Development of Hugely Conjugated Carbazole-Containing Porphyrinoids

• Project/Area Number: 23750231
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Organic industrial materials
• Research Institution: Okayama University (2013); Keio University (2011-2012)
• Principal Investigator: MAEDA Chihiro 岡山大学, 自然科学研究科, 助教 (80581371)
• Project Period (FY): 2011 – 2012
• Project Status: Completed (Fiscal Year 2013)
• Budget Amount: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000); Fiscal Year 2012: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2011: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
• Keywords: 機能性有機材料 / ポルフィリノイド / 国際情報交換 / 国際情報交流

Research Abstract

Novel fused porphyrinoids based on carbazole frameworks have been developed. Oligothiophene- or selenophene-bridged carbazole dimers have been synthesized, and substituent effects of ethnyl groups on the macrocycles have been investigated. These porphyrinoids exhibit strong NIR absorption. It was found that introduction of substituents control the NIR absorption.

Research Products

• [Journal Article] Synthesis of carbazole-based hetero-core-modified porphyrins (2014)
  • Author(s): C. Maeda、M. Masuda、N. Yoshioka
  • Journal Title: Org. Biomol. Chem Volume: 12巻 Issue: 17 Pages: 2656-2662
  • DOI: 10.1039/c3ob42564a
  • Peer Reviewed
• [Journal Article] Effective π‐Extension of Carbazole-Based Thiaporphyrins by Peripheral Phenylethynyl Substituents (2013)
  • Author(s): C. Maeda, M. Masuda, N. Yoshioka
  • Journal Title: Org. Lett. Volume: 15 Issue: 14 Pages: 3566-3569
  • DOI: 10.1021/ol401403n
  • Peer Reviewed
• [Journal Article] Synthesis of Carbazole-Based Selenaporphyrin via Annulation (2013)
  • Author(s): M. Masuda、C. Maeda、N. Yoshioka
  • Journal Title: Org. Lett Volume: 15巻 Issue: 3 Pages: 578-581
  • DOI: 10.1021/ol303392g
  • Peer Reviewed
• [Journal Article] Synthesis and Characterization of Carbazole-Based Expanded Thiaporphyrins (2013)
  • Author(s): M. Masuda、C. Maeda
  • Journal Title: Chem. Eur. J Volume: 19巻 Issue: 9 Pages: 2971-2975
  • DOI: 10.1002/chem.201202573
  • Peer Reviewed
• [Journal Article] Peripherally ethynylated carbazole-based core-modified porphyrins (2012)
  • Author(s): C. Maeda、N. Yoshioka
  • Journal Title: Org. Biomol. Chem Volume: 10巻 Issue: 27 Pages: 5182-5185
  • DOI: 10.1039/c2ob25645b
  • Peer Reviewed
• [Journal Article] Synthesis and Characterization of Novel Fused Porphyrinoids Based on Cyclic Carbazole[2]indolones (2012)
  • Author(s): C. Maeda、N. Yoshioka
  • Journal Title: Org. Lett Volume: 14巻 Issue: 8 Pages: 2122-2125
  • DOI: 10.1021/ol300585v
  • Peer Reviewed
• [Journal Article] Molecular engineering and solvent dependence of excitation energy hopping in self-assembled porphyrin boxes (2012)
  • Author(s): H. W. Bahng, P. Kim, Y. M. Sung, C. Maeda, A. Osuka, and D. Kim
  • Journal Title: Chem. Commun. Volume: 48 Issue: 35 Pages: 4181-4183
  • DOI: 10.1039/c2cc30834g
  • Peer Reviewed
• [Journal Article] Synthesis of Carbazole-Containing Porphyrinoids by a Multiple Annulation Strategy : A Core-Modified and π-Expanded Porphyrin (2011)
  • Author(s): Maeda, C., Yoneda, T., Aratani, N., Yoon, M-C., Lim, J.M., Kim, D., Yoshioka, N., Osuka, A.
  • Journal Title: Angew.Chem., Int.Ed. Volume: 50 Issue: 25 Pages: 5691-5694
  • DOI: 10.1002/anie.201101864
  • Peer Reviewed
• [Journal Article] New Synthetic Strategy for Diporphyrins : Pinacol Coupling-Rearrangement (2011)
  • Author(s): S.Tokuji, C.Maeda, H.Yorimitsu, A.Osuka
  • Journal Title: Chem.Eur.J. Volume: 17 Issue: 26 Pages: 7154-7157
  • DOI: 10.1002/chem.201100872
  • Peer Reviewed
• [Presentation] エチニル基を導入した含カルバゾールポルフィリンの合成 (2013)
  • Author(s): 前田千尋
  • Organizer: 第30回有機合成化学セミナー
  • Place of Presentation: 倉敷
  • Year and Date: 2013-09-18
• [Presentation] Synthesis of Carbazole -Based Porphyrinoids (2013)
  • Author(s): Chihiro Maeda
  • Organizer: Collaborative Conf erence on 3D & Materials Research 2013
  • Place of Presentation: Cheju, Korea
  • Year and Date: 2013-06-24
• [Presentation] カルバゾール骨格を有する核置換ポルフィリノイドの合成と性質 (2013)
  • Author(s): 前田千尋・増田幹・吉岡直樹
  • Organizer: 日本化学会第93春年会
  • Place of Presentation: 草津
  • Year and Date: 2013-03-24
• [Presentation] Synthesis and Property of Carbazole-Containing Porphy rins (2013)
  • Author(s): C. Maeda, N. Yoshioka
  • Organizer: Third International Conference on Multifunctional, Hybrid and Nanomateria ls
  • Place of Presentation: Sorrento, Italy
  • Year and Date: 2013-03-03
• [Presentation] カルバゾールとインドール骨格を有するポルフィリノイドの合成と性質 (2013)
  • Author(s): 前田千尋、吉岡直樹
  • Organizer: 日本化学会第92春年会
  • Place of Presentation: 横浜
  • Year and Date: 2013-02-26
• [Presentation] Synthesis of Carbazole-Based Porphyrinoids (2013)
  • Author(s): Chihiro Maeda
  • Organizer: Collaborative Conference on 3D & Materials Research 2013
  • Place of Presentation: Cheju, Korea
  • Invited
• [Presentation] カルバゾール有するチアポルフィリン及びオキサポルフィリンの合成と性質 (2012)
  • Author(s): 前田千尋・増田幹・吉岡直樹
  • Organizer: 第23回基礎有機化学討論会
  • Place of Presentation: 京都
  • Year and Date: 2012-09-20
• [Presentation] Carbazole-containing Porphyrin (2012)
  • Author(s): C. Maeda, N. Yoshioka
  • Organizer: Seventh International Conference on Porphyrins and Phthalocyanines
  • Place of Presentation: Cheju, Korea
  • Year and Date: 2012-07-03
• [Presentation] カルバゾールを部分骨格とする環拡張チアポルフィリンの合成と性質 (2012)
  • Author(s): 増田幹、前田千尋、吉岡直樹
  • Organizer: 日本化学会第92春年会
  • Place of Presentation: 横浜
  • Year and Date: 2012-03-26
• [Presentation] カルバゾールとインドール骨格を有するポルフィリノイドの合成と性質 (2012)
  • Author(s): 前田千尋、吉岡直樹
  • Organizer: 日本化学会第92春年会
  • Place of Presentation: 慶應義塾大学
• [Presentation] カルバゾールを部分骨格とする環拡張チアポルフィリンの合成と性質 (2012)
  • Author(s): 増田幹、前田千尋、吉岡直樹
  • Organizer: 日本化学会第92春年会
  • Place of Presentation: 慶應義塾大学
• [Presentation] 環化反応を用いた六重ベンゾ縮環ルビリンの合成 (2011)
  • Author(s): 益田美加子、前田千尋、吉岡直樹
  • Organizer: 第22回基礎有機化学討論会
  • Place of Presentation: つくば
  • Year and Date: 2011-09-22
• [Presentation] カルバゾールとチオフェンから形成される環拡張ポルフィリンの合成と性質 (2011)
  • Author(s): 増田幹、前田千尋、吉岡直樹
  • Organizer: 第22回基礎有機化学討論会
  • Place of Presentation: つくば
  • Year and Date: 2011-09-21
• [Presentation] カルバゾールとインドール骨格を有するポルフィリノイドの合成と性質 (2011)
  • Author(s): 前田千尋、吉岡直樹
  • Organizer: 第22回基礎有機化学討論会
  • Place of Presentation: つくば
  • Year and Date: 2011-09-21
• [Presentation] Synthesis of Carbazole-Incorporated Porphyrinoids (2011)
  • Author(s): C. Maeda, N. Yoshioka
  • Organizer: 14th International Symposium on Novel Aromatic Compounds
  • Place of Presentation: Eugene, USA
  • Year and Date: 2011-07-15
• [Presentation] Synthesis of Carbazole-Incorporated Porphyrinoids (2011)
  • Author(s): Chihiro Maeda, Naoki Yoshioka
  • Organizer: ISNA-14
  • Place of Presentation: Eugene, USA
• [Presentation] カルバゾールとインドール骨格を有するポルフィリノイドの合成と性質 (2011)
  • Author(s): 前田千尋、吉岡直樹
  • Organizer: 第22回基礎有機化学討論会
  • Place of Presentation: つくば国際会議場
• [Presentation] カルバゾールとチオフェンから形成される環拡張ポルフィリンの合成と性質 (2011)
  • Author(s): 増田幹、前田千尋、吉岡直樹
  • Organizer: 第22回基礎有機化学討論会
  • Place of Presentation: つくば国際会議場
• [Presentation] 環化反応を用いた六重ベンゾ縮環ルビリンの合成 (2011)
  • Author(s): 益田美加子、前田千尋、吉岡直樹
  • Organizer: 第22回基礎有機化学討論会
  • Place of Presentation: つくば国際会議場
• [Presentation] カルバゾール有するチアポルフィリン及びオキサポルフィリンの合成と性質
  • Author(s): 前田千尋・増田幹・吉岡直樹
  • Organizer: 第23回基礎有機化学討論会
  • Place of Presentation: 京都テルサ
• [Presentation] カルバゾール骨格を有する核置換ポルフィリノイドの合成と性質
  • Author(s): 前田千尋・増田幹・吉岡直樹
  • Organizer: 日本化学会第93春年会
  • Place of Presentation: 立命館大学
• [Presentation] Carbazole-containing Porphyrin
  • Author(s): C. Maeda, N. Yoshioka
  • Organizer: Seventh International Conference on Porphyrins and Phthalocyanines
  • Place of Presentation: Cheju
• [Presentation] Synthesis and Property of Carbazole-Containing Porphyrins
  • Author(s): C. Maeda, N. Yoshioka
  • Organizer: Third International Conference on Multifunctional, Hybrid and Nanomaterials
  • Place of Presentation: Sorrento