Phenanthrene-tethered furan-containing cyclophenes: Synthesis and photophysical properties

Hao Tien Bai, Hsin-Chieh Lin, Tien Yau Luh*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

(Figure presented) Two phenanthrene-fused furan-containing teraryl cyclophenes 5 and 6 are synthesized. These cyclophenes exhibit charge transfer band in the absorption spectra, unusually large Stokes shifts in the emission spectra, and exceptionally high μβ values in the electric-field-induced second-harmonic generation (EFISH) experiments. The μβ1.91 values for 5 and 6 are 438 and 777 × 10-48 esu, respectively. The bridging double bond in 5 and 6 can serve as either an electron donor or acceptor depending on the nature of the substituent on furan rings. DFT calculations at the B3LYP/6-31G* level indicate that the electron density distributions in HOMO and LUMO are very different. Interaction between the oligoaryl systems and the double bond may account for the significant enhancement in hyperpolarizability.

Original languageEnglish
Pages (from-to)4591-4595
Number of pages5
JournalJournal of Organic Chemistry
Volume75
Issue number13
DOIs
StatePublished - 2 Jul 2010

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