Abstract:
Prediction of multi-stimuli responsive behavior in newly developed luminogens is an appealing yet challenging puzzle, since no concrete design strategy has been developed so far. In this article, we demonstrate a potent strategy to gain a deep understanding of the structure–property relationship to design multi-stimuli responsive mechanochromic materials. To achieve our goal, a variety of new isoindolinone core based charge transfer luminogens exhibiting aggregation-induced emission (AIE) have been prepared through C–H bond activation using a cost-effective ruthenium (Ru) metal catalyzed one-pot synthetic strategy. We have shown that slight tuning of the donor moiety is found to be highly effective in controlling molecular packing and metastable energy states in solid states, and thus, optical properties and multi-stimuli responsive behaviors. The flexibility and twisting of donor moieties afford a loosely bound ‘herringbone’ packing, enabling reversible transformation under multiple mechanical stimuli. The cyclized derivative of the donor exhibits a completely different packing mode (i.e., cross packing), and subsequently, does not give rise to mechanochromism. The Hirshfeld surface analysis from a single crystal infers that non-covalent interactions (specifically C–H⋯π and π⋯π) are extremely important to yield mechanochromism under external force. Correlating all solid-state behavior with the molecular structure, we conclude that the synergistic effect between the twisting and conformational flexibility of donor moieties along with numerous non-covalent interactions gives rise to multi-stimuli responsive behaviors. Finally, the newly designed molecules are found to be highly emissive in solution and potentially applicable in fluorescence thermometer construction, lighting up cells, acid–base sensors and rewritable devices.