Acta Phys. -Chim. Sin. ›› 2009, Vol. 25 ›› Issue (07): 1320-1326.doi: 10.3866/PKU.WHXB20090718

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Synthesis, Two-Photon Properties and Electrochemistry of A-B2 Type Nitro-stilbene Dyes with Benzophenone Groups

GAO Fang, HU Nv-Dan, WANG Jian-Chao, YANG Liu-Feng, YANG Long, LI Hong-Ru, ZHANG Sheng-Tao   

  1. College of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, P. R. China
  • Received:2009-03-09 Revised:2009-03-31 Published:2009-06-26
  • Contact: GAO Fang, LI Hong-Ru;


We discuss the synthesis and characterization of 3',4'-bis(p-benzoylphenylmethoxy)yl-4-nitrostilbene (C1). Ultraviolet and fluorescence spectroscopy was used to investigate its behavior in various solvents. Results showed that the visible absorption of C1 could be assigned to the chromophore and that the attached benzophenone made major contribution to the ultraviolet absorption of C1. This compound exhibited strong fluorescence in modest polar solvents.Acomprehensive investigation of the two-photon properties and electrochemistry of C1 and 2',4'-bis(p-benzoylphenylmethoxy)yl-4-nitrostilbene (C2) was undertaken. Results suggested that at 800 nm femtosecond laser excitation, C1 and C2 showed strong two-photon induced upconversion fluorescence. The two-photon absorption cross-section of the compound was shown to be related to the substitution position of benzophenone. Molecular geometry optimization and electrochemistry suggested that the energies of the frontier orbitals and electron densities of C1 and C2 could be correlated to the position of benzophenone substitution as well.

Key words: Stilbene derivative, Synthesis, Two-photon absorption, Electrochemistry, Molecular geometry optimization