Configuration-controllable synthesis of Z/E isomers based on o-carborane-functionalized tetraphenylethene

Abstract

Z/E isomerism is a very important and interesting phenomenon in the field of chemistry. In many cases, people ignore the difference between Z/E isomers, and most studies investigate this hybrid system, thereby limiting the precise and in-depth understanding of the structure–performance relationship of materials. At present, only a few Z/E isomers of TPE derivatives can be separated, and the synthesis and separation of isomers modified by carborane substituents have not been reported. In this work, two Z/E isomers, namely, Z-TPE-2Car and E-TPE-2Car, with clear configuration were synthesized using an effective route. Both compounds have strong aggregation-induced luminescence (AIE) activity. The solid-state emission peaks of Z-TPE-2Car and E-TPE-2Car are 528 and 533 nm, respectively, and the emission peaks are shifted by 5 nm. The introduction of phenyl carborane substituents makes the two isomers have high solid-state fluorescence quantum yields, reaching 99% and 90%, respectively.