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Excited State Lifetimes of Sulfur-Substituted DNA and RNA Monomers Probed Using the Femtosecond Fluorescence Up-Conversion Technique
Open AccessArticle

Excited State Dynamics of 8-Vinyldeoxyguanosine in Aqueous Solution Studied by Time-Resolved Fluorescence Spectroscopy and Quantum Mechanical Calculations

1
Departamento de Química, Facultad de Ciencias and IADCHEM (Institute for Advanced Research in Chemistry) Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
2
Université Paris-Saclay, CEA, CNRS, LIDYL, 91191 Gif-sur-Yvette, France
3
Univ Goettingen, Inst Organ & Biomol Chem, Tammannstr 2, D-37077 Goettingen, Germany
4
Istituto di Biostrutture e Bioimmagini, CNR, Via Mezzocannone 16, I-80134 Napoli, Italy
*
Authors to whom correspondence should be addressed.
Molecules 2020, 25(4), 824; https://doi.org/10.3390/molecules25040824 (registering DOI)
Received: 28 January 2020 / Revised: 10 February 2020 / Accepted: 10 February 2020 / Published: 13 February 2020
(This article belongs to the Special Issue Fluorescence Spectroscopy of Biomolecules)
The fluorescent base guanine analog, 8-vinyl-deoxyguanosine (8vdG), is studied in solution using a combination of optical spectroscopies, notably femtosecond fluorescence upconversion and quantum chemical calculations, based on time-dependent density functional theory (TD-DFT) and including solvent effect by using a mixed discrete-continuum model. In all investigated solvents, the fluorescence is very long lived (3–4 ns), emanating from a stable excited state minimum with pronounced intramolecular charge-transfer character. The main non-radiative decay channel features a sizeable energy barrier and it is affected by the polarity and the H-bonding properties of the solvent. Calculations provide a picture of dynamical solvation effects fully consistent with the experimental results and show that the photophysical properties of 8vdG are modulated by the orientation of the vinyl group with respect to the purine ring, which in turn depends on the solvent. These findings may have importance for the understanding of the fluorescence properties of 8vdG when incorporated in a DNA helix. View Full-Text
Keywords: DNA; solvent effect; TD-DFT; fluorescent probe DNA; solvent effect; TD-DFT; fluorescent probe
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Martinez-Fernandez, L.; Gustavsson, T.; Diederichsen, U.; Improta, R. Excited State Dynamics of 8-Vinyldeoxyguanosine in Aqueous Solution Studied by Time-Resolved Fluorescence Spectroscopy and Quantum Mechanical Calculations. Molecules 2020, 25, 824.

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