Porphyrin and Phthalocyanine Chemistry Peer reviewed

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

Jin Zhong, Jinying Ren, Yuqin Zhu, Fujie He and 6 more

Organic Letters | Aug 21, 2026

Abstract

Abstract

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.

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Authors

Researchers on this paper

Jin Zhong

first | Hunan Normal University

Jinying Ren

middle | Hunan Normal University

Yuqin Zhu

middle | Hunan Normal University

Fujie He

middle | Hunan Normal University

Yuanyuan Jiang

middle | Hunan Normal University | ORCID 0000-0001-8594-6046

Yutao Rao

middle | Hunan Normal University | ORCID 0009-0001-6578-6505

Mingbo Zhou

middle | Hunan Normal University

Atsuhiro Osuka

middle | Hunan Normal University | ORCID 0000-0001-8697-8488

Ling Xu

middle | Hunan Normal University | ORCID 0000-0002-3126-5787

Jianxin Song

last | Hunan Normal University | ORCID 0000-0002-1756-5898

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Citation

BibTeX

@article{Zhong2026Global,
  title = {Global Antiaromaticity Induced by Installation of 3,5-Di(pyrrol-2-yl)BODIPY across the meso Position of Porphyrinoids},
  author = {Jin Zhong and Jinying Ren and Yuqin Zhu and Fujie He and Yuanyuan Jiang and Yutao Rao and Mingbo Zhou and Atsuhiro Osuka and Ling Xu and Jianxin Song},
  journal = {Organic Letters},
  year = {2026},
  doi = {10.1021/acs.orglett.6c03188},
  url = {https://doi.org/10.1021/acs.orglett.6c03188}
}

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