Quinoline based viologen as a multifunctional organic material – From crystal structures to photophysical and electrochemical properties, and application in DNA sensing and bioimaging

Developing new multifunctional organic materials is one of the current themes of research in organic materials chemistry. The class of N,N'-dialkylated bis-pyridinium compounds, namely, the viologens have been proven to offer such multifunctional materials. Herein, syntheses and crystal structure elucidation of trans-1,2-bis(4-quinolinyl)ethylene (BQE) and analogous N,N-dimethylated trans-1,2-bis(4′-quinolinium)ethylene (M2BQE) are discussed with their multifaceted materials properties. Two different crystal structures with significantly different molecular structures, namely, BQE and BQE⋅2H2O were obtained by tuning the solvent of crystallization. M2BQE showed a bathochromic shift both in its absorption (by ∼ 3300 cm−1) and in emission by (∼2900 cm−1) in compared to BQE, which is the effect of quaternization. Large Stokes shifts were observed for both the BQE (∼8500 cm−1) and M2BQE (∼8050 cm−1). Both compounds showed two-step reduction events in cyclic voltammetry, of which the first steps were reversible. The pH dependent absorption and emission properties of BQE have been explored which revealed the stronger effect by methylation than protonation. M2BQE exhibited selective binding to ct-DNA, as confirmed by selective quenching of emission intensity, over AMP and ATP. Furthermore, both the BQE and M2BQE displayed very intriguing features in bioimaging by intracellular co-localization in HeLa cells. While BQE is predominantly localizes in lysosomes over mitochondria, M2BQE dication, on the other hand, explicitly localizes in mitochondria.