Side chain effects on the solid-state emission behaviours and mechano-fluorochromic activities of 10H-phenothiazinylbenzo[d]imidazoles

A family of 4-cyanophenyl-substituted 10H-phenothiazinylbenzo[d]imidazoles with different side chains at the 10-position are prepared and their physical properties are studied. The detailed structure-property research demonstrates that the cold crystallization temperature of ground samples and the emission wavelengths of pristine samples are in good accordance with the packing density, conformation distortion and intermolecular interactions, but emission wavelengths of ground samples are slightly chain-dependent. For benzimidazoles with alkyl chains, longer and more branched chains can produce looser packings, which cause pristine samples to display red-shifted emission and reduced MFC activity. For benzimidazoles with a phenyl chain, the emission wavelengths of both the pristine and the ground samples are remarkably red-shifted. Moreover, the degree of conformation distortion is larger, and the cold crystallization temperature is higher. Interestingly, the homologue with the n-hexyl chain displays an intense ML effect that is mainly attributed to the heavy discharge quantity on largely enhanced discharge areas under force stimuli due to the great fragility of this crystal.