| Because of its special electronic system, [60] fullerene has strong electron accepting ability. And it can be used as electron acceptor (A) covalently linked with electron donor (D) to form a molecular D-A system. C60-Donor system can produce light-induced charge separation state, which plays an important role in the photoelectric conversion of organic solar cells, and the D-A molecules in the solar system can avoid the phase separation and cluster effects.In this paper, we designed and synthesized two [60] fullerene-Donor system 6 and 7 from the mother material of triphenylamine and through Kumada reaction, Vilsmeier-Haack reaction, Knoevenagel reaction and Prato reaction. The intermediates and the target products have been characterized and confirmed by IR, 1H-NMR, elemental analysis.Computational studies were performed using the density functional methods (DFT) at the B3LYP/3-21G(*) level with Gaussian 03 software package, The results shows that the majority of the electron density of the LUMO was found to be located on the C60 moiety, while the HOMO mainly concentrated in the substituents. Charge calculations show the C60 electron acceptor property and the electron donor property for the substituent. UV-vis absorption spectroscopy and fluorescence spectroscopy were used to study their optoelectronic properties, the UV absorption spectra of compound 7 shows broad absorb in the visible part; and the fluorescence spectra show that 6 and 7 both have the phenomenon of photoinduced charge transfer. Cyclic voltammetry were used for their electrochemical properties, the HOMO-LUMO gap of the compounds agreed with the band gap calculated by Gaussian 03 software package.
|
PDF Full Text Request