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Highly effective quenching of the ultrafast radiationless decay of photoexcited pyrimidine bases by covalent modification: photophysics of 5,6-trimethylenecytosine and 5,6-trimethyleneuracil.
Phys Chem Chem Phys. 2007 Jul 07; 9(25):3206-9.PC

Abstract

5,6-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 (approximately 30 ps) relative to TMC (approximately 1.2 ns), in aqueous solution at room temperature, is attributed to the presence in TMU of an efficient, secondary nonradiative decay channel of S(1)(pipi*) involving a low-lying (1)npi* state.

Authors+Show Affiliations

Steacie Institute for Molecular Sciences, National Research Council of Canada, Ottawa, K1A 0R6, Canada.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

17579729

Citation

Zgierski, Marek Z., et al. "Highly Effective Quenching of the Ultrafast Radiationless Decay of Photoexcited Pyrimidine Bases By Covalent Modification: Photophysics of 5,6-trimethylenecytosine and 5,6-trimethyleneuracil." Physical Chemistry Chemical Physics : PCCP, vol. 9, no. 25, 2007, pp. 3206-9.
Zgierski MZ, Fujiwara T, Kofron WG, et al. Highly effective quenching of the ultrafast radiationless decay of photoexcited pyrimidine bases by covalent modification: photophysics of 5,6-trimethylenecytosine and 5,6-trimethyleneuracil. Phys Chem Chem Phys. 2007;9(25):3206-9.
Zgierski, M. Z., Fujiwara, T., Kofron, W. G., & Lim, E. C. (2007). Highly effective quenching of the ultrafast radiationless decay of photoexcited pyrimidine bases by covalent modification: photophysics of 5,6-trimethylenecytosine and 5,6-trimethyleneuracil. Physical Chemistry Chemical Physics : PCCP, 9(25), 3206-9.
Zgierski MZ, et al. Highly Effective Quenching of the Ultrafast Radiationless Decay of Photoexcited Pyrimidine Bases By Covalent Modification: Photophysics of 5,6-trimethylenecytosine and 5,6-trimethyleneuracil. Phys Chem Chem Phys. 2007 Jul 7;9(25):3206-9. PubMed PMID: 17579729.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly effective quenching of the ultrafast radiationless decay of photoexcited pyrimidine bases by covalent modification: photophysics of 5,6-trimethylenecytosine and 5,6-trimethyleneuracil. AU - Zgierski,Marek Z, AU - Fujiwara,Takashige, AU - Kofron,William G, AU - Lim,Edward C, Y1 - 2007/05/25/ PY - 2007/6/21/pubmed PY - 2007/10/20/medline PY - 2007/6/21/entrez SP - 3206 EP - 9 JF - Physical chemistry chemical physics : PCCP JO - Phys Chem Chem Phys VL - 9 IS - 25 N2 - 5,6-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 (approximately 30 ps) relative to TMC (approximately 1.2 ns), in aqueous solution at room temperature, is attributed to the presence in TMU of an efficient, secondary nonradiative decay channel of S(1)(pipi*) involving a low-lying (1)npi* state. SN - 1463-9076 UR - https://www.unboundmedicine.com/medline/citation/17579729/Highly_effective_quenching_of_the_ultrafast_radiationless_decay_of_photoexcited_pyrimidine_bases_by_covalent_modification:_photophysics_of_56_trimethylenecytosine_and_56_trimethyleneuracil_ L2 - https://doi.org/10.1039/b704001f DB - PRIME DP - Unbound Medicine ER -