Abstract
The electron-hole injection from a family of spiropyran photoswitches into A/T-duplex DNA has been investigated at the molecular level for the first time. Multiscale computations coupled with automatized quantitative wavefunction analysis reveal a pronounced directionality and regioselectivity towards the template strand of the duplex DNA. Our findings suggest that this directional and regioselective photoinduced electron-hole transfer could thus be exploited to tailor the charge transport processes in DNA in specific applications.
Highlights
The electron-hole injection from a family of spiropyran photoswitches into A/T-duplex DNA has been investigated at the molecular level for the first time
We use atomistic multiscale calculations coupled with quantitative wavefunction analysis to model explicitly the hole injection from two MCH derivatives (2a and 2b) into 12-mer[2], for which these compounds show selectivity.[24]
A total of 4000 excited states per complex were calculated within a quantum mechanics/molecular mechanics (QM/MM) framework, where the chromophore and the first four surrounding nucleobases (121 atoms for 2a:DNA and 125 atoms for 2b:DNA, see Fig. 1a and b) are considered quantum mechanically
Summary
Directional and regioselective hole injection of spiropyran photoswitches intercalated into A/T-duplex DNA†. SPs undergo heterocyclic cleavage to yield the open merocyanine (MC) form.[22,23] the SP form (1 in Scheme 1) does not bind DNA but the protonated open MCH form (2) does.[24,25] While the photocleavage of SP in solution has been widely investigated,[26,27,28,29,30,31] and it is known that the protonated open MCH form is able to oxidize DNA nucleobases in cell culture,[32] the excited states of these photoswitches intercalated in DNA have never been investigated This is the subject of this work. The CT character, defined by the CT number[37] from 0 to 1, measures the intermolecular light-driven electron transfer
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