Highly fluorescent and completely water-soluble poly(p-phenyleneethynylene) copolymer for bioconjugation

POLY 94

Kangwon Lee, kangwonl@umich.edu1, Jae Cheol Cho1, Jennifer DeHeck, jid@umich.edu2, and Jinsang Kim, jinsang@umich.edu1. (1) Department of Materials Science and Engineering, University of Michigan, Ann Arbor, MI 48109, (2) Chemical Engineering, University of Michigan, 3074 H. H. Dow Building 2300 Hayward St., Ann Arbor, MI 48109-2136
We describe the synthesis and functionalization of a completely water-soluble conjugated polymer, poly{[1,4-bis(1,3-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)propan-2-yloxy) benzene]-alt-[2,5-diethynylbenzene-2,4-(bis(3-propoxy-sulfonic acid))sodium salt]} (PPE-R1), to improve the emissive property even futher and give bioconjugation capability. The copolymer, PPE-R1, is composed of alternating ionic sulfonate units and bifurcated non-ionic ethylene oxide units on the main chain to provide water solubility and prevent micelle formation. The conventional palladium-catalyzed Sonogashira-Hagihara copolymerization was used. We developed a method to introduce a carboxylic acid group, a versatile functional group for bioconjugation, at the end of PPE chain. The chemically modified polymer with a carboxylic acid group at both ends of the polymer was subsequently conjugated with a model peptide, pentatyrosine molecules.
 

General Papers: Polymers and Biology
6:00 PM-8:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Division of Polymer Chemistry

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