Development of Imidazole-Reactive Molecules Leading to a New Aggregation-Induced Emission Fluorophore Based on the Cinnamic Scaffold

In order to obtain new fluorophores potentially useful in imidazole labeling and subsequent conjugation, a small series of MoritaBaylis-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.