synthesis of chiral organosilane compounds for high performance CPL materials

• Project/Area Number: 15K05604
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Organic and hybrid materials
• Research Institution: The University of Tokyo
• Principal Investigator: Yamanoi Yoshinori 東京大学, 大学院理学系研究科(理学部), 准教授 (20342636)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Project Status: Completed (Fiscal Year 2017)
• Budget Amount: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000); Fiscal Year 2017: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000); Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2015: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
• Keywords: 円偏光発光 / 不斉ケイ素原子 / 有機ケイ素 / パラジウム触媒 / ピレン / アントラセン / 光学活性

Outline of Final Research Achievements

Compounds exhibiting circularly polarized luminescence are expected to be used as luminescent materials for three-dimensional displays. In this study, we synthesized an optically active silicon compound having both good fluorescence quantum yield and circular polarized luminescence characteristics in a monomolecular state, based on a new asymmetric silicon atom construction method. In particular, the optically active tertiary silane having a pyrene skeleton exhibited a very high value in the monomolecular state as the circular polarized luminescence characteristic glum: 0.01.

Research Products

• [Journal Article] Aggregation-Induced Emission Enhancement from Disilane-Bridged Donor-Acceptor-Donor Luminogens Based on the Triarylamine Functionality (2018)
  • Author(s): Usuki Tsukasa、Shimada Masaki、Yamanoi Yoshinori、Ohto Tatsuhiko、Tada Hirokazu、Kasai Hidetaka、Nishibori Eiji、Nishihara Hiroshi
  • Journal Title: ACS Appl. Mater. Interfaces Volume: in press Issue: 15 Pages: 12164-12172
  • DOI: 10.1021/acsami.7b14802
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Attachment chemistry of aromatic compounds on a Silicon(100) surface (2018)
  • Author(s): Henriksson Anders、Nishiori Daiki、Maeda Hiroaki、Miyachi Mariko、Yamanoi Yoshinori、Nishihara Hiroshi
  • Journal Title: Surface Science Volume: 669 Pages: 140-144
  • DOI: 10.1016/j.susc.2017.11.017
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Multifunctional Octamethyltetrasila[2.2]cyclophanes: Conformational Variations, Circularly Polarized Luminescence, and Organic Electroluminescence (2017)
  • Author(s): Shimada Masaki、Yamanoi Yoshinori、Ohto Tatsuhiko、Pham Song-Toan、Yamada Ryo、Tada Hirokazu、Omoto Kenichiro、Tashiro Shohei、Shionoya Mitsuhiko、Hattori Mineyuki、Jimura Keiko、Hayashi Shigenobu、Koike Hikaru、Iwamura Munetaka、Nozaki Koichi、Nishihara Hiroshi
  • Journal Title: J. Am. Chem. Soc. Volume: 139 Issue: 32 Pages: 11214-11221
  • DOI: 10.1021/jacs.7b05671
  • Peer Reviewed
• [Journal Article] Photocurrent generation of reconstituted photosystem II on self-assembled gold film (2017)
  • Author(s): Miyachi, M.; Ikehira, S.; Nishiori, D.; Yamanoi, Y.;* Yamada, M.; Iwai, M.; Tomo, T.; Allakhverdiev, S. I.; Nishihara, H.*
  • Journal Title: Langmuir Volume: 33 Issue: 6 Pages: 1351-1358
  • DOI: 10.1021/acs.langmuir.6b03499
  • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] Unusual reactivity of group 14 hydrides toward organic halides: synthetic studies and application to functional materials (2016)
  • Author(s): Shimada, M.; Yamanoi, Y.; Nishihara, H.
  • Journal Title: J. Synth. Org. Chem. Jpn. Volume: 74 Pages: 1098-1107
  • NAID: 130005433324
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Effects of Substitution on Solid-State Fluorescence in 9-Aryl-9-methyl-9H-9-silafluorenes (2016)
  • Author(s): *Yoshinori Yamanoi, Takayuki Nakashima, Masaki Shimada, Hiroaki Maeda, *Hiroshi Nishihara
  • Journal Title: Molecules Volume: 21 Issue: 9 Pages: 1173-1173
  • DOI: 10.3390/molecules21091173
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Effective Method for Micro-Patterning Arene-Terminated Monolayers on a Si(111) Electrode (2016)
  • Author(s): Yoshinori Yamanoi, Tetsuhiro Kobayashi, Hiroaki Maeda, Mariko Miyachi, Masato Ara, Hirokazu Tada, and Hiroshi Nishihara
  • Journal Title: Langmuir Volume: 32 Issue: 27 Pages: 6825-6829
  • DOI: 10.1021/acs.langmuir.6b01370
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Cross-Sectional TEM Analysis of an ITO Surface Coated with Photosystem I and Molecular Wires (2016)
  • Author(s): Miyachi, M.; Yamanoi, Y.;* Tomo, T.; Nishihara, H.*
  • Journal Title: J. Inorg. Organomet. Polym. Mater. Volume: 2016 Issue: 6 Pages: 1309-1312
  • DOI: 10.1007/s10904-016-0396-5
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Bright Solid-State Emission of Disilane-Bridged Donor-Acceptor-Donor and Acceptor-Donor-Acceptor Chromophores (2016)
  • Author(s): M. Shimada, M. Tsuchiya, R. Sakamoto, Y. Yamanoi, E. Nishibori, K. Sugimoto, H. Nishihara
  • Journal Title: Angew. Chem. Int. Ed. Volume: 55 Issue: 9 Pages: 3022-3026
  • DOI: 10.1002/anie.201509380
  • Peer Reviewed
• [Journal Article] Fluorescence and phosphorescence of a series of silicon-containing six-membered-ring molecules (2016)
  • Author(s): T. Nakashima, M. Shimada, Y. Kurihara, M. Tsuchiya, Y. Yamanoi, E. Nishibori, K. Sugimoto, H. Nishihara
  • Journal Title: J. Organomet. Chem. Volume: 805 Pages: 27-33
  • DOI: 10.1016/j.jorganchem.2015.12.042
  • Peer Reviewed
• [Journal Article] Synthesis, Characterization, and Physical Properties of Oligo(1-(N,N-dimethylamino)pyrrole)s and Their Doped Forms, Precursors of Candidates for Molecular Flat-band Ferromagnets (2015)
  • Author(s): Y. Yamanoi, K. Takahashi, T. Hamada, N. Ohshima, M. Kurashina, Y. Hattori, T. Kusamoto, R. Sakamoto, M. Miyachi, and H. Nishihara
  • Journal Title: Journal of Materials Chemistry C Volume: 3 Issue: 17 Pages: 1-1
  • DOI: 10.1039/c4tc02941k
  • Peer Reviewed / Acknowledgement Compliant
• [Presentation] The development of tetrasila[2.2]cyclophane derivatives for solid-state emission，electroluminescence，and circularly polarized luminescence (2017)
  • Author(s): 島田真樹，山野井慶徳，大戸達彦，山田亮，Pham Song-Toan，夛田博一，小池ひかる，岩村宗高，野崎浩一，西原寛
  • Organizer: 2017年光化学討論会
• [Presentation] Synthesis and physical properties of tetrasila[2.2]thiophenophane derivatives for the luminescent and chiroptical materials (2017)
  • Author(s): Masaki Shimada，Yoshinori Yamanoi，Kenichiro Omoto，Shohei Tashiro，Mitsuhiko Shionoya，Tatsuhiko Ohto，Song-Toan Pham，Ryo Yamada，Hirokazu Tada，Mineyuki Hattori，Keiko Jimura，Shigenobu Hayashi，Hikaru Koike，Munetaka Iwamura，Koichi Nozaki，Hiroshi Nishihara
  • Organizer: 254th ACS National Meeting & Exposition
  • Int'l Joint Research
• [Presentation] 固体発光・円偏光発光を示すオクタメチルテトラシラ[2.2]シクロファンの創製 (2017)
  • Author(s): 島田真樹，山野井慶徳，小池ひかる，岩村宗高，野崎浩一，西原寛
  • Organizer: 第21回ケイ素化学シンポジウム
• [Presentation] 不斉ケイ素原子をもつ化合物の効率的合成法の開発とその光物性 (2016)
  • Author(s): 古賀信哉・植木修平・島田真樹・山野井慶徳・湯浅順平・河合壯・打田孝明・岩村宗高・野﨑浩一・西原寛
  • Organizer: 第20回ケイ素化学協会シンポジウム
  • Place of Presentation: 安芸グランドホテル（広島県廿日市市）
  • Year and Date: 2016-10-07
• [Presentation] Effective Solid-state Emission of Disilane-bridged Arenes Including Donor and Acceptor Moieties (2015)
  • Author(s): Masaki Shimada, Ryota Sakamoto, Yoshinori Yamanoi, Hiroshi Nishihara
  • Organizer: Pacifichem 2015
  • Place of Presentation: Honolulu, HI, USA
  • Year and Date: 2015-12-17
  • Int'l Joint Research
• [Presentation] シリコン電極上にSi-アリール結合で修飾したフェロセン誘導体の電子移動挙動 (2015)
  • Author(s): 和田慶祐、前田啓明、小林徹大、宮地麻里子、山野井慶徳、西原寛
  • Organizer: 分子アーキテクトニクス研究会 第6回研究会
  • Place of Presentation: 京都大学桂キャンパスローム記念館（京都府、京都市）
  • Year and Date: 2015-10-23
• [Presentation] 固体蛍光材料・非線型光学材料に向けたドナー・アクセプター型ジアリールジシラン類の創製 (2015)
  • Author(s): 島田真樹, 山野井慶徳, 近藤高志, 松下智紀, 西堀英治, 畠山あかり, 杉本邦久, 西原 寛
  • Organizer: 日本化学会秋季事業 第5回CSJ化学フェスタ
  • Place of Presentation: タワーホール船堀（東京都、江戸川区）
  • Year and Date: 2015-10-15
• [Presentation] シリコン電極上にSi-アリール結合で修飾したフェロセン誘導体の電子移動挙動 (2015)
  • Author(s): 和田慶祐、前田啓明、小林徹大、宮地麻里子、山野井慶徳、西原寛
  • Organizer: 2015年電気化学会秋季大会
  • Place of Presentation: 埼玉工業大学（埼玉県、深谷市）
  • Year and Date: 2015-09-11
• [Remarks] 東京大学大学院理学系研究科化学専攻無機化学研究室
  • URL: https://www.chem.s.u-tokyo.ac.jp/users/inorg/link.html
• [Remarks] 東京大学 大学院理学系研究科 化学専攻 無機化学研究室
  • URL: https://www.chem.s.u-tokyo.ac.jp/~inorg/
• [Remarks] 東京大学大学院理学系研究科化学専攻無機化学研究室
  • URL: http://www.chem.s.u-tokyo.ac.jp/users/inorg/index.html