Tuning photoinduced processes of covalently bound isoalloxazine and anthraquinone bichromophoresElectronic supplementary information (ESI) available: Details of X-ray crystallography, NMR spectroscopy and optimized conformations of compounds MA and MQ. CCDC 894359-894361. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c3pp25321j

• Main Authors: Farrán, Angeles, Mohanraj, John, Clarkson, Guy J, Claramunt, Rosa M, Herranz, Fernando, Accorsi, Gianluca
• Format: Article
• Language: English
• ISSN: 1474-905X; 1474-9092
• DOI: 10.1039/c3pp25321j

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. We present here the synthesis of several new isoalloxazine cyclophanes containing electroactive anthraquinones linked by aliphatic chains of different lengths.