Synthesis of novel sphericalπ-electron systems toward development of functional materials

2011 Fiscal Year Final Research Report

• Project/Area Number: 22750039
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Organic chemistry
• Research Institution: Kyoto University
• Principal Investigator: MURATA Michihisa 京都大学, 化学研究所, 助教 (30447932)
• Project Period (FY): 2010 – 2011
• Keywords: フラーレン / 構造有機化学 / 有機薄膜太陽電池 / 電子受容材料 / 有機半導体

Research Abstract

Fullerene derivatives have occupied a dominant position in bulk heterojunction(BHJ) solar cells as n-type organic semiconductors. In this work, we developed a method to modify theσ-frameworks of C60 and succeeded in the preparation of three types of skeletally-transformed fullerenes 4, 5, and 6 with distinct LUMO levels. We also evaluated the performance in the BHJ solar cells consisting of the C60 derivative and poly(3-hexylthiophene)(P3HT) as the acceptor and the donor materials, respectively. The electrochemical measurements showed that 6 has the highest LUMO level due to the transformation of one of the carbonyl groups. As a result, 6 : P3HT cell marked the highest open-circuit voltage(Voc) of 0. 74 V, which is 20% higher than that of the cell using the benchmark acceptor material PCBM(Voc=0. 60 V).

Research Products

• [Journal Article] (2011)
  • Author(s): M. Murata, Y. Morinaka, Y. Murata, O. Yoshikawa, T. Sagawa, and S. Yoshikawa
  • Journal Title: Chem. Commun Volume: 47 Pages: 7335-7337
  • DOI: DOI:10.1039/C1CC12406D
  • Peer Reviewed
• [Journal Article] (2010)
  • Author(s): A. J. Horsewill1, S. Rols, M. R. Johnson, Y. Murata, M. Murata, K. Komatsu, M. Carravetta, S. Mamone, M. H. Levitt, J. Y.-C. Chen, J. A. Johnson, X. Lei, and N. J. Turro
  • Journal Title: Phys. Rev. B Volume: 82(8) Pages: 081410
  • DOI: DOI:10.1103/PhysRevB.82.081410
  • Peer Reviewed
• [Journal Article] (2010)
  • Author(s): Y. Li, X. Lei, S. Jockusch, J. Y.-C. Chen, M. Frunzi, J. A. Johnson, R. G. Lawler, Y. Murata, M. Murata, K. Komatsu, and N. J. Turro
  • Journal Title: J. Am. Chem. Soc Volume: 132(12) Pages: 4042-4043
  • DOI: DOI:10.1021/ja910282p
  • Peer Reviewed
• [Journal Article] (2010)
  • Author(s): M. Murata, Y. Morinaka, K. Kurotobi, K. Komatsu, and Y. Murata
  • Journal Title: Chem. Lett Volume: 39(3) Pages: 298-299
  • DOI: DOI:10.1246/cl.2010.298
  • Peer Reviewed
• [Journal Article] (2010)
  • Author(s): Y. Morinaka, F. Tanabe, M. Murata, Y. Murata and K. Komatsu
  • Journal Title: Chem. Commun Volume: 46 Pages: 4532-4534
  • DOI: DOI:10.1039/C0CC00113A
  • Peer Reviewed
• [Journal Article] Molecular Surgery toward Organic Synthesis of Endohedral Fullerenes (2010)
  • Author(s): M. Murata, Y. Murata, K. Komatsu
  • Journal Title: Chemistry of anocarbons Pages: 215-237
• [Presentation] 有機色素の直結したアザフラーレンの合成と光物性 (2012)
  • Author(s): 村田理尚・勝谷郷史・村田靖次郎・大久保敬・福住俊一
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶應義塾大学
  • Year and Date: 20120325-28
• [Presentation] 17員環開口部をもつ新規フラーレン誘導体の合成と性質 (2012)
  • Author(s): 櫻井悠子・村田理尚・黒飛敬・若宮淳志・村田靖次郎
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶應義塾大学
  • Year and Date: 20120325-28
• [Presentation] ダンベル型フラーレン誘導体の合成と光電変換特性 (2012)
  • Author(s): 登政博・村田理尚・若宮淳志・佐川尚・吉川暹・村田靖次郎
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶應義塾大学
  • Year and Date: 20120325-28
• [Presentation] リチウムアセチリドを用いた1, 2-フラーレン誘導体の合成と有機太陽電池特性 (2011)
  • Author(s): 登政博・村田理尚・森中裕太・若宮淳志・佐川尚・吉川暹・村田靖次郎
  • Organizer: 第22回基礎有機化学討論会
  • Place of Presentation: つくば
  • Year and Date: 20110921-23
• [Presentation] BODIPY-アザフラーレン連結分子の合成と物性 (2011)
  • Author(s): 勝谷郷史・村田理尚・村田靖次郎・大久保敬・福住俊一
  • Organizer: 第22回基礎有機化学討論会
  • Place of Presentation: つくば
  • Year and Date: 20110921-23
• [Presentation] Spherical Aromaticity of Fullerene Dianions Studied with Endohedral Dihydrogen as NMR Probe (2011)
  • Author(s): M. Nobori, M. Murata, Y. Murata
  • Organizer: 第41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: 首都大学東京
  • Year and Date: 20110905-07
• [Presentation] Synthesis and Properties of Azafullerene-BODIPY Dyads (2011)
  • Author(s): M. Murata, S. Katsuya, Y. Murata, K. Ohkubo, and S. Fukuzumi
  • Organizer: 14th International Symposium on Novel Aromatic Compounds(ISNA-14)
  • Place of Presentation: Eugene, Oregon, USA
  • Year and Date: 20110724-29
• [Presentation] Modification of theσ-Framework of[60] Fullerene for Bulk-heterojunction Solar Cells (2011)
  • Author(s): Y. Morinaka, M. Murata, Y. Murata, O. Yoshikawa, T. Sagawa, and S. Yoshikawa
  • Organizer: 14th International Symposium on Novel Aromatic Compounds(ISNA-14)
  • Place of Presentation: Eugene, Oregon, USA
  • Year and Date: 20110724-29
• [Presentation] アルキニル[60]フラーレン誘導体の合成と有機太陽電池への応用 (2011)
  • Author(s): 登政博・村田理尚・森中裕太・若宮淳志・佐川尚・吉川暹・村田靖次郎
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学
  • Year and Date: 20110326-29
• [Presentation] BODIPY-アザフラーレン連結分子の合成と物性 (2011)
  • Author(s): 勝谷郷史・村田理尚・村田靖次郎
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学
  • Year and Date: 20110326-29
• [Presentation] σ骨格が変換されたC60誘導体の有機薄膜太陽電池特性 (2011)
  • Author(s): 森中裕太・村田理尚・村田靖次郎・吉川整・佐川尚・吉川暹
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学
  • Year and Date: 20110326-29
• [Presentation] Transformation ofσ-Framework of[60] Fullerene for Bulk Hetero-Junction SolarCells (2011)
  • Author(s): M. Murata, Y. Morinaka, Y. Murata, O. Yoshikawa, T. Sagawa, and S. Yoshikawa
  • Organizer: 第1回統合物質国際シンポジウム
  • Place of Presentation: 北海道
  • Year and Date: 20110124-25
• [Presentation] Reaction of Cage-opened Fullerene Derivative with Grignard Reagents and Subsequent Transannular Cyclization (2010)
  • Author(s): Y. Morinaka, M. Murata, K. Kurotobi, K. Komatsu, Y. Murata
  • Organizer: The 2010International Chemical Congress of Pacific Basin Societies(Pacifichem)
  • Place of Presentation: Honolulu, Hawaii, USA
  • Year and Date: 20101215-20
• [Presentation] Molecular Surgery of Fullerenes and Development of New Acceptors for Organic Photovoltaic Devices (2010)
  • Author(s): M. Murata, Y. Morinaka, Y. Murata, O. Yoshikawa, T. Sagawa, and S. Yoshikawa
  • Organizer: Japan-Taiwan Joint Symposium on Innovative Synthesis for New Materials Chemistry
  • Place of Presentation: Kyoto University
  • Year and Date: 20101203-07
• [Presentation] 開口フラーレンの構造変換と有機薄膜太陽電池への応用 (2010)
  • Author(s): 森中裕太・村田理尚・村田靖次郎・吉川整・佐川尚・吉川暹
  • Organizer: 第21回基礎有機化学討論会
  • Place of Presentation: 名古屋大学
  • Year and Date: 20100909-11
• [Presentation] 内包水素分子をNMRプローブとするフラーレンC70の磁気的性質に関する研究 (2010)
  • Author(s): 登政博・村田理尚・小松紘一・村田靖次郎
  • Organizer: 第21回基礎有機化学討論会
  • Place of Presentation: 名古屋大学
  • Year and Date: 20100909-11
• [Presentation] アザフラレニルカチオンのピロールへの求電子置換反応 (2010)
  • Author(s): 勝谷郷史・村田理尚・村田靖次郎
  • Organizer: 第21回基礎有機化学討論会
  • Place of Presentation: 古屋大学
  • Year and Date: 20100909-11
• [Presentation] フラーレンの分子手術と有機薄膜太陽電池への展開 (2010)
  • Author(s): 村田理尚・森中裕太・登政博・村田靖次郎・小松紘一・吉川整・佐川尚・吉川暹
  • Organizer: CREST有機太陽電池シンポジウム
  • Place of Presentation: 京都大学
  • Year and Date: 20100716-17
• [Remarks]
  • URL: http://rdb.kuicr.kyoto-u.ac.jp/researchers/view/murata+michihisa