US EPA

6929769 

Journal Article 

Synthesis of Bis(styryl) benzene Derivatives of Typical A-A-A Conjugation Structure with Large Two-photon Absorption Cross Sections 

Huang Chi-Bao; Ren An-Xiang; Li Hai-Bo; Yang Nian-Fa; , 

2010 

1 

Gaodeng Xuexiao Huaxue Xuebao / Chemical Journal of Chinese Universities
ISSN: 0251-0790 

HIGHER EDUCATION PRESS 

BEIJING 

2222-2227 

WOS:000285538100021 

The synthesis of FR[2,5-dicyano-1,4-bis-(4'-fluorostyryl) benzene] with typical A-A-A conjugation structure was reported, and its structure was characterized by H-1 NMR, IR and elemental analysis. One- and two-photon absorption and emission properties of bis(styryl) benzene derivatives including FR and CY[2,5-dicyano-1,4-bis-(4'-cyanostyryl) benzene] with A-A-A conjugation structure, and MO[2,5-dicyano-1,4-bis-(4'-methoxystyryl) benzene] and MA[2,5-dicyano-1,4-bis-(4'-dimethylaminostyryl) benzene] with D-A-D conjugation structure were studied by the one- and two-photon-induced fluorescence emission in femtosecond pulses, respectively. The maximum wavelengths of the one-photon absorption and emission increased with increasing electron-donating capacity of terminal substituent groups, and compounds FR and CY of electron-accepting terminal groups displayed very high fluorescence quantum yields (0.92 and 0.89, respectively), long fluorescence lifetime (5.8 and 6.1 ns, respectively) and large two-photon absorption coefficient (19.1 and 20.5, respectively). The two-photon absorption cross sections (delta) of FR and CY(6350 GM and 6870 GM, respectively) with strongly electron-accepting terminal groups were much larger than those of MO and MA (270 GM and 1790 GM, respectively) with electron-donating terminal groups. The result indicates that bis(styryl) benzene derivatives with A-A-A conjugation structure exhibit a considerably large delta.