    • DOI

      10.1021/acs.organomet.6b00309

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] 11B Solid-State NMR Interaction Tensors of Linear Two-Coordinate Boron: The Dimesitylborinium Cation2015

    • Author(s)
      A. E. Alain, Y. Shoji, T. Fukushima, D. L. Bryce
    • Journal Title

      Inorganic Chemistry

      Volume: 54 Issue: 24 Pages: 11889-11896

    • DOI

      10.1021/acs.inorgchem.5b02161

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] The molecular and electronic structures of a thioaroyl cation formed by borinium ion-mediated C=S double bond cleavage of CS22015

    • Author(s)
      Y. Shoji, N. Tanaka, D. Hashizume, T. Fukushima
    • Journal Title

      Chem. Commun.

      Volume: 51 Issue: 69 Pages: 13342-13345

    • DOI

      10.1039/c5cc05645d

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] 「超ルイス酸分子」ジアリールボリニウムイオンの合成、構造および反応性2015

    • Author(s)
      庄子良晃
    • Journal Title

      月刊ファインケミカル

      Volume: 2月号 Pages: 59-65

    • Related Report
      2014 Annual Research Report
  • [Journal Article] A two-coordinate boron cation featuring C-B(+)-C bonding2014

    • Author(s)
      Y. Shoji, N. Tanaka, K. Mikami, M. Uchiyama and T. Fukushima
    • Journal Title

      Nature Chem.

      Volume: 6 Issue: 6 Pages: 498-503

    • DOI

      10.1038/nchem.1948

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] “Simple and Strong” ジアリールボリニウムイオンの開発 ―「超ルイス酸分子科学」の開拓へ向けて2014

    • Author(s)
      庄子良晃, 田中直樹, 福島孝典
    • Journal Title

      月刊化学

      Volume: 69 Pages: 38-42

    • Related Report
      2014 Annual Research Report
  • [Presentation] ホウ素の特性を活かした電子・光電子機能性材料の創製2018

    • Author(s)
      庄子良晃
    • Organizer
      第2回 東工大応用化学系 次世代を担う若手シンポジウム
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] テトラアリールジボラン(4)誘導体の溶液および固体状態における二重蛍光発光2018

    • Author(s)
      田中直樹・庄子良晃・酒井隼人・羽曾部卓・五十幡康弘・王祺・中井浩巳・福島孝典
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] テトラアリールジボラン(4)誘導体の特異な発光挙動2017

    • Author(s)
      田中 直樹, 庄子 良晃, 杉本 学, 福島 孝典
    • Organizer
      日本化学会 第97春季年会
    • Place of Presentation
      慶応大学日吉キャンパス, 神奈川県
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] ホウ素と芳香環で組み立てる分子機能の探求2017

    • Author(s)
      庄子良晃
    • Organizer
      ITbM/IGER Chemistry Workshop 2017
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] プロペラ分子が可能にする高秩序有機薄膜の造形と機能2017

    • Author(s)
      庄子良晃
    • Organizer
      第3回「高次複合光応答」若手の会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 電子欠損性ホウ素化合物の新構造・新反応の探求2017

    • Author(s)
      庄子良晃
    • Organizer
      第49回構造有機化学若手の会 夏の学校
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 電子欠損性ホウ素化合物の新構造・新反応2017

    • Author(s)
      庄子良晃
    • Organizer
      第5回慶応有機化学若手シンポジウム
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 水・空気に安定な新規テトラアリールジボラン(4)の合成と二重蛍光発光挙動2017

    • Author(s)
      田中直樹・庄子良晃・福島孝典
    • Organizer
      第44回有機典型元素化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] テトラメシチルジボラン(4) の固体蛍光クロミズム2017

    • Author(s)
      田中直樹・庄子良晃・福島孝典
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 電子欠損性ホウ素化合物による新物質変換反応2016

    • Author(s)
      庄子良晃
    • Organizer
      第4回アライアンス若手研究交流会
    • Place of Presentation
      北海道大学電子科学研究所, 北海道
    • Year and Date
      2016-11-09
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Novel Molecular Transformations Using Highly Electron-Deficient Boron Compounds2016

    • Author(s)
      Yoshiaki Shoji
    • Organizer
      11th International Conference of Cutting-Edge Organic Chemistry in Asia (ICCEOCA-11/ARNCEOCA-2)
    • Place of Presentation
      KAIST, Daegeon, Korea
    • Year and Date
      2016-10-27
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] テトラメシチルジボラン(4)の合成と特異な発光特性2016

    • Author(s)
      田中 直樹, 庄子 良晃, 杉本 学, 福島 孝典
    • Organizer
      第27回基礎有機化学討論会
    • Place of Presentation
      広島国際会議場, 広島県
    • Year and Date
      2016-09-01
    • Related Report
      2016 Annual Research Report
  • [Presentation] 二配位ホウ素カチオンによるアセチレン誘導体の活性化反応2016

    • Author(s)
      田中 直樹, 庄子 良晃, 橋爪 大輔, 福島 孝典
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス, 京都府
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Environmentally Stable Carrier Doping into Carbon Nanotube Films by Extraordinary Molecular Lewis Acid2016

    • Author(s)
      舟橋 一真, 田中 直樹, 庄子 良晃, 中山 航, 金橋 魁利, 白江 宏之, 野田 優, 福島 孝典, 竹延 大志
    • Organizer
      第50回フラーレン・ナノチューブ・グラフェン総合シンポジウム
    • Place of Presentation
      東京大学 伊藤国際学術研究センター, 東京
    • Year and Date
      2016-02-19
    • Related Report
      2015 Annual Research Report
  • [Presentation] Environmentally Stable Carrier Doping into Graphene Films by Extraordinary Molecular Lewis Acid2016

    • Author(s)
      Environmentally Stable Carrier Doping into Carbon Nanotube Films by Extraordinary Molecular Lewis Acid
    • Organizer
      第50回フラーレン・ナノチューブ・グラフェン総合シンポジウム
    • Place of Presentation
      東京大学 伊藤国際学術研究センター, 東京
    • Year and Date
      2016-02-19
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthesis, Structure, and Reactivity of Novel Electron-Deficient Boron Compounds2016

    • Author(s)
      庄子良晃
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス, 京都府
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] Electronic Structure and Reactivity of Unprecedented Two-Coordinate Boron Cation with C-B+-C Bonding2016

    • Author(s)
      Yoshiaki Shoji
    • Organizer
      12th International Conference of Computational Methods in Science and Engineering (ICCMSE-2016)
    • Place of Presentation
      Metropolitan Hotel, Athens, Greece
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis, structure, and reactivity of the first isolable diarylborinium ion2015

    • Author(s)
      Naoki Tanaka, Yoshiaki Shoji, Takanori Fukushima
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Hawaii, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 二配位ホウ素カチオンの高いルイス酸性と親カルコゲン性を利用した小分子活性化反応2015

    • Author(s)
      田中直樹, 庄子良晃, 橋爪大輔, 福島孝典
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛大学城北キャンパス・松山大学カルフールホール, 愛媛県
    • Year and Date
      2015-09-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthesis, Structure, and Reactivity of Two-Coordinate Boron Cation with C-B+-C Bonding2015

    • Author(s)
      Yoshiaki Shoji
    • Organizer
      The 1st International Symposium on π-System Figuration
    • Place of Presentation
      Osaka University Nakanoshima Center, Osaka
    • Year and Date
      2015-04-30
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] ボリニウムイオンによる炭素―カルコゲン二重結合切断反応2015

    • Author(s)
      田中直樹, 庄子良晃, 福島孝典
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス(千葉県船橋市)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 新規ホウ素反応活性種の創製と新反応開発2015

    • Author(s)
      庄子良晃
    • Organizer
      日本化学会関東支部栃木地区講演会
    • Place of Presentation
      宇都宮大学, 栃木県
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] Synthesis, Structure, and Reactivity of Diarylborinium Ions2015

    • Author(s)
      Yoshiaki Shoji
    • Organizer
      Symposium on Organometallics and Organic Synthesis
    • Place of Presentation
      東京工業大学大岡山キャンパス, 東京
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis, Structure, and Reactivity of Two-Coordinate Boron Cation with C-B+-C Bonding2015

    • Author(s)
      Yoshiaki Shoji
    • Organizer
      The 1st International Symposium on π-System Figuration
    • Place of Presentation
      大阪大学中之島センター, 大阪府
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Development of Boron-based Molecular Super Lewis Acid2014

    • Author(s)
      Yoshiaki Shoji
    • Organizer
      International Symposium on Integrated Molecular/Materials Science and Engineering (IMSE2014)
    • Place of Presentation
      Liuyuan Hotel, Nanjing, China
    • Year and Date
      2014-11-01 – 2014-11-03
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 二配位ホウ素カチオンの創製:超ルイス酸分子化学の開拓へ向けて2014

    • Author(s)
      庄子良晃
    • Organizer
      第一回資源研フォーラム
    • Place of Presentation
      東京工業大学 大岡山キャンパス(東京都目黒区)
    • Year and Date
      2014-10-21 – 2014-10-22
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 物質の新形態に基づく新機能・新現象を求めて ―化学結合から分子集合体まで―2014

    • Author(s)
      庄子良晃
    • Organizer
      有機元素化学セミナー
    • Place of Presentation
      中央大学理工学部応用化学科(東京都文京区)
    • Year and Date
      2014-09-27
    • Related Report
      2014 Annual Research Report
  • [Presentation] ボリニウムイオンの合成、構造、および反応性2014

    • Author(s)
      田中直樹, 庄子良晃, 福島孝典
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学(宮城県仙台市)
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Annual Research Report
  • [Remarks] ホウ素による分子性超ルイス酸の開発

    • URL

      http://www.res.titech.ac.jp/news/reserch/post_32.html

    • Related Report
      2014 Annual Research Report

URL: 

Published: 2014-04-04   Modified: 2019-03-29  

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