Synthesis of 2-aryl-5-styrylphospholes: promising candidates for the phosphole-based NLO chromophores.
2-Aryl-1-phenyl-5-styrylphospholes were prepared in good yields in a one-pot procedure from the corresponding 1,9-diarylnona-8-ene-1,6-diynes and dichloro(phenyl)phosphine via intermediary titanacyclopentadienes. According to the UV-vis absorption and fluorescence spectra of this class of compounds, the optical properties of the phosphole-vinylene-bridged pi-conjugated system have been revealed to depend strongly on the electronic character of the terminal functionalities. In particular, the polarizability at the excited-state has been found to be considerably greater than that in the ground state. High molecular hyperpolarizabilities obtained for the push-pull type of 2-aryl-5-styrylphospholes in the hyper-Rayleigh scattering measurements demonstrate the potential utility of the stilbene-type phosphole derivatives as a new class of second-order NLO chromophores.
Matano
Yoshihiro
Y
Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan. matano@sci.kyoto-u.ac.jp
Miyajima
Tooru
T
Imahori
Hiroshi
H
Kimura
Yoshifumi
Y