Structures, photoresponse properties and DNA binding abilities of 4-(4-pyridinyl)-2-pyridone salts

Abstract

Three salts [perchlorate (2), chloride (3) and tetrafluoroborate (4)] were synthesized from a 1-(2-aminoethyl)-6-hydroxy-2-oxo-1,2-dihydro-[4,4′-bipyridine]-3,5-dicarbonitrile compound (1) and characterized by spectroscopic and single crystal X-ray diffraction methods. Various noncovalent interactions (e.g., anion⋯π⁺, π⋯π, lp⋯π) are explored in the solid state crystal structure of the salts. Optical band gaps of all the four compounds were determined from their solid-state UV-vis spectrum. Electrical properties like electrical conductivity, photosensitivity, etc. were calculated and the results revealed that they have potential to act as optoelectronic devices. The values of the electrical parameters increase several times when they are exposed to visible light rather than in dark conditions. The light sensing properties of the salts (2–4) are enhanced compared to that of the mother organic compound 1 but the magnitude of this enhancement is not same for the three salts. This observation has been rationalized by theoretical considerations. Moreover, the DNA binding ability of one of the representative salts (compound 2) was examined to check the biological importance of the synthesized salts.