Synthesis and properties of tetraphenylethylene derivatives with different chiral substituents: From helical supermolecular structure to circularly polarized luminescence

Abstract

Two novel tetraphenylethylene derivatives (denoted as A12-TPE and T12-TPE) were prepared by incorporating different chiral d-gluconic acid substituents into the achiral TPE core. Their aggregation-induced emission (AIE) activity, self-assembly structure and circularly polarized luminescent (CPL) performance were then investigated using various techniques. The results reveal that both A12-TPE and T12-TPE exhibit AIE properties with quantum yields as high as 74.3% and 74.0% respectively. Moreover, due to the synergy effect of steric hindrance of the acetal group and chiral induction of d-gluconic acid, A12-TPE possesses a helical supermolecular structure, which endowed the material with distinct CPL properties. On the contrary, T12-TPE without the acetal group exhibits a lamellar structure rather than a helical structure, and no CPL signal can be observed. The helical supermolecular structure, in combination with the AIE activity and CPL performance of A12-TPE, make it a promising material for fabrication of chiral luminescent devices.