Unique Role of Heterole-Fused Structures in Aromaticity and Physicochemical Properties of 7,8-Dehydropurpurins.

aromaticity nitrogen phosphole porphyrinoid pyrrole

Journal

Chemistry (Weinheim an der Bergstrasse, Germany)

ISSN: 1521-3765

Titre abrégé: Chemistry

Pays: Germany

ID NLM: 9513783

Informations de publication

Date de publication:
16 Sep 2020

Historique:

received: 18 03 2020

pubmed: 28 4 2020

medline: 28 4 2020

entrez: 28 4 2020

Statut: ppublish

Résumé

Porphyrins with a fused five-membered ring, such as 7,8-dehydropurpurins, have appeared as an emerging class of unique porphyrinoids. Their altered absorption spectra, relatively short lifetimes of excited states, and small HOMO-LUMO gaps arise from the harmony of the antiaromatic 20π-circuit and the aromatic 18π-circuit. In this regard, the electronic properties of 7,8-dehydropurpurins are expected to be controlled by modulating the contribution of the antiaromatic π-circuit to the whole aromaticity. Here the comparison of pyrrole- and phosphole-fused 7,8-dehydropurpurins is reported in terms of their aromaticity and physicochemical properties. The spectroscopic investigation revealed the larger contribution of the antiaromatic 24π-circuit in pyrrole-fused 7,8-dehyrdopurpurins than in phosphole-fused 7,8-dehydropurpurins. The DFT calculations also supported the feasibility of tuning the aromaticity of 7,8-dehydropurpurins by heterole-fused structures. Thus, the introduction of heterole-fused structures into porphyrinoids is a universal strategy to get new insight into aromaticity and their intrinsic properties in cyclic π-conjugated molecules.

Identifiants

DOI: 10.1002/chem.202001361 PMID: 32338789

pubmed: 32338789

doi: 10.1002/chem.202001361

doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

Pagination

12043-12049

Subventions

Organisme : Japan Society for the Promotion of Science

ID : JP18H03898

Organisme : Japan Society for the Promotion of Science

ID : JP18K14198

Informations de copyright

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