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Chemistry. 2014 Feb 10;20(7):1985-97. doi: 10.1002/chem.201303676. Epub 2014 Jan 15.

Hückel and Möbius expanded para-benziporphyrins: synthesis and aromaticity switching.

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  • 1Department of Chemistry, University of Wrocław, 14 F. Joliot-Curie St., 50-383 Wrocław (Poland), Fax: (+48) 71-328-23-48.

Abstract

The four expanded p-benziporphyrins A,C-di-p-benzi[24]pentaphyrin(1.1.1.1.1), N-fused A-p-benzi[24]pentaphyrin, A,D-di-p-benzi[28]hexaphyrin(1.1.1.1.1.1), and A,C-di-p-benzi[28]hexaphyrin(1.1.1.1.1.1) were obtained in three-component Lindsey-type macrocyclizations. These compounds were explored as macrocyclic ligands and as potential aromaticity switches. A BODIPY-like difluoroboron complex was obtained from the A,C-di-p-benzi[24]pentaphyrin, whereas A,C-di-p-benzi[28]hexaphyrin yielded a Möbius-aromatic Pd(II) complex containing fused pyrrole and phenylene subunits. Conformational behavior, tautomerism, and acid-base chemistry of the new macrocycles were characterized by means of NMR spectroscopy and DFT calculations. Free base N-fused A-p-benzi[24]pentaphyrin showed temperature-dependent Hückel-Möbius aromaticity switching, whereas the A,C-di-p-benzi[28]hexaphyrin formed a Möbius-aromatic dication.

Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KEYWORDS:

NMR spectroscopy; aromaticity; conjugation; density functional calculations; porphyrinoids

PMID:
24431244
[PubMed]
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