Enhanced solid state emission of quinoline derivatives for fluorescent sensors

Excited-state intramolecular proton transfer (ESIPT) molecules are of utmost interest in the fields of organic light emitting diode, photo-patterning, chemosensor, proton transfer laser, and photostabilizer. Fine control of the functional substituents as well as the molecular structure of core ESIPT unit is primarily demanded for specific applications. Here, the photophysics of quinoline derivatives of 2-quinolin-2-yl-phenol and 2-(8-chloroquinolin-2-yl)phenol is explored. Straightening the twist between the hydroxyphenyl and the quinoline moieties with the aid of the hydrogen bonding promoted the excited energy to flow through a radiative decay pathway via proton transfer to the nitrogen. Furthermore, close molecular packing of J-aggregates and thus resulted vibration restriction in a dense matter opens an ESIPT corridor and is characterized to show enhanced emission. The mechanism is applied to the selective Cu2+ or Fe2+ cation detection and further immunofluorescence labeling using avidin-biotin protein specific binding is demonstrated with the aid of nano self-assembly technique.