Simultaneous Implementation of N-Heterocycle-Fused Bridge and Modified Pyrrole Unit on Ni(II) Porphyrin Dimers

Yuanyuan Li; Mingbo Zhou; Ling Xu; Bixiang Zhou; Yutao Rao; Haigen Nie; Tingting Gu; Jie Zhou; Xu Liang; Bangshao Yin; Weihua Zhu; Atsuhiro Osuka; Jianxin Song

doi:10.1021/acs.orglett.0c02084

Simultaneous Implementation of N-Heterocycle-Fused Bridge and Modified Pyrrole Unit on Ni(II) Porphyrin Dimers

Org Lett. 2020 Aug 7;22(15):6001-6005. doi: 10.1021/acs.orglett.0c02084. Epub 2020 Jul 21.

Authors

Yuanyuan Li¹, Mingbo Zhou¹, Ling Xu¹, Bixiang Zhou¹, Yutao Rao¹, Haigen Nie¹, Tingting Gu², Jie Zhou¹, Xu Liang², Bangshao Yin¹, Weihua Zhu², Atsuhiro Osuka¹, Jianxin Song¹

Affiliations

¹ Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education of China, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha, Hunan 410081, P. R. China.
² School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, P. R. China.

PMID: 32692918
DOI: 10.1021/acs.orglett.0c02084

Abstract

The oxidation of Ni^II-porphyrin dimer 10 with PbO₂ or MnO₂ resulted in the simultaneous implementation of an N-heterocycle-fused bridge and a modified pyrrole to give three unprecedented porphyrin dimers 11, 12, and 13. The reduction of 12 smoothly afforded 14. The structures of these dimers were all unambiguously confirmed by X-ray crystallographic analysis. These dimers show significantly red-shifted absorption bands and perturbed electrochemical properties with a decreasing HOMO-LUMO gap in the order of 14 > 13 > 11 > 12.

Publication types

Research Support, Non-U.S. Gov't