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Issue 5, 2013
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Tuning photoinduced processes of covalently bound isoalloxazine and anthraquinone bichromophores

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Abstract

We present here the synthesis of several new isoalloxazine cyclophanes containing electroactive anthraquinones linked by aliphatic chains of different lengths. Such structural changes provide different interchromophoric orientations leading to the tuning of the rate of the photoinduced electron transfer process from the anthraquinone unit towards the isoalloxazine singlet excited state. Molecular modelling studies were undertaken in order to determine the minimal energy of the proposed structures using Monte Carlo calculations (Amber, Macromodel v.8.1). The compounds have been fully characterised by NMR spectroscopy and the solid state structures of some of the macrocycles have been elucidated. The photophysical studies have been carried out in order to investigate the influence of π–π stacking on the optical properties of the macrocycles.

Graphical abstract: Tuning photoinduced processes of covalently bound isoalloxazine and anthraquinone bichromophores

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Supplementary files

Article information


Submitted
25 Sep 2012
Accepted
14 Jan 2013
First published
15 Jan 2013

Photochem. Photobiol. Sci., 2013,12, 813-822
Article type
Paper

Tuning photoinduced processes of covalently bound isoalloxazine and anthraquinone bichromophores

A. Farrán, J. Mohanraj, G. J. Clarkson, R. M. Claramunt, F. Herranz and G. Accorsi, Photochem. Photobiol. Sci., 2013, 12, 813
DOI: 10.1039/C3PP25321J

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