Protonation-Triggered Hückel and Möbius Aromatic Transformations in Nonaromatic Core-Modified [30]Hexaphyrin(2.1.1.2.1.1) and Annulated [28]Hexaphyrin(2.1.1.0.1.1)

Dash, Syamasrit ; Ghosh, Arindam ; Srinivasan, A. ; Suresh, Cherumuttathu H. ; Chandrashekar, Tavarekere K. (2019) Protonation-Triggered Hückel and Möbius Aromatic Transformations in Nonaromatic Core-Modified [30]Hexaphyrin(2.1.1.2.1.1) and Annulated [28]Hexaphyrin(2.1.1.0.1.1) Organic Letters, 21 (23). pp. 9637-9641. ISSN 1523-7060

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Official URL: http://doi.org/10.1021/acs.orglett.9b03805

Related URL: http://dx.doi.org/10.1021/acs.orglett.9b03805

Abstract

Two 1,2-diphenyl-1,2-dithienylethene-embedded hexaphyrins 6 and 8 containing 30π and 28π electrons, respectively, in conjugation exhibit nonaromatic characteristics. Compound 6 shows an unusual bond length equalization in its electronic structure. However, on protonation, 6 exhibits Hückel aromatic characteristics while 8 shows Möbius aromatic characteristics. The changes in aromaticity are accompanied by change in conformation from a figure-eight/twisted structure to an open extended structure.

Item Type:Article
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ID Code:134873
Deposited On:16 Jan 2023 04:42
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