Synthesis, experimental and theoretical photophysical study of proton transfer based oxazoline fluorophores. Potential tailor made optical sensors for enantiomeric detection in solution

Autor(es)

Santos, Fabiano S. ^[1] ; Zanotto, Gabriel M. ^[2] ; Argomedo, Luis M. Z. ^[3] ; Darbem, Mariana P. ^[3] ; Goncalves, Paulo F. B. ^[2] ; Stefani, Helio A. ^[3] ; Rodembusch, Fabiano S. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Fed Rio Grande do Sul, Grp Pesquisa Fotoquim Organ Aplicada, Inst Quim, Av Bento Goncalves 9500, BR-91501970 Porto Alegre, RS - Brazil

^[2] Univ Fed Rio Grande do Sul, Grp Quim Teor, Inst Quim, Av Bento Goncalves 9500, BR-91501970 Porto Alegre, RS - Brazil

^[3] Univ Sao Paulo, Fac Ciencias Farmaceut, Av Prof Lineu Prestes 580, Bloco 13 Super, BR-05508900 Sao Paulo, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: DYES AND PIGMENTS; v. 165, p. 372-382, JUN 2019.
• Citações Web of Science: 0

Resumo

A series of oxazoline based compounds was obtained via amidation formation from salicylic acid derivatives and benzyl-protected L-threonine with good yields (50-90%). These compounds present absorption in the UV region (similar to 300 nm) and fluorescence emission spectra show large Stokes shift emission (similar to 10000 cm(-1)) in the bluegreen region attributed to the ESIPT process. TD-DFT calculations were carried out to investigate the process of proton transfer of the structure of both tautomers (keto and enol) and corroborating the UV region absorption and large Stokes shift. The oxazolines derivatives were investigated as optical sensor for enantiomeric identification in solution. Preliminary results indicate sensing for arabinose and tartaric acid, but not specificity. However, to the pair R-(-)-Mandelic and S-(+)-Mandelic acid, the oxazoline 4c showed a enantiomeric selectivity identification, allowing to envisage these compounds as potential photoactive building blocks to propose innovative optical sensors in solution. (AU)

• Processo FAPESP: 16/24396-9 - 2-Ariloxazolinas triazólicas: síntese de pequenas bibliotecas, atividade biológica, fluorescência e ligantes
• Beneficiário: Mariana Pompilio Darbem Rocha
• Modalidade de apoio: Bolsas no Brasil - Doutorado
• Processo FAPESP: 17/24821-4 - Reações de Acoplamento Carbonilativo e Cicloadição [2+2] Intramolecular Empregando D-Glucal
• Beneficiário: Helio Alexandre Stefani
• Modalidade de apoio: Auxílio à Pesquisa - Regular