Deprotection of a benzyl unit induces a 22π aromatic macrocycle of 3-oxypyripentaphyrin(0.1.1.1.0) with strong NIR absorption

Daiki Mori; Tomoki Yoneda; Masaaki Suzuki; Tyuji Hoshino; Saburo Neya

doi:10.1039/D0OB01213K

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Deprotection of a benzyl unit induces a 22π aromatic macrocycle of 3-oxypyripentaphyrin(0.1.1.1.0) with strong NIR absorption†

Daiki Mori,^a Tomoki Yoneda,

*^ab Masaaki Suzuki,^c Tyuji Hoshino

^a and Saburo Neya*^a

Author affiliations

* Corresponding authors

^a Department of Pharmaceutical Sciences, Chiba University, Inohana, Chuo-ku, Chiba, Japan

^b Division of Applied Chemistry, Faculty of Engineering, Hokkaido University, Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido, Japan
E-mail: t_yoneda@eng.hokudai.ac.jp

^c Graduate School of Natural Science and Technology, Shimane University, 1060, Nishikawatsu-cho, Matsue, Shimane, Japan

Abstract

We report aromaticity switching from a 6π pyridine ring to a 22π macrocyclic ring of 3-oxypyripentaphyrin(0.1.1.1.0). This system has potential applications in photodynamic therapy owing to macrocyclic aromaticity being selectively induced by protecting group removal and strong absorption bands produced in the NIR region especially in methanol.

This article is part of the themed collection: Supramolecular chemistry in OBC

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DOI: https://doi.org/10.1039/D0OB01213K
Article type: Communication
Submitted: 12 Jun 2020
Accepted: 22 Jun 2020
First published: 22 Jun 2020

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Org. Biomol. Chem., 2020,18, 5334-5338

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Deprotection of a benzyl unit induces a 22π aromatic macrocycle of 3-oxypyripentaphyrin(0.1.1.1.0) with strong NIR absorption

D. Mori, T. Yoneda, M. Suzuki, T. Hoshino and S. Neya, Org. Biomol. Chem., 2020, 18, 5334 DOI: 10.1039/D0OB01213K

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Organic & Biomolecular Chemistry

Deprotection of a benzyl unit induces a 22π aromatic macrocycle of 3-oxypyripentaphyrin(0.1.1.1.0) with strong NIR absorption†

Abstract

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Deprotection of a benzyl unit induces a 22π aromatic macrocycle of 3-oxypyripentaphyrin(0.1.1.1.0) with strong NIR absorption

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