Multi-stimuli responsiveness of pyrimidine bishydrazone: AIE, tuneable luminescence, white light emission, mechanochromism, acidochromism and its anticounterfeiting applications

The development of multifunctional properties associated with a single molecule being a centre of attention in the material science research area has been more focused in recent days. An aggregation-induced emissive (AIE) molecule having various aspects of stimuli-responsiveness such as mechanochromism, and acidochromism, along with white-light emitting behavior within a molecule will give rise to enormous applications in near future. A simple strategy to fabricate white-light emitting material from a single component system is beneficial for ap-plications in the field of flat-panel displays and other optoelectronic devices. Herein, we have designed a D-A-D triad-based AIE active organic molecule HYPY-DESAL via a facile one-step Schiff-base condensation reaction between 4,6-dihydrazinopyrimidine (HYPY) and 4-(N,N-diethylamino)salicylaldehyde (DESAL) containing ESIPT as well as ICT properties. This AIE-active molecule exhibits white light emission (fw approximate to 49%) feature in addition to the tunable emission characteristics in its aggregated states which can be utilized for various light emitting diode applications. The compound revealed exceptional solid-state stimuli responsiveness such as mechanofluorochromism and acidochromism. HYPY-DESAL exhibited acidochromic features with a remarkable red shift in emission wavelength greater than 150 nm in the solid state. The specific site of protonation upon TFA addition was confirmed via 1H NMR titration as well as TD-DFT experiments. The interesting reversible switching characteristics of the compound upon exposure to TFA/TEA are successfully utilized for several coding-decoding, information storage, and anti-counterfeiting applications in paper strips as well as PMMA-based thin films. Taken together, the combined features of the newly designed and readily accessible molecule exhibiting multi-stimuli responsive features such as AIE, tuneable luminescence, white light emission, mechanochromism, acid-ochromism, vapor phase sensing applicability using paper strips as well as thin films is unique, if not unprecedented.

Automated summary

The development of multifunctional properties associated with a single molecule has gained significant attention in recent material science research. An aggregation-induced emissive (AIE) molecule with stimuli-responsiveness such as mechanochromism, acidochromism, and white-light emitting behavior holds great potential for various applications. In this study, a D-A-D triad-based AIE active organic molecule HYPY-DESAL was designed through a facile one-step Schiff-base condensation reaction and demonstrated white light emission and tunable emission characteristics, making it suitable for light emitting diode applications. The molecule also exhibited exceptional solid-state stimuli responsiveness and was successfully used for coding-decoding, information storage, and anti-counterfeiting applications in paper strips and PMMA-based thin films. The combined features of this molecule, including AIE, tuneable luminescence, white light emission, mechanochromism, acidochromism, and vapor phase sensing, make it unique and potentially unprecedented.