Investigation of electronic properties of carbazole dimer and their application for novel photofunctional materials.

• Project/Area Number: 19550040
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Osaka Kyoiku University
• Principal Investigator: TANI Keita Osaka Kyoiku University, 教育学部, 教授 (60207165)
• Co-Investigator(Kenkyū-buntansha): HIGUCHI Hiroyuki 富山大学大学院, 理工学研究部, 教授 (00165094) ; OHKITA Hideo 京都大学大学院, 工学研究科, 准教授 (50301239)
• Project Period (FY): 2007 – 2008
• Project Status: Completed (Fiscal Year 2008)
• Budget Amount: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000); Fiscal Year 2008: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000); Fiscal Year 2007: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
• Keywords: カルバゾール / カルバゾロファン / 蛍光 / りん光 / エキシマー / ドナー-アクセプター / 光誘起電子移動 / 電荷移動 / カチオンラジカル二量体 / 渡環π-π相互作用 / ドナー-アクセプター系 / シクロファン / 酸化還元電位 / ドナーアクセプター

Research Abstract

光伝導性や青色発光などの興味ある光物性を有するカルバゾール発色団の二量化によって生じる電子物性を解明するために、本研究では2架橋系(1)および3架橋系のカルバゾロファン類(2)の合成を行った。(1), (2)の各種吸収スペクトルと発光スペクトルから、一重項および三重項エキシマー生成に関する知見が得られた。さらに、(1), (2)とペリレン、テレフタレートのようなアクセプター連結系を合成することもでき、これらの連結系における電荷移動相互作用や光誘起電子移動過程についても明らかにすることができた。

Research Products

• [Journal Article] Comparative Studies on ElectronicSpectra and Redox Behaviors of Isomeric Benzo[1,2-b:4,5-b#]difurans and Benzo[1,2-b:5,4-b#]difurans. (2009)
  • Author(s): N. Hayashi, Y. Saito, H. Higuchi, K.Suzuki
  • Journal Title: J. Phys. Chem. A 113 Pages: 5342-5347
  • Peer Reviewed
• [Journal Article] Synthesis and Photophysical Properties of Tris-bridged [3.3.n](3,6,9)-Carbazolophanes. (2009)
  • Author(s): K. Tani, N. Sakumoto, K. Kubono, K. Hori, Y. Tohda, H. Benten, H. Ohkita,S. Ito and M. Yamamoto
  • Journal Title: Chem. Lett. 38 Pages: 140-141
  • NAID: 10025119106
  • Peer Reviewed
• [Journal Article] Synthesis and Photophysical Properties of Tris-bridged [3.3.n](3,6,9)Carbazolophanes (2009)
  • Author(s): Keita Tani
  • Journal Title: Chemistry Letters 38
  • NAID: 10025119106
  • Peer Reviewed
• [Journal Article] A monoclinic polymorph of 4,4'-dichloro-2,2'-(piperazine-1,4-diyld imethylene)-diphenol. (2008)
  • Author(s): K. Kubono, Y. Tsuno, K. Tani and K.Yokoi
  • Journal Title: Acta Crystallographica E64, o2446
  • Peer Reviewed
• [Journal Article] 4,4'-Dichloro-2,2'-(piperazine-1,4-diyldimethylene)diphenol. (2008)
  • Author(s): K. Kubono, Y. Tsuno, K. Tani and K.Yokoi
  • Journal Title: Acta Crystallographica E64, o2309
  • Peer Reviewed
• [Journal Article] Supramolecular Chirogenesis in Weakly Interacting Hosts: Role of the Temperature, Structural and Electronic Factors in Enhancement of Chiroptical Sensitivity. (2008)
  • Author(s): V. Borovkov, T. Yamamoto, H. Higuchi,Y. Inoue
  • Journal Title: Org. Lett. 10 Pages: 1283-1286
  • Peer Reviewed
• [Journal Article] The Octaethylporphyrin-Dihexylbithiophe ne Derivatives Combined with Pyridine and Pyrimidine Rings. Their Syntheses and Proton-Mediated and Heat-Driven Spectral Changes (2008)
  • Author(s): H. Higuchi, N. Hayashi, T.Matsukihira, T.Kawakami, T. Takizawa, J. Saito, K.Miyabayashi, M. Miyake
  • Journal Title: Heterocycles 76 Pages: 353-380
  • Peer Reviewed
• [Journal Article] 4, 4'-Dichloro-2, 2'-(piperazine-1, 4-diyldimethylene)diphenol. (2008)
  • Author(s): Koji Kubono
  • Journal Title: Acta Crystallographica E64 Pages: 2446-2446
  • Peer Reviewed
• [Journal Article] The Octaethylporphyrin-Dihexylbithiophene Derivatives Combined withPyridine and Pyrimidine Rings. Their Syntheses and Proton-Mediated andHeat-Driven Spectral Changes (2008)
  • Author(s): Hiroyuki Higuchi
  • Journal Title: Heterocycles 76 Pages: 353-380
  • Peer Reviewed
• [Journal Article] Intramolecular Singlet and TripletExcimers of Triply Bridged[3.3.n](3,6,9)Carbazolophanes. (2007)
  • Author(s): H. Benten, J. Guo, H. Ohkita, *S. Ito,M. Yamamoto, N. Sakumoto, K. Hori, Y.Tohda, and K. Tani
  • Journal Title: J. Phys. Chem. B 111 Pages: 10905-10914
  • Peer Reviewed
• [Journal Article] Synthesis and Properties of Partially Overlapped [3.n](3,9)Carbazolophanes (2007)
  • Author(s): K. Tani, S. Yamamoto, K. Kubono,K.Hori, Y. Tohda, H. Takemura, Y.Nakamura, J. Nishimura, H. Benten, H.Ohkita, S. Ito, and M.Yamamoto
  • Journal Title: 36 Pages: 460-461
  • NAID: 10018830157
  • Peer Reviewed
• [Journal Article] Synthesis and Properties of Partially Overlapped [3.n](3,9)Carbazolophanes (2007)
  • Author(s): Keita Tani
  • Journal Title: Chemistry Letters 36 Pages: 460-461
  • NAID: 10018830157
  • Peer Reviewed
• [Journal Article] Intramolecular Singlet and Triplet Excimers of Triply Bridged [3.3.n](3,6,9)-Carbazolonhanes (2007)
  • Author(s): Hiroaki Benten
  • Journal Title: The Journal of Physical Chemistry B 111 Pages: 10905-10914
  • Peer Reviewed
• [Journal Article] Orientation and Substituent Effects on the Properties of the Diacetylene-group Connected Octaethylporphyrin-dihexylbithiophene Derivatives(OEP-DHBTh-X)Carrying Electron-withdrawing Groups (2007)
  • Author(s): N. Hayashi
  • Journal Title: Bull. Chem. Soc. Jpn. 80 Pages: 371-386
  • Peer Reviewed
• [Journal Article] Synthesis and Electronic Properties of Dimeric Octaethylporphyin(OEP)Derivatives Spaced with ρ-Phenylene Group [OEP-(p-Phen)n-OEP]. A Comparative Study with Dihexylbithiophene(DHBTh)Group-Spaced OEP Dimers [OEP-(DHBTh)n-OEP] (2007)
  • Author(s): N.Hayashi
  • Journal Title: Sci. Tec. Adv. Mat. 8 Pages: 296-305
  • Peer Reviewed
• [Journal Article] Synthesis, Structure, and Properties of Benzoquinone Dimer and Trimers Bearing t-Bu Substituents (2007)
  • Author(s): N.Hayashi
  • Journal Title: Org. Lett. 9 Pages: 5417-5420
  • Peer Reviewed
• [Presentation] カルバゾールアミン体とハロゲン化アシル類との反応 (2009)
  • Author(s): 今福理沙・堀 一繁・任田康夫・辨天宏明・大北英生・伊藤紳三郎・山本雅英・谷 敬太
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 千葉
  • Year and Date: 2009-03-27
• [Presentation] ペリレンジイミドを有するカルバゾール誘導体の合成と性質 (2009)
  • Author(s): 木村雄一郎・谷敬太・堀一繁・ 任田康夫・辨天宏明・大北英生・伊藤紳三郎・山本雅英
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 千葉
  • Year and Date: 2009-03-27
• [Presentation] 機能を有するカルバゾール(カルバゾロファン)の合成と性質 (2008)
  • Author(s): 谷 敬太
  • Organizer: 第2回有機π電子系シンポジウム
  • Place of Presentation: 広島
  • Year and Date: 2008-12-06
• [Presentation] カルバゾールあるいはカルバゾロファンアミン体とベンジルブロミド誘導体との反応 (2008)
  • Author(s): 今福理沙・堀 一繁・任田康夫・谷 敬太
  • Organizer: 第2回有機π電子系シンポジウム
  • Place of Presentation: 広島
  • Year and Date: 2008-12-05
• [Presentation] カルバゾロファン-ペリレンジイミド連結系の合成と性質 (2008)
  • Author(s): 木村雄一郎・谷敬太・堀一繁・ 任田康夫・郭嘉謨・辨天宏明・大北英生・伊藤紳三郎・山本雅英
  • Organizer: 第2回π電子系シンポジウム
  • Place of Presentation: 広島
  • Year and Date: 2008-12-05
• [Presentation] カルバゾール発色団を有するジアリールエテン誘導体のフォトクロミック特性と電導性スイッチング (2008)
  • Author(s): 増崎皓哉・庄司健太郎・堀 一繁・任田 康夫・山本宗幸・辻岡 強・谷 敬太
  • Organizer: 第2回π電子系シンポジウム
  • Place of Presentation: 広島
  • Year and Date: 2008-12-05
• [Presentation] [3.3](3,9)カルバゾロファン-尿素誘導体の合成と性質 (2008)
  • Author(s): 嶽佑輔・谷敬太・堀一繁・任田康夫・久保埜公二・郭嘉謨・辨天宏明・大北英生・伊藤紳三郎・山本雅英
  • Organizer: 第19回基礎有機化学討論会
  • Place of Presentation: 大阪
  • Year and Date: 2008-10-05
• [Presentation] カルバゾールアミン体と臭化ベンジル誘導体との反応 (2008)
  • Author(s): 今福理沙・堀 一繁・任田康夫・郭 嘉謨・辨天宏明・大北英生・伊藤紳三郎・山本雅英・谷 敬太
  • Organizer: 第19回基礎有機化学討論会
  • Place of Presentation: 大阪
  • Year and Date: 2008-10-05
• [Presentation] カルバゾロファン-ペリレンジイミド-カルバゾロファン連結分子の合成と性質 (2008)
  • Author(s): 木村雄一郎・谷敬太・堀一繁・任田康夫・郭嘉謨・辨天宏明・大北英生・伊藤紳三郎・山本雅英
  • Organizer: 第19回基礎有機化学討論
  • Place of Presentation: 大阪
  • Year and Date: 2008-10-05
• [Presentation] NOVEL FLUOROIONOPHORES, [m.5](3,9)-CARBAZOLOPHANES, FOR THE DETECTION OF METAL ION. (2008)
  • Author(s): Keita Tani, Shinya Yamamoto, Ryota Murakami, Koji Kubono, Kazushige Hori,Yasuo Tohda, Hiroaki Benten,Hideo Ohkita,Shinzaburo Ito, and Masahide Yamamoto
  • Organizer: XXII IUPAC Symposium on Photochemistry (ICP2008)
  • Place of Presentation: Gothenburg (Sweden)
  • Year and Date: 2008-07-29
• [Presentation] NOVEL FLUOROIONOPHORES, [m. 5](3, 9)CARBAZOLOPHANES, FOR THEDETECTION OF METAL ION (2008)
  • Author(s): Keita Tani
  • Organizer: XXII IUPAC Symposium on Photochemistry
  • Place of Presentation: Gothenburg
  • Year and Date: 2008-07-29
• [Presentation] Synthesis and Properties of [3.3.n](3,6,9)- Carbazolophanes. (2008)
  • Author(s): Keita Tani, Koji Kubono, Kazushige Hori, Yasuo Tohda, Hiroaki Benten,Jiamo Guo, Hideo Ohkita, and Shizaburo Ito, Masahide Yamamoto
  • Organizer: ISNA-12
  • Place of Presentation: Hyogo
  • Year and Date: 2008-07-23
• [Presentation] 二架橋系カルバゾロファンの合成と性質 (2008)
  • Author(s): 青木慎治・谷 敬太・堀 一繁・任田康夫・郭 嘉謨・辨天宏明・大北英生・伊藤紳三郎・山本 雅英
  • Organizer: 第88回日本化学会春季年会
  • Place of Presentation: 東京
  • Year and Date: 2008-03-27
• [Presentation] 溶媒極性に応答するジオキサ[3.3](3,6)カルバゾロファンの分子内エキシマー生成 (2008)
  • Author(s): 山中翔・久田研次・堀 照夫・谷 敬太
  • Organizer: 第87回日本化学会春季年会
  • Place of Presentation: 東京
  • Year and Date: 2008-03-27
• [Presentation] カルバゾロファン-ペリレンジイミド連結系の合成と性質 (2007)
  • Author(s): 青木慎治・谷敬太・堀一繁・任田康夫
  • Organizer: 第1回π電子系シンポジウム
  • Place of Presentation: 東京
  • Year and Date: 2007-12-07
• [Presentation] イミノ基を有するカルバゾロファンの合成と金属イオン存在下での発光挙動 (2007)
  • Author(s): 谷 敬太・梶 敬一・中川小百合・久保埜公二・堀 一繁・任田康夫・辨天宏明・大北英生・伊藤紳三郎・山本雅英
  • Organizer: 構造有機化学討論会
  • Place of Presentation: 北海道
  • Year and Date: 2007-10-27
• [Presentation] 酸素架橋型[3.5](3,9)カルバゾロファンのブロモおよびフェニル体の合成と性質 (2007)
  • Author(s): 嶽佑輔・谷敬太・堀一繁・任田康夫・郭嘉謨・辨天宏明・大北英生・伊藤紳三郎・山本雅英
  • Organizer: 第37回構造有機化学討論会
  • Place of Presentation: 北海道
  • Year and Date: 2007-10-27
• [Presentation] フェニル基を有する部分重なり型[3.3](3,9)カルバゾロファン-テレフタレート連結系の合成と性質 (2007)
  • Author(s): 青木慎治・谷敬太・堀一繁・任田康夫・郭嘉謨・辨天宏明・大北英生・伊藤紳三郎・山本雅英
  • Organizer: 第37回構造有機化学討論会
  • Place of Presentation: 北海道
  • Year and Date: 2007-10-27
• [Presentation] Synthesis and Properties of [3.3](3,9)Carbazolophane-Acceptor Dyads. (2007)
  • Author(s): Keita Tani, Kunihiko Sako, Kazushige Hori,Yasuo Tohda, Hiroaki Benten, Jiamo Guo,Hideo Ohkita, Shizaburo Ito, and Masahide Yamamoto
  • Organizer: XXI IUPAC Symposium on Photochemistry (ICP2007)
  • Place of Presentation: Cologne (Germany)
  • Year and Date: 2007-08-02
• [Presentation] Synthesis and Photophysical Properties of Carbazole-Benzoquinone System. (2007)
  • Author(s): Shinji Aoki, Keita Tani, Kazushige Hori,Yasuo Tohda, Hiroaki Benten, Jiamo Guo,Hideo Ohkita,Shinzaburo Ito, and Masahide Yamamoto
  • Organizer: XXI IUPAC Symposium on Photochemistry (ICP2007)
  • Place of Presentation: Cologne (Germany)
  • Year and Date: 2007-08-02
• [Presentation] Intramolecular Singlet and Triplet Excimers of Fuliy-Overlapped Carbazolophanes. (2007)
  • Author(s): Hiroaki Benten, Jiamo Guo, Hideo Ohkita,Shizaburo Ito, and Masahide Yamamoto, and Keita Tani
  • Organizer: XXI IUPAC Symposium on Photochemistry(ICP2007)
  • Place of Presentation: Cologne (Germany)
  • Year and Date: 2007-07-31
• [Presentation] Synthesis and Properties of [3.3.n](3,6,9)Carbazolophanes. (2007)
  • Author(s): Keita Tani
  • Organizer: ISNA-12
  • Place of Presentation: Awaji Yumebutai Inter-national Conference Center
  • Year and Date: 2007-07-23
• [Presentation] 重なり型カルバゾロファンとペリレンジイミドを有するDD-A-DD 連結系の合成と性質 (2007)
  • Author(s): 青木慎治・谷敬太・堀一繁・任田康夫・郭嘉謨・辨天宏明・大北英生・伊藤紳三郎・山本雅英
  • Organizer: 2007年光化学討論会
  • Place of Presentation: 長野
• [Remarks] 大阪教育大学リポジトリ
  • URL: http://ir.lib.osaka-kyoiku.ac.jp/dspace/