Donor - Acceptor thiolated polyenic chromophores exhibiting large optical nonlinearity and excellent photostability

Yen-Ju Cheng, Jingdong Luo, Su Huang, Xinghua Zhou, Zhengwei Shi, Tae Dong Kim, Denise H. Bale, Satsuki Takahashi, Andrew Yick, Brent M. Polishak, Sei Hum Jang, Larry R. Dalton, Philip J. Reid, William H. Steier, Alex K.Y. Jen

Research output: Contribution to journalArticlepeer-review

136 Scopus citations

Abstract

We have successfully utilized epoxyisophorone ring-opening chemistry to efficiently incorporate the butylthio group to the phenyltetraene bridge of highly efficient nonlinear optical chromophores in high overall yield. By following the guidance of Dewar's rules, the sulfur atom functions as a moderate π-accepting group at a starred position of the conjugated bridge. Several of very critical material parameters of the phenyltetraenic chromophores for device applications have been intrinsically and simultaneously improved through such a simple and straightforward engineering of molecular structures. Compared with the nonsubstituted analogue 2, thiolated chromophore 1 achieves higher molecular hyperpolarizability (34%), enhanced E-O coefficient (38%), significantly improved photochemical stability against 1O2 (by an order of magnitude), and better optical transparency (17 nm blue-shifted λmax absorption spectrum).

Original languageEnglish
Pages (from-to)5047-5054
Number of pages8
JournalChemistry of Materials
Volume20
Issue number15
DOIs
StatePublished - 12 Aug 2008

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