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Title: 2-Chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]styryl}pyrimidine: Synthesis, Spectroscopic and Computational Evaluation
Authors: Chaves, Otávio Augusto 
Sueth-Santiago, Vitor
Pinto, Douglas Chaves de Alcântara
Netto-Ferreira, José Carlos
Decote-Ricardo, Debora
Lima, Marco Edilson Freire de
Keywords: curcumin analog; organic synthesis; photophysical properties; steady-state fluorescence; DFT calculation
Issue Date: 2021
Project: (CAPES) Coordenação de Aperfeiçoamento de Pessoal de Nível Superior 
(CNPq) Conselho Nacional de Desenvolvimento Científico e Tecnológico 
(FAPER) Fundação Carlos Chagas Filho de Amparo à Pesquisa do Estado do Rio de Janeiro 
FCT PhD fellowship 2020.07504.BD 
Serial title, monograph or event: MolBank
Volume: 2021
Issue: 3
Abstract: A novel curcumin analog namely 2-chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]- styryl}pyrimidine (compound 7) was synthesized by three-step reaction. The condensation reaction of protected vanillin with 2-chloro-4,6-dimethylpyrimidine (6) was the most efficient step, resulting in a total yield of 72%. The characterization of compound 7was performed by 1Hand 13C nuclearmagnetic resonance (NMR), as well as high-resolution mass spectrometry. The experimental spectrometric data were compared with the theoretical spectra obtained by the density functional theory (DFT) method, showing a perfectmatch between them.UV-visible spectroscopy and steady-state fluorescence emission studies were performed for compound 7 in solvents of different polarities and the results were correlated with DFT calculations. Compound 7 showed a solvatochromism effect presenting higher molar extinction coefficient (log " = 4.57) and fluorescence quantum yield ( = 0.38) in toluene than in acetonitrile or methanol. The simulation of both frontier molecular orbitals (FMOs) and molecular electrostatic potential (MEP) suggested that the experimental spectra profile in toluene was not interfered by a possible charge transfer. These results are an indication of a low probability of compound 7 in reacting with unsaturated phospholipids in future applications as a fluorescent dye in biological systems.
ISSN: 1422-8599
DOI: 10.3390/M1276
Rights: openAccess
Appears in Collections:I&D CQC - Artigos em Revistas Internacionais

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