Characterization of Push-Pull-Type Benzo[X]quinoline Derivatives (X = g or f): Environmentally Responsive Fluorescent Dyes with Multiple Functions.
J Org Chem
; 85(20): 13177-13190, 2020 10 16.
Article
em En
| MEDLINE
| ID: mdl-32940474
ABSTRACT
Benzo[X]quinoline (X = g or f BQX) derivatives bearing bis-trifluoromethyl and amine groups have been designed as push-pull-type fluorescent dyes. Through the synthesis of BQX derivatives from 2,7-diaminonaphthalene, linear-type (BQL) and angular-type (BQA) structural isomers were obtained. X-ray structures of single crystals from six given BQX derivatives revealed that the BQL and BQA series adopt planar- and bowl-shaped structures. In the fluorescence spectra, interestingly, the BQL series emitted in the near-infrared region over 700 nm in polar solvents. Based on the visible absorptions and base properties related to the amine moiety, the ammonia responsiveness was investigated using an ion-exchange reaction by the BQX-HCl salt. By exploiting the environmentally responsive fluorescence probe, cell imaging through confocal laser microscopy was conducted using HeLa and 3T3-L1 cells, emitting specific lipid droplets. The results indicate that BQX derivatives have multiple functions and may be applied in materials chemistry and biochemistry.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Quinolinas
/
Corantes Fluorescentes
Limite:
Humans
Idioma:
En
Ano de publicação:
2020
Tipo de documento:
Article