Abstract
Two cyanostyrylanthracene derivatives linked with N-dodecyl-l-phenylalaninamide by succinyl (PC2AN) and glutaryl (PC3AN) groups were successfully synthesized. The self-assembly and mechanofluorochromism (MFC) were investigated. Results showed the presence of cyano groups induced two compounds emitted weak fluorescence in solution and possessed strong fluorescence in the aggregated state, exhibiting typical aggregation-induced emission. The two compounds formed gels in certain solvents and also exhibited gelation-induced emission enhancement. The circular dichroism spectra of the gels suggested that chromophores of two gelators in gel phases were stacked into chiral aggregates. Moreover, PC3AN possessed better gel abilities than PC2AN. The gel-to-sol phase transition temperatures (Tgel) of PC2AN are higher than those of PC3AN in o-dichlorobenzene under the same concentrations. UVâvisible absorption and infrared spectra showed that the hydrogen bonding between aromatic amide groups and the ÏâÏ interaction in the PC3AN gel are stronger than those in the PC2AN gel. Solid PC3AN did not change its emission color after applying mechanical force. Interestingly, PC2AN exhibited significant MFC. The PC2AN emitted blue-green fluorescence, which turned into yellow upon grinding. Thus, only one methylene group has significant effects on gelation ability and MFC.
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