Heterophenes revisited

Tien Yau Luh*, Hsin-Chieh Lin, Chih Ming Chou

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

By employing the furan annulation protocol, a new series of furan-containing teraryl [n.2]cyclophenes (n = 2-6 and 12) are prepared. These cyclophenes exhibit charge-transfer character in the absorption spectra and unusually large Stokes shifts in the emission spectra. They have neither particularly strong electron-donating moieties nor electron-withdrawing groups, but exhibit unusual second-order nonlinear optical (NLO) properties. The π-systems in teraryl system and in the bridging double bond are highly twisted. Interaction between these twisted π-systems may account for the significant enhancement in hyperpolarizability. Thiophene analog behaved similarly. The five-membered heteroaromatic rings may not only serve as electron donors, but also may accommodate the appropriate geometry to enable the interactions between the oligoaryl systems and the double bond leading to unusual photophysical and NLO properties.

Original languageEnglish
Pages (from-to)475-484
Number of pages10
JournalPure and Applied Chemistry
Volume80
Issue number3
DOIs
StatePublished - 1 Mar 2008

Keywords

  • Bridging double bond
  • Cyclophenes
  • Furan-containing oligoaryls
  • Nonlinear optical properties
  • Twisted π-system

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