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Singlet excited-state behavior of uracil and thymine in aqueous solution: A combined experimental and computational study of 11 uracil derivatives (96 views)

Gustavsson T, Banyasz A, Lazzarotto E, Markovitsi D, Scalmani G, Frisch MJ, Barone V, Improta R

J Am Chem Soc (ISSN: 0002-7863, 0002-2786, 1520-5126), 2006 Jan 18; 128(2): 607-619.

Abstract
The excited-state properties of uracil, thymine, and nine other derivatives of uracil have been studied by steady-state and time-resolved spectroscopy. The excited-state lifetimes were measured using femtosecond fluorescence upconversion in the UV. The absorption and emission spectra of five representative compounds have been computed at the TD-DFT level, using the PBEO exchange-correlation functional for ground- and excited-state geometry optimization and the Polarizable Continuum Model (PCM) to simulate the aqueous solution. The calculated spectra are in good agreement with the experimental ones. Experiments show that the excited-state lifetimes of all the compounds examined are dominated by an ultrafast (<100 fs) component. Only 5-substituted compounds show more complex behavior than uracil, exhibiting longer excited-state lifetimes and biexponential fluorescence decays. The S 0/S 1 conical intersection, located at CASSCF (8/8) level, is indeed characterized by pyramidalization and out of plane motion of the substituents on the C5 atom. A thorough analysis of the excited-state Potential Energy Surfaces, performed at the PCM/TD-DFT(PBE0) level in aqueous solution, shows that the energy barrier separating the local S 1 minimum from the conical intersection increases going from uracil through thymine to 5-fluorouracil, in agreement with the ordering of the experimental excited-state lifetime. © 2006 American Chemical Society.

Affiliations ▼
*** IBB - CNR Affiliation

Laboratoire Francis Perrin, CEA/DSM/DRECAM/SPAM - CNRS URA 2453, CEA Saclay, F-91191 Gif-sur-Yvette, France

Gaussian, Inc., Bldg. 40, 340 Quinnipiac St., Wallingford, CT 06492, United States

Dipartimento di Chimica, Universita Federico II, Complesso Universitario Monte S. Angelo, Via Cintia, I-80126 Napoli, Italy

Istituto Biostrutture e Bioimmagini/CNR, V. Mezzocannone 6, 80134 Napoli, Italy

Research Institute for Solid State Physics and Optics, Hungarian Academy of Sciences, P.O. Box 49, Budapest H 1525, Hungary

Details ▼
Impact factor: 7.696, 5-year impact factor: 11.015

Paper type: Journal Article,

Keywords: Computer Simulation, Correlation Methods, Derivatives, Fluorescence, Ground State, Optimization, Probability Density Function, Solutions, Spectroscopic Analysis, 5-Fluorouracil, Polarizable Continuum Model (pcm), Pyramidalization, Organic Compounds, 1 Methylthymine, 1 Methyluracil, 3 Dimethyluracil, 3 Methyluracil, 5 Chlorouracil Derivative, 5 Fluoro 1, 5 Trifluoromethyluracil, 6 Methyluracil, Unclassified Drug, Aqueous Solution, Article, Density Functional Theory, Energy, Geometry, Molecular Model, Spectrometry, Thermodynamics, Water,

Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-31544440193&partnerID=40&md5=a7fc0d993c67a2c34e0c0339bbc44818

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1 Records (0 excluding Abstracts and Conferences).
Total impact factor: 1.461 (0 excluding Abstracts and Conferences).
Total 5-year impact factor: 1.721 (0 excluding Abstracts and Conferences).



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