Modulation of excited state intramolecular proton transfer and intramolecular charge transfer pathways of symmetrical azines through micellar medium

Abstract

The photophysical studies of fluorescent probes in micellar medium can give a better insight about their interaction with biological membranes. This study attempts to access the photophysical properties of the dual emitting azine based probe diethylamino salicylidene azine dimer (DEASAD) in micellar media. DEASAD showed dual charge transfer emission due to the presence of open enol (480 nm) and closed enol (510 nm) forms in polar protic solvents. Upon increasing the concentration of ionic surfactants, there is a significant increase in the emission intensity of both the enol forms of DEASAD until premicellar concentration. After micellization, occurrence of a new anomalous keto form emission through excited state intramolecular proton transfer (ESIPT) was observed around 530 nm in ionic micelles and its intensity changes depend on the micellar surface charge. The emission studies revealed the position and interaction of DEASAD with the charge of micellar stern layer as confirmed through interaction of metal ion with the probe and control molecules with and without ESIPT and ICT moieties. In contrast, the new anomalous longer wavelength keto form of DEASAD emission was absent in neutral micelles like Triton X‐100.