5-Thiaporphyrinium cation: effect of sulphur incorporation on excited state dynamics

Asahi Takiguchi; Naoto Inai; Seongsoo Kang; Masaya Hagai; Seokwon Lee; Takeshi Yanai; Dongho Kim; Hiroshi Shinokubo

doi:10.1039/D2CC00522K

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5-Thiaporphyrinium cation: effect of sulphur incorporation on excited state dynamics†

Asahi Takiguchi,

^a Naoto Inai,

^b Seongsoo Kang,^c Masaya Hagai,

^d Seokwon Lee,^c Takeshi Yanai,

*^be Dongho Kim

*^c and Hiroshi Shinokubo

*^a

Author affiliations

* Corresponding authors

^a Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya, Aichi 464-8603, Japan
E-mail: hshino@chembio.nagoya-u.ac.jp

^b Department of Chemistry, Graduate School of Science, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8602, Japan
E-mail: yanait@chem.nagoya-u.ac.jp

^c Department of Chemistry, Spectroscopy Laboratory for Functional π-Electronic Systems Yonsei University, Seoul 03722, South Korea
E-mail: dongho@yonsei.ac.kr

^d Department of Chemistry, School of Science, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8602, Japan

^e Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8602, Japan

Abstract

We synthesised thionium-ion embedded aromatic porphyrinoids: a free-base 5-thiaporphyrinium cation and its zinc complex. The sulphur atom effectively participates in the macrocyclic π-conjugation. Fluorescence quantum yields of thiaporphyrinium cations were lower than 1% unlike oxaporphyrinium cations. Detailed photophysical analysis and DFT calculations clarified the vibrational mode regarding the out-of-plane motion of the sulphur atom induced ultrafast quenching of the excited state in comparison to the corresponding oxaporphyrinium cations.

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DOI: https://doi.org/10.1039/D2CC00522K
Article type: Communication
Submitted: 26 Jan 2022
Accepted: 12 Apr 2022
First published: 12 Apr 2022

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Chem. Commun., 2022,58, 5956-5959

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5-Thiaporphyrinium cation: effect of sulphur incorporation on excited state dynamics

A. Takiguchi, N. Inai, S. Kang, M. Hagai, S. Lee, T. Yanai, D. Kim and H. Shinokubo, Chem. Commun., 2022, 58, 5956 DOI: 10.1039/D2CC00522K

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Chemical Communications

5-Thiaporphyrinium cation: effect of sulphur incorporation on excited state dynamics†

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5-Thiaporphyrinium cation: effect of sulphur incorporation on excited state dynamics

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