Push-pull compounds exhibit unique spectroscopic properties which are attributed to an intramolecular charge transfer (ICT) from the electron donating (D) to the electron accepting group (A) separated by a π-linker. ICT generates a molecular dipole and polarization that imparts distinct electronic, linear and nonlinear optical (NLO) properties to the molecule with applications in telecommunications, optical data storage, optical switching, and high-performance computing. We synthesized a push-pull tetrazole substituted with a 4-(N,N-diphenylamino) phenyl group and p-nitrophenyl, pNPh2-tet-pNO2, by copper-catalyzed aerobic C-N coupling of p-nitrophenyl tetrazole with 4-(N,N-diphenylamino) phenylboronic acid. A blue shift is observed in the absorption and emission bands of pNPh2-tet-pNO2 with increasing solvent polarity. The compound also exhibits a strong solvent dependent emission with respect to both wavelength shift and intensity. Furthermore, it displays relatively weak fluorescence in polar solvents such as chloroform, acetonitrile and DMSO, and a remarkably strong emission in non-polar solvents, such as toluene. Currently, we are extending the investigation of the photophysical properties of pNPh2-tet-pNO2, in a series of aromatic solvents such as o-xylene, m-xylene, p-xylene, ethylbenzene, mesitylene, nitrobenzene, benzaldehyde, benzonitrile etc. to evaluate if the strong fluorescence is also manifested in other aromatic solvents.

Influence of aromatic solvents on the photophysical properties of push-pull tetrazoles

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