Observing second-order nonlinear optical properties by symmetry breaking in centrosymmetric furan-containing oligoaryl cyclophandienes.
Centrosymmetric furan-containing cyclophandienes 3 and 4, synthesized by our furan annulation protocol, have been shown to exhibit extraordinarily large Stokes shifts and second-order nonlinear optical beta values. The beta values for 3 and 4 measured at 1.32 mum are 208 and 530x10(-30) esu, respectively. The beta values of 3 and 4 are similar to those of respective cyclophenes 1 a and 7 in which strong hyperpoarizable interactions between two twisted pi-systems (oligoaryl and bridging double bond) might take place. Symmetry breaking due to the resonance contribution (cf. 2) and the unique structural features of 3 and 4 has been used to account for this unusual photophysical behavior.
Lin
Hsin-Chieh
HC
Department of Chemistry, National Taiwan University, Taipei 106, Taiwan.
Hsu
Jui-Hung
JH
Lee
Chao-Kuei
CK
Tai
Oliver Yung-Hui
OY
Wang
Chin-Hsien
CH
Chou
Chih-Ming
CM
Chen
Kuang-Yen
KY
Wu
Yi-Lin
YL
Luh
Tien-Yau
TY