Crystal structure, Hirshfeld surface analysis and photophysical properties of disubstituted 4,4′-(benzo[c][1,2,5]thiadiazole-4,7-diyl)dianiline

Two independent molecules of the crystal structure of the title compound C18H14N4S were found to occupy the asymmetric unit of the space group. The flanking 4-anilines were not coplanar with the central benzothiadiazole, but they were twisted from the plane. In the crystal, two unique types of hydrogen bonds were found: i) one set between two NH2 of two molecules in the asymmetric unit and ii) another set between hydrogen atoms of the second aniline NH2 and the nitrogen atom of benzothiadiazole. The two-dimensional fingerprint plots along with the Hirshfeld surface confirmed the most important contributions for the crystal packing were C···H, H···H and N···H interactions. The compound was also solvatochromic with both its emission wavelength and quantum yield contingent on the solvent polarity. The fluorophore had a reversible oxidation. This was used to induce both a reversible color change from yellow to blue and emission off/on with an applied potential.