Observing second-order nonlinear optical properties by symmetry breaking in centrosymmetric furan-containing oligoaryl cyclophandienes

Hsin Chieh Lin, Jui Hung Hsu*, Chao Kuei Lee, Oliver Yung Hui Tai, Chin Hsien Wang, Chih Ming Chou, Kuang Yen Chen, Yi Lin Wu, Tien Yau Luh

*Corresponding author for this work

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

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 β values. The β values for 3 and 4 measured at 1.32 mm are 208 and 530 × 10 -30 esu, respectively. The β values of 3 and 4 are similar to those of respective cyclophenes 1a and 7 in which strong hyperpoarizable interactions between two twisted π-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.

Original languageEnglish (US)
Pages (from-to)13201-13209
Number of pages9
JournalChemistry - A European Journal
Volume15
Issue number47
DOIs
StatePublished - Dec 7 2009

Keywords

  • Cyclophandienes
  • Nonlinear optics
  • Oligoaryls
  • Photochemistry
  • Symmetry breaking

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Observing second-order nonlinear optical properties by symmetry breaking in centrosymmetric furan-containing oligoaryl cyclophandienes'. Together they form a unique fingerprint.

  • Cite this

    Lin, H. C., Hsu, J. H., Lee, C. K., Tai, O. Y. H., Wang, C. H., Chou, C. M., Chen, K. Y., Wu, Y. L., & Luh, T. Y. (2009). Observing second-order nonlinear optical properties by symmetry breaking in centrosymmetric furan-containing oligoaryl cyclophandienes. Chemistry - A European Journal, 15(47), 13201-13209. https://doi.org/10.1002/chem.200902115