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The peculiar spectral properties of amino-substituted uracils: A combined theoretical and experimental study (60 views)

Banyasz A, Karpati S, Mercier Y, Reguero M, Gustavsson T, Markovitsi D, Improta R

J Phys Chem B (ISSN: 1520-6106, 1520-5207, 1520-5207electronic), 2010 Oct 7; 114(39): 12708-12719.

Abstract
A detailed experimental and computational study of the absorption and fluorescence spectra of 5-aminouracil (5 AU) and 6-aminouracil (6 AU) in aqueous solution is reported. The lowest energy band of the steady-state absorption spectra of 5 AU is considerably red-shifted, noticeably less intense, and broader than its counterpart in uracil (U). On the contrary, the 6 AU lowest energy absorption peak is close in energy to that of U, but it is much narrower and the transition is much more intense. The emission properties of 5 AU, 6 AU, and U are also very different. Both amino-substituted compounds exhibit indeed a much larger Stokes shift as compared to U, and the emission band of 5 AU is much narrower than that of 6 AU. Those features are fully rationalized with the help of PCM/TD-PBE0 calculations in aqueous solution and MS-CASPT2/CASSCF calculations in the gas phase. A stable minimum on the potential energy surface of the lowest energy bright state is found for 5 AU, both in the gas phase and in aqueous solution. For 6 AU a barrierless path leads to the conical intersection with the ground electronic state, but a nonplanar plateau region is predicted in aqueous solution, which is responsible for the very large Stokes shift. Some general considerations on the excited-state dynamics of uracil derivatives are also reported. © 2010 American Chemical Society.

Affiliations ▼
*** IBB - CNR Affiliation

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

Departament de Química Física i Inorgànica, Universitat Rovira i Virgili, Marcellí Domingo, S/n-Campus Sescelades, 43007 Tarragona, Spain

Istituto Biostrutture e Bioimmagini-CNR, Via Mezzocannone 16, I-80134 Napoli, Italy

Departament de Qu mica F sica i Inorg nica, Universitat Rovira i Virgili, Marcell Domingo, S/n-Campus Sescelades, 43007 Tarragona, Spain

Details ▼
Impact factor: 3.603, 5-year impact factor: 4.425

Paper type: Journal Article, Research Support, Non-U. S. Gov'T,

Keywords: Gas Absorption, Quantum Chemistry, Solutions, 6-Aminouracil, Absorption And Fluorescence Spectra, Aqueous Solutions, Close-In, Computational Studies, Conical Intersection, Emission Bands, Emission Properties, Energy Band, Excited-State Dynamics, Experimental Studies, Gasphase, Ground Electronic State, Plateau Region, Red-Shifted, Spectral Properties, Steady-State Absorption, Stokes Shift, Substituted Compounds, Substituted Uracils, Uracil Derivatives, Excited States, Models, Theoretical, Quantum Theory, Spectrometry, Thermodynamics, Analogs,

Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-77957315378&partnerID=40&md5=ea9c1e0b3403a42e8d87b352dc5b5421

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3 Records (3 excluding Abstracts and Conferences).
Total impact factor: 17.175 (17.175 excluding Abstracts and Conferences).
Total 5-year impact factor: 17.393 (17.393 excluding Abstracts and Conferences).



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