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Issue 7, 2008
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Tuning energy transfer in switchable donor–acceptor systems

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The synthesis and characterisation of a coumarin–dithienylcyclopentene–coumarin symmetric triad (CSC) and a perylene bisimide–dithienylcyclopentenecoumarin asymmetric triad (PSC) are reported. In both triads the switching function of the photochromic dithienylcyclopentene unit is retained. For CSC an overall 50% quenching of the coumarin fluorescence is observed upon ring-closure of the dithienylcyclopentene component, which, taken together with the low PSS (<70%), indicates that energy transfer quenching of the coumarin component by the dithienylcyclopentene in the closed state is efficient. Upon ring opening of the dithienylcyclopentene unit the coumarin emission is restored fully. The PSC triad shows efficient energy transfer from the coumarin to the perylene bisimide unit when the dithienylcyclopentene unit is in the open state. When the dithienylcyclopentene is in the closed (PSS) state a 60% decrease in sensitized perylene bisimide emission intensity is observed due to competitive quenching of the coumarin excited state and partial quenching of the perylene excited state by the closed dithienylcyclopentene unit. This modulation of energy transfer is reversible over several cycles for both the symmetric and asymmetric tri-component systems.

Graphical abstract: Tuning energy transfer in switchable donor–acceptor systems

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Article information

11 Dec 2007
23 Jan 2008
First published
21 Feb 2008

Org. Biomol. Chem., 2008,6, 1268-1277
Article type

Tuning energy transfer in switchable donor–acceptor systems

J. H. Hurenkamp, J. J. D. de Jong, W. R. Browne, J. H. van Esch and B. L. Feringa, Org. Biomol. Chem., 2008, 6, 1268
DOI: 10.1039/B719095F

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