Highly effective quenching of the ultrafast radiationless decay of photoexcited pyrimidine bases by covalent modification: photophysics of 5,6-trimethylenecytosine and 5,6-trimethyleneuracil

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DOIResolve DOI: http://doi.org/10.1039/b704001f
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TypeArticle
Journal titlePhys. Chem. Chem. Phys.
Physical Chemistry Chemical Physics
Volume9
Issue25
Pages32063209; # of pages: 4
Abstract5,6-Trimethylenecytosine (TMC) and 5,6-trimethyleneuracil (TMU), in which the twist of the C5-C6 bond (or the pyrimidalization of C5) is strongly hindered, do not exhibit the subpicosecond excited-state lifetime characteristic of the naturally occurring pyrimidine bases. This result demonstrates the important role the out-of-plane deformation of the six-membered ring plays in the ultrafast (subpicosecond) internal conversion of photoexcited nucleobases. The dramatically shorter fluorescence lifetime of TMU ([similar]30 ps) relative to TMC ([similar]1.2 ns), in aqueous solution at room temperature, is attributed to the presence in TMU of an efficient, secondary nonradiative decay channel of S1([small pi][small pi]*) involving a low-lying 1n[small pi]* state.
Publication date
AffiliationNational Research Council Canada; NRC Steacie Institute for Molecular Sciences
Peer reviewedNo
NPARC number12339091
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Record identifier63af80a7-c137-4f1b-a80b-0a0eeb00daa4
Record created2009-09-11
Record modified2016-05-09
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