Open AccessDevelopment of Imidazole-Reactive Molecules Leading to a New Aggregation-Induced Emission Fluorophore Based on the Cinnamic Scaffold
Author(s) -
Vincenzo Razzano,
Marco Paolino,
Annalisa Reale,
Germano Giuliani,
Roberto Artusi,
Gianfranco Caselli,
Michela Visintin,
Francesco Makovec,
Alessandro Donati,
Francesca Monteleone,
Chiara Botta,
Andrea Cappelli
Publication year - 2017
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.7b00789
Subject(s) - fluorophore , imidazole , intramolecular force , chemistry , molecule , fluorescence , photochemistry , scaffold , indole test , combinatorial chemistry , stereochemistry , organic chemistry , medicine , physics , quantum mechanics , biomedical engineering
In order to obtain new fluorophores potentially useful in imidazole labeling and subsequent conjugation, a small series of Morita-Baylis-Hillman acetates ( 3a-c ) was designed, synthesized, and reacted with imidazole. The optical properties of the corresponding imidazole derivatives 4a-c were analyzed both in solution and in the solid state. Although the solutions display a very weak emission, the powders show a blue emission, particularly enhanced in the case of compound 4c possessing two methoxy groups in the cinnamic scaffold. The photophysical study confirmed the hypothesis that the molecular rigidity of the solid state enhances the emission properties of these compounds by triggering the restriction of intramolecular motions, paving the way for their applications in fluorogenic labeling.