Effect of hydrogen bonding on the intramolecular charge transfer fluorescence of 6-dodecanoyl-2-dimethylaminonaphtalene

The effect of hydrogen bonding on the intramolecular charge transfer (ICT) of 6-dodecanoyl-2-dimethylaminonaphtalene (laurdan) in neat and binary solvent mixtures has been investigated by using steady-state and time-resolved spectroscopic techniques. The different features of ICT emission of laurdan in methylcyclohexane–tetrahydrofuran and methylcyclohexane–ethanol are explained by the absence and presence of hydrogen bonded ICT. The presence of isosbestic point in absorption spectra of laurdan in methylcyclohexane–ethanol confirms the formation of 1:1 complex between laurdan and ethanol. The obtained data were used to determine the stoichiometric equilibrium constants. In protic rigid (77 K) the fluorescence spectra of laurdan show excitation wavelength dependence (the red-edge effect). Moreover, we reported the decay characteristics of laurdan molecule in locally excited (LE) and ICT state in methylcyclohexane–ethanol.