<i>C</i>₃‐Symmetrical Cyano‐Substituted Triphenylbenzenes for Organogels and Organic Nanoparticles with Controllable Fluorescence and Aggregation‐Induced Emission

Abstract

Abstract Fluorescent organic molecules with C 3 ‐symmetry consisting of tris{2‐cyano‐2‐[4‐(dodecyloxybenzoylamino)phenyl]‐1‐ethenyl}phenylbenzene (CN‐DBAPPBn, n = 1, 2, 3) were synthesized. It was observed that these compounds can spontaneously self‐assemble into organogels in many organic solvents. Scanning electron microscopy (SEM), light microscopy, and fluorescence microscopy images of the air‐dried gels showed the presence of either heavily entangled amorphous or fibrous structures, or rods. FTIR, UV/Vis absorption, excitation and emission spectra suggest that π–π interactions and H‐bonding are the driving forces for the formation of the gel phases. Moreover, spherical or cubic fluorescent nanoparticles based on CN‐DBAPPBn were prepared by using a reprecipitation method in a mixture of tetrahydrofuran and water. It is interesting that aggregation‐induced emission behavior of CN‐DBAPPBn was detected in both the gel phase and in the nanoparticle suspensions. The fluorescent molecular aggregates of CN‐DBAPPBn with different architectures and emission properties fabricated by using these self‐assembling methods could find potential applications in sensors and optoelectronic devices.