Exploitation of synthetic methods for highly conjugated compounds and evaluation of their properties

2013 Fiscal Year Final Research Report

• Project/Area Number: 23350020
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Ehime University
• Principal Investigator: UNO Hidemitsu 愛媛大学, 理工学研究科, 教授 (20168735)
• Co-Investigator(Kenkyū-buntansha): MORI Shigeki 愛媛大学, 総合科学研究支援センター, 助教 (30572028) ; OKUJIMA Tetsuo 愛媛大学, 大学院・理工学研究科, 准教授 (60359924)
• Co-Investigator(Renkei-kenkyūsha): YAMADA Hiroko 奈良先端科学技術大学院, 物質創成科学研究科, 教授 (20372724) ; KOBAYASHI Nagao 東北大学, 東北大学, 教授 (60124575)
• Project Period (FY): 2011-04-01 – 2014-03-31
• Keywords: 構造有機化学 / 有機電子材料 / 高共役化合物

Research Abstract

We investigated synthesis of pi-system-fused porphyrin oligomers, bisthiaporphyrin, cyclo[n]pyrroles, picenes, [5]helicenes, bisBODIPYs, and naphth[2,3-f]isoindoles mainly based on the pericyclic cycloreversion as the key step and analyzed their electronic properties. The two-photon absorption property of pi-system-fused porphyrin oligomers is proven to be affected not by the numbers but mostly by the shapes of their pi systems. Stable bisBODIPYs bearing strong absorptions only in the NIR region have been explored.

Research Products

• [Journal Article] Face- and regio-selectivity in electrophilic phenylsulfenylation of 7-tert-butoxybicyclo- [2.2.1]hepta-2,5-dienes (2014)
  • Author(s): H. Uno, M. Yoshino, A. Seike, S. Mori, T. Nakae, and T. Okujima
  • Journal Title: Heteroatom Chem Volume: (in press)
  • DOI: 10.1002/hc.21172
• [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, and H. Uno
  • Journal Title: Chem. Lett Volume: 43 Pages: 504-506
• [Journal Article] Yellow NIR dye : π-fused bisbenzo- BODIPYs 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, and H. Uno
  • Journal Title: Org. Biomol. Chem Volume: 12 Pages: 1309-1317
• [Journal Article] Study on Hinsberg thiophene synthesis of 4,8-dihydro-4,8-ethanobenzo[1,2-c;4,5-c']dithiop hene (2014)
  • Author(s): K. Tagawa, S. Mori, T. Nakae, T. Okujima, and H. Uno
  • Journal Title: Heterocycles Volume: 88 Pages: 453-462
• [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, H. Yamada, and H. Uno
  • Journal Title: Heterocycles Volume: 88 Pages: 417-424
• [Journal Article] MCD spectroscopy and TD-DFT calculations of low-symmetry acenaphthoporphyrins with dual fluorescence (2013)
  • Author(s): J. Mack, J. Nakamura, T. Okujima, H. Yamada, H. Uno, N. Kobayashi, J
  • Journal Title: Porphyrins Phthalocyanines Volume: 17 Pages: 996-1007
• [Journal Article] Acenaphthylene-Fused Cyclo[8]pyrroles with Intense Near-IR-Region Absorption Bands (2013)
  • Author(s): T. Okujima, C. Ando, J. Mack, S. Mori, I. Hisaki, T. Nakae, H. Yamada, K. Ohara, N. Kobayashi, H. Uno
  • Journal Title: Chem. Eur. J Volume: 19 Pages: 13970-13978
• [Journal Article] Shape-Dependent Two-Photon Absorption in Two-Dimensionally Extended Benzoporphyrin Arrays (2013)
  • Author(s): P. Kim, S. Ham, J. Oh, H. Uoyama, H. Watanabe, K. Tagawa, H. Uno and D. Kim
  • Journal Title: Phys. Chem. Chem. Phys Volume: 10612-10615 Pages: 15
• [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 and H. Uno
  • Journal Title: RSC Adv Volume: 3006-3016 Pages: 3
• [Journal Article] Synthesis and properties of azulenesubstituted thiophenes, terthiophenes and dithienothiophenes (2012)
  • Author(s): T. Okujima, A. Toda, Y. Miyashita, A. Nonoshita, H. Yamada, N. Ono, and H. Uno
  • Journal Title: Heterocycles Volume: 637-648 Pages: 86
• [Journal Article] Synthesis of bis-naphthoporphyrins (2012)
  • Author(s): H. Uoyama, H. Yamada, T. Okujima, and H. Uno
  • Journal Title: Heterocycles Volume: 86 Pages: 515-534
• [Journal Article] Retro-Diels-Alder Approach to the Synthesis of π-Expanded Azuliporphyrins and Their Porphyrinoid Aromaticity (2012)
  • Author(s): T. Okujima, T. Kikkawa, H. Nakano, H. Kubota, N. Fukugami, N. Ono, H. Yamada, H. Uno
  • Journal Title: Chem. Eur. J Volume: 18 Pages: 12854-12863
• [Journal Article] π-Fused bis-BODIPY as a candidate for NIR dyes (2012)
  • Author(s): M. Nakamura, H. Tahara, K. Takahashi, T. Nagata, H. Uoyama, D. Kuzuhara, S. Mori, T. Okujima, H. Yamada, and H. Uno
  • Journal Title: Org. Biomol. Chem. Volume: 10 Pages: 6840-6849
• [Journal Article] Effective synthesis of diiodinated picene and dibenzo[a,h]anthracene by AuCl- catalyzed double cyclization (2012)
  • Author(s): T. Nakae, R. Ohnishi, Y. Kitahata, T. Soukawa, H. Sato, S. Mori, T. Okujima, H. Uno, and H. Sakaguchi
  • Journal Title: Tetrahedron Lett Volume: 53 Pages: 1617-1619
• [Journal Article] Fasile Synthesis of 4,9-Dihydro-2H-benz[f]- and 4,11-Dihydro-2H-naphth[2,3-f]isoin- doles and Their Utility for Porphyrin Synthesis (2012)
  • Author(s): C. Cai, H. Uoyama, M. Nakamura, and H. Uno
  • Journal Title: Heterocycles Volume: 84 Pages: 829-841
• [Journal Article] Porphyrin Molecular Tweezers for Fullerenes (2011)
  • Author(s): H. Uno, M. Furukawa, A. Fujimoto, H. Uoyama, H. Watanabe, T. Okujima, H. Yamada, S. Mori, M. Kuramoto, T. Iwamura, N. Hatae, F. Tani, and N. Komatsu, J
  • Journal Title: Porphyrins Phthalocyanines Volume: 15 Pages: 951-963
• [Journal Article] Tetrabenzodiazaporphyrin : the semiconducting hybrid of phthalocyanine and tetrabenzoporphyrin (2011)
  • Author(s): T. Okujima, G. Jin, S. Otsubo, S. Aramaki, N. Ono, H. Yamada, and H. Uno
  • Journal Title: J. Porphyrins Phthalocyanines Volume: 15 Pages: 697-703
• [Journal Article] Cyclo[8]isoindoles : Ring-Expanded and Annelated Porphyrinoids (2011)
  • Author(s): T. Okujima, G. Jin, N. Matsumoto, J. Mack, S. Mori, K. Ohara, D. Kuzuhara, C. Ando, N. Ono, H. Yamada, H. Uno, and N. Kobayashi
  • Journal Title: Angew. Chem. Int. Ed Volume: 50 Pages: 5699-5703
• [Journal Article] Synthesis of π-Expanded O-Chelated Boron-Dipyrromethene As an NIR Dye (2011)
  • Author(s): Y. Tomimori, T. Okujima, T. Yano, S. Mori, N. Ono, H. Yamada, and H. Uno
  • Journal Title: Tetrahedron Volume: 67 Pages: 3187-3193
• [Presentation] Selective porphyrin molecular tweezers for C60 and C70 (2012)
  • Author(s): H. Uno, H. Watanabe, K. Tagawa, S. Mori, T. Okujima, and N. Komatsu
  • Organizer: 7th International Conference on Porphyrins and Phthalocyanines (ICPP-7)
  • Place of Presentation: Jeju, Korea
  • Year and Date: 2012-07-26
  • Invited
• [Presentation] Efficient synthesis of highly π-expanded heterocycles based on the pericyclic cycloreversion (2011)
  • Author(s): H. Uno
  • Organizer: 23rd International Congress of Heterocyclic Chemistry
  • Place of Presentation: Glasgow, UK
  • Year and Date: 2011-08-01
  • Invited
• [Book] 有機スペクトル解析-IR, NMR, MS データを読む (2014)
  • Author(s): 臼杵克之介, 宇野英満, 築部浩編
  • Total Pages: 1-143
  • Publisher: 丸善
• [Book] Methods and Applications of Cycloaddition Reactions in Organic Syntheses (2014)
  • Author(s): Nagatoshi Nishiwaki ed
  • Total Pages: 429-470
  • Publisher: John Wiley & Sons Inc
• [Book] 高次π 空間の創発と機能開発 (2012)
  • Author(s): 赤坂健, 大須賀篤弘, 福住俊一, 神取秀樹, 監修
  • Total Pages: 73-79
  • Publisher: シーエムシー出版
• [Remarks]
  • URL: http://chem.sci.ehime-u.ac.jp/~orgchem1/
• [Patent(Industrial Property Rights)] ビス-ボロンジメテン系色素 (2013)
  • Inventor(s): 宇野英満, 北束政 波,増田豪, 青木正矩
  • Industrial Property Rights Holder: 愛媛大学, (株)日本触媒
  • Industrial Property Rights Type: 特許
  • Industrial Property Number: 特願2013-170675
  • Filing Date: 2013-08-20
• [Patent(Industrial Property Rights)] ボラジアジン系色素 (2013)
  • Inventor(s): 宇野英満, 芳野真己, 増田豪, 青木正矩
  • Industrial Property Rights Holder: 愛媛大学,(株)日本触媒
  • Industrial Property Rights Type: 特許
  • Industrial Property Number: 特願2013-170676
  • Filing Date: 2013-08-20
• [Patent(Industrial Property Rights)] イソインドール類およびそのポリマー (2013)
  • Inventor(s): 宇野英満, 増田豪
  • Industrial Property Rights Holder: 愛媛大学, (株)日本触媒
  • Industrial Property Rights Type: 特許
  • Industrial Property Number: 特願2013-78992,特開2013-129682
  • Filing Date: 2013-04-04
• [Patent(Industrial Property Rights)] イソインドール類およびそのポリマー (2013)
  • Inventor(s): 宇野英満, 増田豪
  • Industrial Property Rights Holder: 愛媛大学, (株)日本触媒
  • Industrial Property Rights Type: 特許
  • Industrial Property Number: 5294374
  • Acquisition Date: 2013-06-21
• [Patent(Industrial Property Rights)] ビス-ボロンジメテン系色素及びその前駆体 (2012)
  • Inventor(s): 宇野英満, 中村光則, 高橋功太郎
  • Industrial Property Rights Holder: 愛媛大学, (株)日本触媒
  • Industrial Property Rights Type: 特許
  • Industrial Property Number: 特願2012-27806,特開2013-177551
  • Filing Date: 2012-02-10
• [Patent(Industrial Property Rights)] 新規化合物 (2011)
  • Inventor(s): 大橋幸恵, 杉山直樹, 宇野英満, 奥島鉄雄, 松本直樹
  • Industrial Property Rights Holder: 愛媛大学, (株)JSR
  • Industrial Property Rights Type: 特許
  • Industrial Property Number: 特願2011-194015,特開2013-53120
  • Filing Date: 2011-09-06