Synthesis of partial structural motifs of chiral graphene nanoribbons

2013 Fiscal Year Final Research Report

• Project/Area Number: 24655133
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Single-year Grants
• Research Field: Functional materials chemistry
• Research Institution: Ehime University
• Principal Investigator: NAKAE Takahiro 愛媛大学, 理工学研究科, 助教 (20505995)
• Project Period (FY): 2012-04-01 – 2014-03-31
• Keywords: 多環式芳香族炭化水素 / ナノグラフェン / グラフェンナノリボン / 有機半導体 / PAH

Research Abstract

Graphene nanoribbons (GNRs) are promising future semiconductor materials. To achieve GNR synthesize with high quality, a bottom-up method is demanded. We explored new methodology to obtain chiral-type nanographene materials from simple starting polycyclic aromatic hydrocarbons.
We achieved (1) synthesis of polycyclic aromatic hydrocarbons(PAHs) using AuCl catalyst, (2) synthesis of a new starting PAHs, which is a candidate for chiral-type GNR synthesis, (3) synthesis of the soluble T-shaped biazulene molecules without flexible substituents.

Research Products

• [Journal Article] Bisarylation of 1,1′,3,3′-Tetrahalo-2,2′- biazulene Under Suzuki–Miyaura Cross-Coupling Conditions (2014)
  • Author(s): T. Nakae, T. Kikuchi, S. Mori, T. Okujima, T. Murafuji, H. Uno
  • Journal Title: Chem. Lett. Volume: 43(4) Pages: 504-506
  • DOI: 10.1246/cl.131142
  • Peer Reviewed
• [Journal Article] Yellow NIR dye : π-Fused bisbenzoBODIPYs with electron-withdrawing groups (2014)
  • Author(s): M. Nakamura, M. Kitatsuka, K. Takahashi, T. Nagata, S. Mori, D. Kuzuhara, T. Okujima, H. Yamada, T. Nakae, H. Uno
  • Journal Title: Org. Biomol. Chem. Volume: 12(8) Pages: 1309-1317
  • DOI: 10.1039/C3OB41996G
  • Peer Reviewed
• [Journal Article] Study on Hinsberg thiophene synthesis of 4,8-dihydro-4,8-ethanobenzo[1,2-c;4,5- c']dithiophene (2014)
  • Author(s): K. Tagawa, S. Mori, T. Nakae, T. Okujima, H. Uno
  • Journal Title: Heterocycles Volume: 88(1) Pages: 453-462
  • DOI: 10.3987/COM-13-S(S)53
  • Peer Reviewed
• [Journal Article] Synthesis and molecular structure of cyclo[8](9,10- dihydro-9,10-anthraceno)pyrrole (2014)
  • Author(s): T. Okujima, C. Ando, S. Mori, T. Nakae, Yamada, H. Uno
  • Journal Title: Heterocycles Volume: 88(1) Pages: 417-424
  • DOI: 10.3987/COM-13-S(S)42
  • Peer Reviewed
• [Journal Article] Skeletal Reorganization of Enynes Catalyzed by a Ru(II)-Ru(III) Mixed Valence Complex Under an Atmosphere of O2 or CO (2013)
  • Author(s): T. Nakae, M. Kamiya, T. Yasunaga, Y. Fukumoto, N. Chatani
  • Journal Title: Chem. Lett. Volume: 42(12) Pages: 1565-1567
  • DOI: 10.1246/cl.130785
  • Peer Reviewed
• [Journal Article] Acenaphthylene-fused cyclo[8]pyrroles with intense NIR region absorption bands (2013)
  • Author(s): T. Okujima, C. Ando, J. Mack, S. Mori, Hisaki, T. Nakae, H. Yamada, K. Ohara, N. Kobayashi, H. Uno
  • Journal Title: Chem. Eur. J. Volume: 19(41) Pages: 13970-13978
  • DOI: 10.1002/chem.201301294
  • Peer Reviewed
• [Journal Article] Synthesis, structure and properties of ethyl naphth[2,3-f]isoindole-1- carboxylate (2013)
  • Author(s): A. Seike, K. Yamagami, Y. Kakitani, M. Kuwajima, H. Uoyama, S. Nagaoka, T. Nakae, S. Mori, T. Okujima, H. Uno
  • Journal Title: RCS Adv. Volume: 3(9) Pages: 3006-3016
  • DOI: 10.1039/c2ra22870j
  • Peer Reviewed
• [Journal Article] Width-Controlled Sub-nanometer Graphene Nanoribbon Films Synthesized by Radical-Polymerized Chemical Vapor Deposition
  • Author(s): H. Sakaguchi, Y. Kawagoe, Y. Hirano, T. Iruka, M. Yano, T. Nakae
  • Journal Title: Adv. Mater. Volume: (Published online)
  • DOI: 10.1002/adma.201305034
  • Peer Reviewed
• [Presentation] 2ゾーンCVD法による幅制御した極細グラフェンナノリボンの合成 (2014)
  • Author(s): 小島崇寛,平野善崇,矢野真葵,坂口浩司,中江隆博
  • Organizer: 電気化学会第81回大会
  • Place of Presentation: 吹田(1B25)
  • Year and Date: 20140329-31
• [Presentation] ラジカル重合型化学気相成長法によるsub-1 nm幅グラフェンナノリボンの表面合成 (2014)
  • Author(s): 矢野真葵,平野善崇,小島崇寛,中江隆博,坂口浩司
  • Organizer: 日本化学会第94春季年会
  • Place of Presentation: 名古屋(3C7-15)
  • Year and Date: 20140327-30
• [Presentation] ベンゾおよびナフト縮環ビアズレン分子の合成と特性 (2014)
  • Author(s): 中江隆博,菊地貴志,森重樹,奥島鉄雄,宇野英満,村藤俊宏
  • Organizer: 日本化学会第94春季年会
  • Place of Presentation: 名古屋(1A2-12)
  • Year and Date: 20140327-30
• [Presentation] 塩化金触媒をもちいる環化反応を利用した[5]ヘリセン類縁体の合成 (2014)
  • Author(s): 中江隆博,北畑吉晴,森重樹,奥島鉄雄,宇野英満
  • Organizer: 日本化学会第94春季年会
  • Place of Presentation: 名古屋(1A2-11)
  • Year and Date: 20140327-30
• [Presentation] ヨードエチニル基に対するAuCl触媒の高効率環化反応を利用した[5]ヘリセン類の合成 (2013)
  • Author(s): 北畑吉晴,中江隆博,森重樹,奥島鉄雄,宇野英満
  • Organizer: 第7回有機π電子シンポジウム
  • Place of Presentation: 高崎(PB16)
  • Year and Date: 20131213-14
• [Presentation] T字型縮環ビアズレン化合物の合成とその特性 (2013)
  • Author(s): 中江隆博,菊地貴志,森重樹,奥島鉄雄,宇野英満,村藤俊宏
  • Organizer: 第7回有機π電子シンポジウム
  • Place of Presentation: 高崎(PA16)
  • Year and Date: 20131213-14
• [Presentation] 極細炭素細線の低真空ボトムアップ合成法の開発 (2013)
  • Author(s): 中江隆博,坂口浩司
  • Organizer: 日本化学会中国四国支部大会若手特別講演
  • Place of Presentation: 東広島
  • Year and Date: 20131117-18
• [Presentation] 分子細線グラフェンナノリボンの低真空ボトムアップ合成法の開発 (2013)
  • Author(s): 中江隆博,坂口浩司
  • Organizer: 錯体化学会第63回討論会
  • Place of Presentation: 沖縄
  • Year and Date: 20131102-04
• [Presentation] 2,2'-ビアズレン拡張T字型分子の合成 (2013)
  • Author(s): 菊地貴志,中江隆博,森重樹,奥島鉄雄,宇野英満,村藤俊宏
  • Organizer: 第24回基礎有機化学討論会
  • Place of Presentation: 東京(2P145)
  • Year and Date: 20130905-07
• [Presentation] Skeletal Reorganization of Enynes Catalyzed by a Ru(II)-Ru(III) Mixed Valence Complex under an Atmosphere of O_2 and CO (2013)
  • Author(s): Takahiro Nakae, Tomohiko Yasunaga, Motonobu Kamiya, Yoshiya Fukumoto, Naoto Chatani
  • Organizer: International Symposium on Olefin Metathesis and related Chemistry (ISOM XX)
  • Place of Presentation: Nara, Japan
  • Year and Date: 20130714-19
• [Presentation] Bottom-Up Synthesis of Graphene Nanoribbons from Halogenated Polycyclic Aromatic Hydrocarbons at Extremely Low-Vacuum Condition (2013)
  • Author(s): Takahiro Nakae, Maki Yano, Hiroshi Sakaguchi
  • Organizer: Challenges in Organic Materials & Supramolecular Chemistry (ISACS10)
  • Place of Presentation: Kyoto, Japan
  • Year and Date: 20130618-21
• [Presentation] Synthesis of T-Shape naphthalene-fused biazulene molecule, and its properties (2013)
  • Author(s): Takahiro Nakae, Takashi Kikuchi, Shigeki Mori, Tetsuo Okujima, Toshihiro Murafuji, Hidemitsu Uno
  • Organizer: The 11th International Symposium on Functional Pi‐electron systems (Fπ11)
  • Place of Presentation: Arcachon, France
  • Year and Date: 20130602-07
• [Presentation] Bisarylation of Tetrahalobiazulene by Suzuki Reaction (2013)
  • Author(s): Takahiro, Nakae, Takashi, Kikuchi, Shigeki, Mori, Tetsuo, Okujima, Toshihiro, Murafuji, Hidemitsu, Uno
  • Organizer: The 11th International Symposium on Functional Pi‐electron systems (Fπ11)
  • Place of Presentation: Arcachon, France
  • Year and Date: 20130602-07
• [Presentation] 塩化金(I)触媒を用いたハロゲン化フェナセン類の合成 (2013)
  • Author(s): 北畑吉晴,大西竜二,中江隆博,森重樹,奥島鉄雄,宇野英満,坂口浩司
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 草津(3PB-074)
  • Year and Date: 20130322-25
• [Presentation] キラルグラフェンナノリボン構造モチーフ分子の合成 (2013)
  • Author(s): 杉村卓哉,矢野真葵,中江隆博,森重樹,奥島鉄雄,宇野英満,坂口浩司
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 草津(3PB-073)
  • Year and Date: 20130322-25
• [Presentation] テトラブロモビアズレンのビスアリール化反応および環化反応の検討 (2013)
  • Author(s): 菊地貴志,中江隆博,森重樹,奥島鉄雄,宇野英満,村藤俊宏
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 草津(3PB-048)
  • Year and Date: 20130322-25
• [Presentation] Synthesis of T-shaped Naphthalene-Fused Biazulene molecule (2013)
  • Author(s): 中江隆博
  • Organizer: 山形大学テニュアトラック国際シンポジウムInternational Workshop on Coordination Compounds
  • Place of Presentation: 山形
  • Year and Date: 2013-09-27
• [Presentation] 電気化学エピタキシャル重合により作製したグラフェンナノリボンのSTM観察 (2012)
  • Author(s): 山元朋毅,仲淵龍,萩原宏紀,矢野真葵,中江隆博,坂口浩司
  • Organizer: 第61回高分子討論会
  • Place of Presentation: 名古屋(3O10)
  • Year and Date: 20120919-21
• [Presentation] 多環芳香族化合物の塩化金(I)触媒を用いる多点環化反応による高収率合成 (2012)
  • Author(s): 北畑吉晴,大西竜二,中江隆博,森重樹,奥島鉄雄,宇野英満,坂口浩司
  • Organizer: 第59回有機金属化学討論会
  • Place of Presentation: 吹田(P3C-31)
  • Year and Date: 20120913-15
• [Presentation] Synthesis of Iodinated Fused Aromatics by Multiple Cyclization using AuCl Catalyst (2012)
  • Author(s): Takahiro Nakae, Ryuji Ohnishi, Yoshiharu Kitahata, Hisako Sato, Shigeki Mori, Tetsuo Okujima, Hidemitsu Uno, Hiroshi Sakaguchi
  • Organizer: The 6th International Conference on Gold Science, Technology and its Applications (GOLD2012)
  • Place of Presentation: 東京(1P-026)
  • Year and Date: 20120905-08
• [Remarks] 愛媛大学理学部化学科有機化学研究室
  • URL: http://chem.sci.ehime-u.ac.jp/~orgchem1