Pi-Conjugated Molecule Based Supramolecular Nanofibers Whose Structures and Functions Can Be Reversibly Switched by External Stimuli

2013 Fiscal Year Final Research Report

• Project/Area Number: 24651117
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Single-year Grants
• Research Field: Nanostructural science
• Research Institution: Osaka University
• Principal Investigator: MIYATA Mikiji 大阪大学, 産業科学研究所, 招へい教授 (90029322)
• Co-Investigator(Kenkyū-buntansha): HISAKI Ichiro 大阪大学, 大学院工学研究科, 助教 (90419466)
• Co-Investigator(Renkei-kenkyūsha): TOHNAI Norimitsu 大阪大学, 大学院工学研究科, 准教授 (30346184)
• Project Period (FY): 2012-04-01 – 2014-03-31
• Keywords: 超分子化学 / ナノファイバー / デヒドロベンゾアヌレン / 双極子‐双極子相互作用 / 刺激応答性 / 超分子ゲル

Research Abstract

Supramolecular nanofibers (SNFs) composed of pi-conjugated molecules exhibit attractive optical and electrical properties, which are attributed to their high-aspect-ratio morphology. Generally, such SNFs have been constructed with molecules that have flexible long chains in the periphery. However, such flexibility often causes molecular disorder that decreases the functionality of SNFs. On the other hand, we successfully achieved crystalline SNFs with dehydrobenzoannulene derivatives that have two methyl ester groups at non-centrosymmetric positions. Moreover, we found that the SNF experiences structural transformation with keeping its fibrous morphology upon irradiation of ultrasound. Interestingly, the transformation brings drastic changes of a charge carrier behavior of the SNF.

Research Products

• [Journal Article] Crystalline Supramolecular Nanofibers Based on Dehydrobenzoannulene Derivatives (2013)
  • Author(s): Hajime Shigemitsu, Ichiro Hisaki, Eriko Kometani, Daisuke Yasumiya, Yuu Sakamoto, Keisuke Osaka, Tejender S. Thakur, Akinori Saeki, Shu Seki, Fumiko Kimura, Tsunehisa Kimura, Norimitsu Tohnai and Mikiji Miyata
  • Journal Title: Chem. Eur. J Volume: 19 Pages: 15366-15377
  • DOI: 10.1002/chem.201301967
  • Peer Reviewed
• [Journal Article] Ultrasound Triggered Structural Conversion of Supramolecular Nanofibers Associated with Drastic Change of Electric Property (2013)
  • Author(s): Hajime Shigemitsu, Ichiro Hisaki, Hirofumi Senga, Daisuke Yasumiya, Tejender S. Thakur, Akinori Saeki, Shu Seki, Kazunori Nakano, Norimitsu Tohnai and Mikiji Miyata
  • Journal Title: Chem. Asian J Volume: 8 Pages: 1372-1376
  • DOI: 10.1002/asia.201300258
  • Peer Reviewed
• [Journal Article] Inclusion Crystals of 3a,7a,12a,24-Tetrahydroxycholane with Haloaromatic Compounds : Pitches and Stability of Herringbone Assemblies in Channels (2013)
  • Author(s): Wen-Tzu Liu, Yute Kin, Kazunori Nakano, Ichiro Hisaki, Norimitsu Tohnai, and Mikiji Miyata
  • Journal Title: Chem. Lett Volume: 42 Pages: 143-145
  • DOI: 10.1246/cl.2013.143
  • Peer Reviewed
• [Journal Article] Guest-Dependent Structural Transformation of Dehydrobenzoannulene Inclusion Crystals Composed ofπ-Stacked Parallelogram Columnar Motifs (2012)
  • Author(s): Hajime Shigemitsu, Ichiro Hisaki, Eriko Kometani, Norimitsu Tohnai, Mikiji Miyata
  • Journal Title: Chem. Lett Volume: 41 Pages: 1535-1537
  • DOI: 10.1246/cl.2012.1535
  • Peer Reviewed
• [Journal Article] Halogen Bond Effect on Bundling of Hydrogen Bonded 2-Fold Helical Columns (2012)
  • Author(s): Toshiyuki Sasaki, Ichiro Hisaki, Seiji Tsuzuki, Norimitsu Tohnai and Mikiji Miyata
  • Journal Title: CrystEngComm Volume: 14 Pages: 5749-5752
  • DOI: 10.1039/C2CE26081F
  • Peer Reviewed
• [Journal Article] Crystal Structure of Quinine : Unignorable Affects of Vinyl and Methoxy Groups on Molecular Assemblies of Cinchona Alkaloids (2012)
  • Author(s): Ichiro Hisaki, Eri Hiraishi, Toshiyuki Sasaki, Hideo Orita, Seiji Tsuzuki, Norimitsu Tohnai, and Mikiji Miyata
  • Journal Title: Chem. Asian J Volume: 7 Pages: 2607-2614
  • DOI: 10.1002/asia.201200566
  • Peer Reviewed
• [Presentation] Crystalline Supramolecular Nanofibers Based on Dehydrobenzo- annulene Derivatives (2014)
  • Author(s): Ichiro Hisaki
  • Organizer: 日本化学会第94春季年会(Asian International Symposium on Organic Crystals)
  • Place of Presentation: 名古屋
  • Year and Date: 2014-03-29
  • Invited
• [Presentation] Solid-state Supramolecular Assemblies Based on Dehydrobenzo- annulene (2013)
  • Author(s): Ichiro Hisaki
  • Organizer: China-Japan Joint Symposium on Functional Supramolecular Architectures
  • Place of Presentation: 蘇州、中国
  • Year and Date: 2013-10-27
  • Invited
• [Presentation] 超音波による高結晶性超分子ナノファイバーの動的構造変換および電気的特性変化 (2013)
  • Author(s): 重光孟
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 滋賀
  • Year and Date: 2013-03-24
• [Presentation] アリール置換によるオクタデヒドロ[12]アヌレンの積層構造制御 (2013)
  • Author(s): 久木一朗
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 滋賀
  • Year and Date: 2013-03-24
• [Presentation] Construction of One-Dimensionallyπ-Stacked Assemblies with Inclusion Channels Using Triangular Dehydrobenzoannulenes (2012)
  • Author(s): Hajime Shigemitsu
  • Organizer: The 12th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-12)
  • Place of Presentation: 京都
  • Year and Date: 2012-11-13
• [Presentation] Highly Crystalline One- dimensional Supramolecular Assemblies Based on Polar Dehydrobenzoannulene Derivatives (2012)
  • Author(s): 重光孟
  • Organizer: 第61回高分子学会年次大会
  • Place of Presentation: 横浜
  • Year and Date: 2012-05-31
• [Book] ゲルの安定性と機能付与・次世代への応用開発 (2013)
  • Author(s): 久木一朗、藤内謙光、宮田幹二
  • Total Pages: 552
  • Publisher: 技術情報協会
• [Remarks]
  • URL: http://www.mls.eng.osaka-u.ac.jp/~mol_rec/