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Fluorescent excimers and exciplexes of the purine base derivative 8-phenylethynyl-guanine in DNA hairpins

Brown, Kristen E., Singh, Arunoday P. N., Wu, Yi-Lin ORCID:, Ma, Lin, Mishra, Ashutosh K., Phelan, Brian T., Young, Ryan M., Lewis, Frederick D. and Wasielewski, Michael R. 2017. Fluorescent excimers and exciplexes of the purine base derivative 8-phenylethynyl-guanine in DNA hairpins. Faraday Discussions 207 , pp. 217-232. 10.1039/C7FD00186J

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The ground- and excited-state electronic interactions between the nucleobase analog 8-(4′-phenylethynyl)deoxyguanosine, EG, with natural nucleobases and 7-deazaguanine, as well as between adjacent EG base analogs, have been characterized using a combination of steady-state spectroscopy and time-resolved fluorescence, absorption, and stimulated Raman spectroscopies. The properties of the nucleoside EG-H2 are only weakly perturbed upon incorporation into synthetic DNA hairpins in which thymine, cytosine or adenine are the bases flanking EG. Incorporation of the nucleoside to be adjacent to guanine or deazaguanine results in the formation of short-lived (40–80 ps) exciplexes, the charge transfer character of which increases as the oxidation potential of the donor decreases. Hairpins possessing two or three adjacent EG base analogs display exciton-coupled circular dichroism in the ground state and form long-lived fluorescent excited states upon electronic excitation. Incorporation of EG into the helical scaffold of the DNA hairpins places it adjacent to its neighboring nucleobases or a second EG, thus providing the close proximity required for the formation of exciplex or excimer intermediates upon geometric relaxation of the short-lived EG excited state. The three time-resolved spectroscopic methods employed permit both the characterization of the several intermediates and the kinetics of their formation and decay.

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Chemistry
Publisher: Royal Society of Chemistry
ISSN: 1359-6640
Date of First Compliant Deposit: 11 January 2019
Date of Acceptance: 1 September 2017
Last Modified: 07 Nov 2023 06:03

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