Synthesis, photophysical properties and aggregation-induced enhanced emission of bischalcone-benzothiadiazole and chalcone-benzothiadiazole hybrids

Autor(es)

Martins da Costa, Rafaela Gomes ^[1] ; Garcia, Rafael de Queiroz ^[2] ; Fiuza, Raquel Mazzoli da R. ^[1] ; Maqueira, Luis ^[1] ; Pazini, Alessandra ^[1] ; de Boni, Leonardo ^[2] ; Limberger, Jones ^[1]

Afiliação do(s) autor(es)

^[1] Pontifical Catholic Univ Rio de Janeiro, Dept Chem, Rua Marques de Sao Vicente 225, BR-22451900 Rio De Janeiro, RJ - Brazil

^[2] Univ Sao Paulo, Sao Carlos Inst Phys, Phys & Mat Sci Dept, Ave Trabalhador Sancarlense, Sao Carlos, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of Luminescence; v. 239, NOV 2021.
• Citações Web of Science: 0

Resumo

Hybrids containing both chalcone and benzothiadiazole (BTD) moieties were synthesized and photophysically characterized. The compounds display either chalcone-BTD-chalcone or aryloxy-BTD-chalcone architectures. The synthesis of these dyes was based on aldol condensations in formyl-substituted BTD-based intermediates. The hybrids presented absorption maxima ranging from 384 to 408 nm with remarkably high extinction coefficient values (1.31-4.04 x 10(4) L mol(-1) cm(-1)). Regarding the emission, all compounds are fluorescent in solution with emission maxima ranging from 481 to 535 nm and Stokes shifts between 81 and 148 nm. The quantum yields of fluorescence (phi(f)) ranged from 0.002 to 0.40 in solution and they were dependent on the architecture of the hybrids as well as the substitution pattern of the chalcone aryl group. In respect to aggregation-induced enhanced emission properties, while the fluorescence of bischalcone-BTD hybrids was not increased by aggregation, the compound with design aryloxy-BTD-chalcone presented AIEEgen properties since a sharp increase (30-fold) in the fluorescence intensity along with a remarkable enhancement of phi(f) values (from 0.0070 to 0.143) were observed upon aggregation. (AU)

• Processo FAPESP: 18/03758-5 - Montagem de uma linha experimental de espectroscopia de plasma induzido por laser (LIBS) com pulsos de femtossegundos
• Beneficiário: Rafael de Queiroz Garcia
• Modalidade de apoio: Bolsas no Brasil - Iniciação Científica
• Processo FAPESP: 16/20886-1 - Modernização da linha de Espectroscopia Óptica Não Linear ultrarrápida: Absorção transiente e chave kerr óptica com controle da polarização.
• Beneficiário: Leonardo de Boni
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 20/16036-8 - Espectroscopia ultrarrápida: excitação e prova degenerados e não degenerados resolvidos em polarização
• Beneficiário: Rafael de Queiroz Garcia
• Modalidade de apoio: Bolsas no Brasil - Mestrado