Halogenated Anils of Sulfanilamide: Structural, Hirshfeld, and Optical Studies

Abstract

Chemistry of functional organic materials is interesting in terms of design and applications. Halogen functionalization of organic molecules is intriguing as besides affecting the intramolecular electronic properties, their presence triggers intermolecular halogen bonds, affecting both packing and bulk properties. We report the rationally substituted halogenated anils of sulfanilamide 1–3 to understand the influence of halogens on molecular packing and bulk properties. The products 1 and 2 exhibit thermal stability beyond 300 ⁰C, whereas 3 undergoes early weight loss, indicating the presence of lattice solvent. The phase purity of the products has been confirmed with powder X‐ray analyses. Products have been further characterized through single‐crystal diffraction studies to understand crystal packing with further support from Hirshfeld studies. X⋯O interactions are predominant interactions and significant interhalogen X⋯X interactions are observed only in 2. The products are feebly emissive in solid‐state. Interestingly, 2 and 3 in thin film forms undergo emission quenching, whereas 1 exhibits augmented emission. AIE active anil 1 has been used for the sensing of explosive aromatic compound like picric acid.