Abstract
The naphthalene is good contender which is intensively used in organic semiconductors. Here, three new naphthalene based compounds were prepared by the condensation of 1,5-diaminonaphthalene, 5-methylfurfural and 5-nitrofurfural. The prepared Schiff base compounds were analyzed by Fourier Transmission Infrared spectroscopy (FTIR), UV-vis spectroscopy (UV-vis) and single crystal x-ray studies. The compound 1 was obtained in P21/n crystal packing. A comprehensive electronic structure-property relationship was elucidated through the prism of frontier molecular orbitals (FM05). The calculated absorption wavelengths at TD-B3LYP/6-31G** level displayed reasonably decent agreement to the experimental data. The effect of electron donating groups and electron withdrawing groups was discussed on optoelectronic properties, ionization potentials, electron affinities and reorganization energies. On the basis of transfer integrals and intrinsic mobility nature of the charge transport of compound 1 was discussed. The electron injection, electronic coupling constant and light harvesting efficiency revealed that the studied Schiff base compounds would be good contestants to be used in dye-sensitized solar cells. Compounds 2 and 3 have 8 and 6 times larger beta(tot) than that of para-nitro aniline revealing that these materials might be good for nonlinear optics as well. (C) 2016 Elsevier GmbH. All rights reserved.