Abstract
Quaternary salts d-π-A+X- having a large π-conjugated system (I) 2-((Z)-1-cyano-2-[4-(dimethylaminophenyl]ethenyl)-1-methylpyridin-1-ium iodide, (II) 3-((Z)-1-cyano-2-[4-(dimethylaminophenyl]ethenyl)-1-methylpyridin-1-ium iodide, and (III) 4-((Z)-1-cyano-2 iodide -[4-(dimethylaminophenyl]ethenyl)-1-methylpyridin-1-ium iodide, were synthesized straightforwardly and easily and characterized by single-crystal X-ray diffraction, IR, UV–Vis, 1HNMR spectroscopy, DSC, and TGA. Quantum chemical calculations were performed to obtain electronic structure by using DFT. The salts I-III exhibited a hyperchromic shift and a strong bathochromic effect of 100 nm compared to the precursors, which indicates charge transfer (CT) due to ionic interactions. The Hirshfeld, MEPS, QTAIM, and NCI-RDG analyses showed that the -CN group and the counterion I(-) atom play major roles in the intermolecular interaction for crystal packing. The significance of non-covalent interactions for the stability of the molecules in their solid state is also revealed by natural bond orbital analysis.
Published Version
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