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(Referência obtida automaticamente do Web of Science, por meio da informação sobre o financiamento pela FAPESP e o número do processo correspondente, incluída na publicação pelos autores.)

Thiocyanation of 3-substituted and 3,5-disubstituted BODIPYs and its application for the synthesis of new fluorescent sensors

Texto completo
Autor(es):
Rezende, Lucas C. D. [1] ; Melo, Shaiani M. G. [2] ; Boodts, Stijn [3] ; Verbelen, Bram [3] ; Emery, Flavio S. ; Dehaen, Wim [3]
Número total de Autores: 6
Afiliação do(s) autor(es):
[1] Univ Fed Espirito Santo, Ctr Univ Norte Espirito Santo, Dept Ciencias Nat, Sao Mateus, ES - Brazil
[2] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, Dept Ciencias Farmaceut, Ribeirao Preto, SP - Brazil
[3] Katholieke Univ Leuven, Dept Chem, Celestijnenlaan 200F, B-3001 Leuven - Belgium
Número total de Afiliações: 3
Tipo de documento: Artigo Científico
Fonte: DYES AND PIGMENTS; v. 154, p. 155-163, JUL 2018.
Citações Web of Science: 7
Resumo

Interest in BODIPYs (acronym of boron dipyrromethene) has skyrocketed in recent decades, mainly due to their favourable photophysical properties and the wide range of functionalization methods reported for these organic fluorescent dyes. In this context, a simple and straightforward method for the direct thiocyanation of 1,3,5,7-tetramethy-BODIPYs using ammonium thiocyanate and oxone was recently reported as an alternative for the preparation of thiocyanated and thioalkylated BODIPYs. Herein, we performed the thiocyanation of 3-substituted and 3,5-disubstituted BODIPY dyes, which were synthesized from the nucleophilic substitution of halogenated precursors with morpholine, propanethiol and sodium methoxide. There was a direct relation between the electron-donating character of the substituent and the yields of the thiocyanated BODIPYs, which gives support to a mechanism based on the electrophilic substitution by a thiocyanogen species formed in situ. Spectroscopic and photophysical characterization of these new fluorophores was performed and included bidimensional NMR, UV/vis absorption, fluorescence emission and fluorescence quantum yields. The photophysical properties are highly dependable on the structural features of each dye. While 3-morpholino-8-phenyl BODIPYs are virtually non-fluorescent, the fluorescence quantum yields of 3-(4-methoxybenzylamino)-8-methyl BODIPYs were close to 0.9. The thiocyanation of BODIPYs can result in interesting photophysical shifts that can be explored in the fine-tuning of fluorescent sensors. We also report the results of a preliminary qualitative analysis that indicates interesting bathochromic or hypsochromic shifts on the absorption and fluorescence emission spectra when some of the highly emissive dyes were treated with strong acid. (AU)

Processo FAPESP: 14/18973-8 - Aplicação da química de sais de diazônio na modificação estrutural de fluoróforos do tipo BODIPY
Beneficiário:Shaiani Maria Gil de Melo
Linha de fomento: Bolsas no Brasil - Mestrado
Processo FAPESP: 14/22451-7 - Sistemas de liberação sustentada e direcionada de fármacos para o tecido epitelial
Beneficiário:Renata Fonseca Vianna Lopez
Linha de fomento: Auxílio à Pesquisa - Temático
Processo FAPESP: 11/23342-9 - Síntese,caracterização e aplicações de fluoróforos derivados do BODIPY.
Beneficiário:Lucas Cunha Dias de Rezende
Linha de fomento: Bolsas no Brasil - Doutorado