Synthesis, photophysical characterization, aggregation-induced emission effect and crystal structure of (E)-butyl-3,3'-(5,6-dicarbazolylbenzo[c][1,2,5]thiadiazolyl)acrylate

Abstract

In this study, we report the development of a simple and highly efficient synthetic protocol for the preparation of novel (E)-butyl-3,3'-(5,6-dicarbazolylbenzo[c][1,2,5]thiadiazolyl)acrylate via Heck cross-coupling reactions catalyzed by palladium. Optimized conditions utilizing a Pd(OAc)₂/K₂CO₃ system afforded high yields (70%), resulting in the successful synthesis and characterization (¹H-NMR, ¹³C-NMR) of a new compound. Detailed investigations into its photophysical properties revealed pronounced aggregation-induced emission (AIE) behavior. Single-crystal X-ray diffraction analysis provided insights into the molecular packing and structure–property relationships, while computational chemistry supported the understanding of its electronic features. This work presents a valuable contribution to the field of C–C cross-coupling chemistry, offering a practical and versatile approach for the synthesis of diverse 4,7-dialkylated-5,6-N,N-dicarbazolylbenzothiadiazole derivatives, with potential applications in medicinal chemistry and materials science.