Global Antiaromaticity Induced by Installation of 3,5-Di(pyrrol-2-yl)BODIPY across the meso Position of Porphyrinoids

Organic Letters 2026

View at publisher
Authors: Jin Zhong, Jinying Ren, Yuqin Zhu, Fujie He, Yuanyuan Jiang, Yutao Rao, Mingbo Zhou, Atsuhiro Osuka, Ling Xu, Jianxin Song
DOI: 10.1021/acs.orglett.6c03188
Cited by: 1
References: 45

Abstract

Installations of the 3,5-di(pyrrol-2-yl)BODIPY strap across the meso position of B(III) submonoazaporphyrin, B(III) subporphyrin, and Ni(II) porphyrin resulted in the formation of expanded porphyrins with a dual electronic network consisting of a local diatropic ring current of the original aromatic segments and a newly formed global paratropic ring current as evinced by 1H NMR spectroscopy, UV-vis-NIR absorption spectra, small electrochemical HOMO-LUMO gaps, and NICS and ACID calculations. This synthetic protocol is useful for modulating the aromatic character of meso-aza and meso-free aromatic porphyrinoids.

Fields of Study & Subjects

Porphyrin and Phthalocyanine Chemistry Luminescence and Fluorescent Materials Photodynamic Therapy Research Studies

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
35
Pages
11082–11086
Publication date
21 August 2026
Language
EN