Extending Conjugation of Linear Cyanostilbene Derivatives via a Pyridine Moiety for Multi-Stimuli-Responsive Fluorescence Organogels.

In the design of effective gelators with aggregation-induced emission behavior, amide and cholesterol moieties are generally used to provide multiple driving forces for gelation. In this work, a series of linear cyanostilbene gelators with a pyridine moiety and different lengths of the alkoxyl group, i.e., CSpy-Cn, have been synthesized through nucleophilic substitution and Knoevenagel reaction. The direct connection of pyridine extends the conjugation of the cyanostilbene moiety, while the alkoxyl group can regulate the solubility of the compounds so that the compounds can serve as gelators for common solvents such as acetonitrile, dimethyl sulfoxide, and ethanol at ultra-low concentrations. At the same time, the cyanostilbene group makes the compounds undergo photoisomerization and emit fluorescence under UV light, while the pyridine group can serve as an acid-base responsive group due to easy protonation. The gels can respond to temperature, light, and organic acid/base. The fluorescence intensity and color can reversibly change during the gel-sol transitions. Finally, a thin film based on the CSpy-C8 xerogel has been prepared and utilized as a multi-stimuli-responsive fluorescence display for information storage and anti-counterfeiting.