Interaction of aromatic compounds and anions with naphthylimide-dansylamide fluorescent dyad: Experimental evidence of aryl C–H…π and aryl C–H…anion contacts and DFT calculations

Abstract

In this work the interaction of halide anions and simple aromatic compounds with a bichromophoric fluorescent dyad derived from 1,8-naphthalimide (NAPIM) and 5-(dimethylamino)naphthalene-1-sulfonyl (DANS) was studied using electronic spectroscopy, 1H, and 19F NMR spectroscopy and quantum chemistry modeling (b3lyp/def2-TZVP). The NAPIM-DANS dyad interacts with electron-rich guests with binding constants in the range of 6 x 10^3 to 8 x 10^3 M-1 in CHCl3. The formed complexes are stabilized through aryl C-H … anion and aryl C-H … pi interactions.