Synthesis of D–A–A and D–A–D Pyrimidine π-Systems Using Triorganoindium Reagents: Optical, Vibrational, and Electrochemical Studies
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Synthesis of D–A–A and D–A–D Pyrimidine π-Systems Using Triorganoindium Reagents: Optical, Vibrational, and Electrochemical StudiesAuthor(s)
Date
2019-06-26Citation
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
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.
Keywords
Cross coupling reaction
Fluorescence
Molecules
Oxidation
Pyrimidine
Fluorescence
Molecules
Oxidation
Pyrimidine
Description
This paper is dedicated to Professor Enrique Guitián (Universidade de Santiago de Compostela)
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Copyright © 2019 American Chemical Society
ISSN
1520-6904