β-to-β 2,5-Pyrrolylene-Linked Cyclic Porphyrin Oligomers

Yutao Rao; Jun Oh Kim; Woojae Kim; Guangming Zhong; Bangshao Yin; Mingbo Zhou; Hiroshi Shinokubo; Naoki Aratani; Takayuki Tanaka; Shubin Liu; Atsuhiro Osuka; Dongho Kim; Jianxin Song

doi:10.1002/chem.201601306

β-to-β 2,5-Pyrrolylene-Linked Cyclic Porphyrin Oligomers

Chemistry. 2016 Jun 20;22(26):8801-4. doi: 10.1002/chem.201601306. Epub 2016 May 17.

Authors

Yutao Rao¹, Jun Oh Kim², Woojae Kim², Guangming Zhong¹, Bangshao Yin¹, Mingbo Zhou¹, Hiroshi Shinokubo³, Naoki Aratani⁴, Takayuki Tanaka⁵, Shubin Liu⁶, Atsuhiro Osuka⁷, Dongho Kim⁸, Jianxin Song⁹

Affiliations

¹ Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Key Laboratory of Application and Assembly of Organic Functional Molecules, Hunan Normal University, Changsha, 410081, China.
² Spectroscopy Laboratory for Functional π-Electronic Systems and Department of Chemistry, Yonsei University, Seoul, 03722, Korea.
³ Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Nagoya, 464-8603, Japan.
⁴ Nara Institute of Science and Technology, Japan.
⁵ Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502, Japan.
⁶ Division of Research Computing, Information Technology Services, University of North Carolina, Chapel Hill, North Carolina, 27599, USA.
⁷ Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502, Japan. osuka@kuchem.kyoto-u.ac.jp.
⁸ Spectroscopy Laboratory for Functional π-Electronic Systems and Department of Chemistry, Yonsei University, Seoul, 03722, Korea. dongho@yonsei.ac.kr.
⁹ Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Key Laboratory of Application and Assembly of Organic Functional Molecules, Hunan Normal University, Changsha, 410081, China. jxsong@hunnu.edu.cn.

PMID: 27124728
DOI: 10.1002/chem.201601306

Abstract

β-to-β 2,5-Pyrrolylene linked cyclic porphyrin oligomers have been synthesized by Suzuki-Miyaura coupling of 2,5-diborylpyrrole and 3,7-dibromoporphyrin. The cyclic porphyrin oligomers exhibit roughly coplanar structures, strong excitonic coupling, small electrochemical HOMO-LUMO gaps, and ultrafast excitation energy transfer between the neighboring porphyrins via the pyrrolylene bridge.

Keywords: excitation energy transfer; exciton coupling; nickel; porphyrinoids; porphyrins.