Photophysical behaviour of 1-(4-N, N-dimethylaminophenylethynyl)pyrene (DMAPEPy) in homogeneous media

The photophysical behaviour of a new pyrene derivative, 1-(4-N, N-dimethylaminophenylethynyl)pyrene (DMAPEPy), in various solvents has been studied. Due to the presence of an ethynyl link with a cylindrical π cloud between the donor (N, N-dimethyl group) and the acceptor (pyrene), the molecule shows efficient intramolecular charge transfer, with a high extinction coefficient in all the solvents. There is significant solvatochromism in the fluorescence with a large increase in the Stokes’ shift of around 125 nm between n-hexane and acetonitrile. The solvent-dependent spectral data show a good correlation with the Kamlet–Taft solvent polarity parameter (π*). The plots of Stokes’ shifts with ET(30) are linear for non-protic solvents and for protic solvents but with different slopes. The fluorescence quantum yields are high for non-polar solvents and decrease as the solvent polarity increases. Unlike the parent molecule pyrene, DMAPEPy shows a short lifetime, which is fairly insensitive to oxygen-induced quenching and is dependent on solvent polarity. The molecule shows high steady-state fluorescence anisotropy, which is very sensitive to the viscosity change of the medium. © 2006 The Royal Society of Chemistry and Owner Societies.