Synthesis and properties of DCDHF chromophore dimers

ORGN 54

Na Liu, nliu1@kent.edu1, Jeffrey A. Bertke, bertkeje@kent.edu1, Scott D. Bunge, sbunge@kent.edu1, Robert J. Twieg, rtwieg@lci.kent.edu1, Samuel J. Lord, sjlord@stanford.edu2, Jennifer Alyono, jalyono@stanford.edu2, and W. E. Moerner, wmoerner@stanford.edu2. (1) Department of Chemistry, Kent State University, Kent, OH 44242, (2) Department of Chemistry, Stanford University, Stanford, CA 94305-5080
Chromophores containing 2-dicyanomethylene-3-cyano-2, 5-dihydrofuran (DCDHF) have been developed for electrooptic and photorefractive applications and more recently have been exploited for their single-molecule fluorescence properties. Binding two DCDHF chromophores in the same molecule with a well-defined orientation can influence the absorbance, fluorescence emission, quantum yield and other photophysical properties compared with the mono-DCDHF counterpart. The synthesis and photophysical properties of novel DCDHF chromophore dimers with a 1,4-cyclohexane spacer are presented here. X-ray analysis shows that the two chromophores in the trans dimer are parallel to each other and the cyclohexane ring prefers to stay in a chair conformation. Different fluorescence characteristics were found for the dimers compared to the mono-DCDHF counterpart. For example, the trans dimer shows significantly higher fluorescence quantum yield in solution.

 

Materials, Devices, and Switches
8:00 AM-12:00 PM, Sunday, 10 September 2006 Moscone Center -- Room 132, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006