Nonalternant Acenaphthylene-Fused Carbaporphyrins: Topological Modulation of π-Delocalization, (Anti)aromaticity, and B <sup>III</sup> Coordination

Acenaphthylene (AN) fusion at the <i>meso</i>-position served as a structural and electronic modulator in carbaporphyrinoids, where the isomeric homocarbaporphyrinoids and their B<sup>III</sup> complexes remain nonaromatic due to electronic decoupling or nonplanarity. In contrast, the isolated [24]carbapentaphyrin(2.1.1.1.1) sustained global antiaromaticity. These findings confirm that AN fusion is an advantageous strategy for designing nonclassical porphyrinoid architectures with tunable (anti)aromatic properties.

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Journal
Organic Letters
Published
2025-10-20
DOI
https://doi.org/10.1021/acs.orglett.5c03800
Primary Topic
Porphyrin and Phthalocyanine Chemistry
Type
article
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article

Nonalternant Acenaphthylene-Fused Carbaporphyrins: Topological Modulation of π-Delocalization, (Anti)aromaticity, and B III Coordination

Mainak Das, Arumugam Kalaiselvan, A. Srinivasan, Chetan Kumar Prasad et al.
Organic Letters
Porphyrin and Phthalocyanine Chemistry
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Nonalternant Acenaphthylene-Fused Carbaporphyrins: Topological Modulation of π-Delocalization, (Anti)aromaticity, and B III Coordination

Mainak Das, Arumugam Kalaiselvan, A. Srinivasan, Chetan Kumar Prasad, Shambhavi Sah
article en

Abstract

Acenaphthylene (AN) fusion at the <i>meso</i>-position served as a structural and electronic modulator in carbaporphyrinoids, where the isomeric homocarbaporphyrinoids and their B<sup>III</sup> complexes remain nonaromatic due to electronic decoupling or nonplanarity. In contrast, the isolated [24]carbapentaphyrin(2.1.1.1.1) sustained global antiaromaticity. These findings confirm that AN fusion is an advantageous strategy for designing nonclassical porphyrinoid architectures with tunable (anti)aromatic properties.

Organic LettersVol. 27(43)
Centre National de la Recherche Scientifique (FR), National Institute of Science Education and Research (IN), Homi Bhabha National Institute (IN), Sorbonne Université (FR), Institut Parisien de Chimie Moléculaire (FR)
Openalex Percentile: Top 77%
Porphyrin and Phthalocyanine Chemistry
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