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Issue 3, 2015
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5,20-Bis(α-oligothienyl)-substituted [26]hexaphyrins possessing electronic circuits strongly perturbed by meso-oligothienyl substituents

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Abstract

A series of [26]hexaphyrins(1.1.1.1.1.1) bearing two α-oligothienyl substituents at 5,20-positions have been synthesised and are shown to have a dumbbell hexaphyrin conformation, to which the α-oligothienyl groups are linked with small dihedral angles to form an acyclic helix-like conjugated network. While their distinct diatropic ring currents and four reversible reduction waves characteristic of aromatic [26]hexaphyrins indicate that the [26]hexaphyrin aromatic circuits are viable, the absorption spectra and excited state dynamics are significantly perturbed, which becomes increasingly evident with elongation of the oligothienyl substituents. DFT calculations of these hexaphyrins indicated that the LUMO and LUMO + 1 are localised on the hexaphyrin circuit and the HOMO and HOMO − 1 are spread over the acyclic helix-like conjugation network, which can explain the perturbed absorption spectra.

Graphical abstract: 5,20-Bis(α-oligothienyl)-substituted [26]hexaphyrins possessing electronic circuits strongly perturbed by meso-oligothienyl substituents

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Article information


Submitted
05 Nov 2014
Accepted
30 Nov 2014
First published
02 Dec 2014

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 1696-1700
Article type
Edge Article
Author version available

5,20-Bis(α-oligothienyl)-substituted [26]hexaphyrins possessing electronic circuits strongly perturbed by meso-oligothienyl substituents

H. Mori, M. Suzuki, W. Kim, J. M. Lim, D. Kim and A. Osuka, Chem. Sci., 2015, 6, 1696
DOI: 10.1039/C4SC03394A

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