A multifunctional Schiff base with aggregation-induced enhanced emission, gelation, and mechanochromic properties for anti-counterfeiting applications

Abstract

This work presents a systematic study of three closely related Schiff bases NpSB, AnSB, and PySB for their potential aggregation-induced enhanced emission, gelation, and mechanochromic properties. While aggregation-induced enhanced emission was observed in case of AnSB and PySB due to the suppression of photoinduced electron transfer; PySB also formed a stable gel in DMF‒water. Out of three Schiff bases, PySB exhibited reversible mechanochromism. Importantly, on applying pressure or a mechanical force, PySB changed its color from yellow to bright orange under the visible light while its emission wavelength shifted from 580 to 602 nm. More importantly, mechanical-force-induced changes were reversible after fuming with the vapors of CH2Cl2 or by heating at 100 °C. The mechanochromism of PySB was studied by a combination of powder X-ray diffraction, scanning electron microscope, differential scanning calorimetry, density functional theory, and nuclear magnetic resonance spectral studies. These studies concluded that the change in color and emission profile was due to change in the molecular packing of PySB after applying the pressure or mechanical force. The slippage of pyrene rings and the conversion of intramolecular H-bonding to intermolecular H-bonding resulted in the alteration of solid-state packing of PySB which was responsible for the mechanochromism. A noteworthy feature of the reversible mechanochromism of PySB was the reversible morphological changes as substantiated by the scanning electron microscope and powder X-ray diffraction studies. PySB was shown to illustrate noteworthy anti-counterfeiting and pressure-induced applications.