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Synthesis of D–A–A and D–A–D Pyrimidine π-Systems Using Triorganoindium Reagents: Optical, Vibrational, and Electrochemical Studies
dc.contributor.author | Pérez Caaveiro, Cristina | |
dc.contributor.author | Moreno Oliva, María | |
dc.contributor.author | López Navarrete, Juan Teodomiro | |
dc.contributor.author | Pérez Sestelo, José | |
dc.contributor.author | Martínez, Montserrat | |
dc.contributor.author | Sarandeses, Luis A. | |
dc.date.accessioned | 2024-01-25T16:54:24Z | |
dc.date.issued | 2019-06-26 | |
dc.identifier.citation | Pérez-Caaveiro, C., Oliva, M. M., López Navarrete, J. T., Pérez Sestelo, J., Martínez, M. M., & Sarandeses, L. A. (2019). Synthesis of D–A–A and D–A–D Pyrimidine π-Systems Using Triorganoindium Reagents: Optical, Vibrational, and Electrochemical Studies. The Journal of Organic Chemistry, 84(14), 8870-8885. https://doi.org/10.1021/acs.joc.9b00643 | es_ES |
dc.identifier.issn | 1520-6904 | |
dc.identifier.uri | http://hdl.handle.net/2183/35160 | |
dc.description | This paper is dedicated to Professor Enrique Guitián (Universidade de Santiago de Compostela) | es_ES |
dc.description.abstract | [Abstract] A series of donor–acceptor–acceptor (D–A–A) and donor–acceptor–donor (D–A–D) systems based on a pyrimidine π-spacer with various substituents at the C-2 position has been successfully prepared. The synthesis involved site-selective palladium cross-coupling reactions of chloropyrimidines with triorganoindium reagents and proceed in good yields and with atom economy. 4-(N,N-Diphenylamino)phenyl was chosen as the donor group and thien-2-yl dicyanovinylene as the acceptor one. The optical, vibrational, electrochemical, and density functional theory (DFT) calculations of these molecular systems were analyzed, and experimental values show the important role of the substituents at the C-2 position of the pyrimidine with stronger electron accepting ability, absorption in a wide range of UV/vis, acceptable fluorescence lifetime, and effective intramolecular charge transfer (ICT) properties. The ICT was observed in both series by the bathochromic shift on increasing the polarity of the solvent. In addition, DFT calculations found lower lowest unoccupied molecular orbitals of D–A–A molecules that suggest good electron ejection and transportation, being good properties for their application in various organic optoelectronic devices. | es_ES |
dc.description.sponsorship | We are grateful to the Spanish Ministerio de Economía y Competividad (CTQ2015-68369-P, and CTQ2015-66897-P), Xunta de Galicia (GRC2014/042) and EDRF funds for financial support. M.M.O. thanks the MINECO for a “Juan de la Cierva-Incorporación” research contract. We also acknowledge Prof. D. Pérez (Universidade de Santiago de Compostela) for her collaboration in CV-measures and the assistance of Prof. A. Fernández (Universidade da Coruña) for processing the X-ray data | es_ES |
dc.description.sponsorship | Xunta de Galicia; GRC2014/042 | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | American Chemical Society (ACS) | es_ES |
dc.relation | info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2015-68369-P/ES/INDIO EN REACCIONES DE ACOPLAMIENTO Y CATALISIS: ESTRUCTURA, REACTIVIDAD Y APLICACIONES SINTETICAS/ | es_ES |
dc.relation | info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2015-66897-P/ES/ESTUDIO ESPECTROSCOPICO Y TEORICO DE MATERIALES ORGANICOS PARA ELECTRONICA MOLECULAR: DE LA MOLECULA AL DISPOSITIVO/ | es_ES |
dc.relation.uri | https://doi.org/10.1021/acs.joc.9b00643 | es_ES |
dc.rights | Copyright © 2019 American Chemical Society | es_ES |
dc.subject | Cross coupling reaction | es_ES |
dc.subject | Fluorescence | es_ES |
dc.subject | Molecules | es_ES |
dc.subject | Oxidation | es_ES |
dc.subject | Pyrimidine | es_ES |
dc.title | Synthesis of D–A–A and D–A–D Pyrimidine π-Systems Using Triorganoindium Reagents: Optical, Vibrational, and Electrochemical Studies | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.access | info:eu-repo/semantics/embargoedAccess | es_ES |
dc.date.embargoEndDate | 9999-99-99 | es_ES |
dc.date.embargoLift | 10007-06-07 | |
UDC.journalTitle | The Journal of Organic Chemistry | es_ES |
UDC.volume | 84 (2019) | es_ES |
UDC.issue | 14 | es_ES |
UDC.startPage | 8870 | es_ES |
UDC.endPage | 8885 | es_ES |
dc.identifier.doi | 10.1021/acs.joc.9b00643 |
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