To get insight on
how the donor (D)/acceptor (A) substitutions
and their substitution pattern affect optical properties in solution
and in the solid state, four novel carbazole derivatives C1–C4 with different terminal groups (N(CH3)2, H, Br, and CN) have been employed. Their single-crystal
X-ray structures confirm that the twisted structures, intermolecular
interactions, and loose molecular packing are functions of the terminal
groups. Interestingly, they displayed substituent-dependent aggregation-induced
behaviors and mechanochromic (MC) properties. C1 showed
aggregation-caused quenching because of the strong intermolecular
π–π interaction, whereas C2, C3, and C4 exhibit strong aggregation-enhanced
emission characteristics, which contributed to the formation of J-aggregates.
Different twisted conformations and molecular arrangements induce
different mechanostimuli response behaviors for C1–C4 between green-yellow to red color along with large red-shifts
of 63, 30, 56, and 49 nm, respectively. C1, C3, and C4 displayed obvious MC characteristics, but C2 displayed irreversible mechanostimulus behavior. Powder
X-ray diffraction and single-crystal X-ray analysis revealed that
planarization of the twisted structure extended the π-conjugation
and the destruction of the crystalline structure accounted for the
tuned solid-state fluorescence.