Precise tuning of thermoresponsive property of poly(N-isopropylacrylamide)s by combination of ATRP and "click" chemistry

POLY 165

Ryohei Kakuchi, rk_ryohei@poly-bm.eng.hokudai.ac.jp1, Atsushi Toda, todai@poly-mc.eng.hokudai.ac.jp1, Atsushi Narumi, narumi@poly-bm.eng.hokudai.ac.jp1, Ryosuke Sakai, sakai@poly-mc.eng.hokudai.ac.jp1, Toshifumi Satoh, satoh@poly-mc.eng.hokudai.ac.jp1, Kenji Sugiyama2, Christopher W. Macosko3, Akira Hirao, ahirao@polymer.titech.ac.jp2, and Toyoji Kakuchi, kakuchi@poly-mc.eng.hokudai.ac.jp1. (1) Graduate School of Engineering, Hokkaido University, N13W8, Kita-ku, Sapporo 060-8628, Japan, (2) Polymeric and Organic Materials Department, Graduate School of Science and Technology, Tokyo Institute of Technology, H-127, 2-12-1, O-okayama, Meguro-ku, Tokyo, 152-8552, Japan, (3) Department of Chemical Engineering and Materials Science, The University of Minnesota, 421 Washington Avenue SE, Minneapolis, MN 55455
We prepared the ATRP initiator N-(2'-azidoethyl)-2-chloropropionyl amide (1), and the polymerization of NIPAM using the initiating system consisting of 1/CuCl/Me6TREN produced the end-functionalized PNIPAM with the azide group (2). We succeeded in introducing various substituents at the PNIPAM chain-end by the “click” reaction between 2 and various acetylenic compounds to afford the end-functionalized PNIPAM with the 4-phenoxyphenyl group, phenyl group, butyl group, octyl group, ethyl ester group, and hydroxyl methyl group. The aqueous solutions of the end-functionalized PNIPAM with hydrophobic groups showed lower LCSTs than that of 2. On the other hand, the LCST of end-functionalized PNIPAM with hydrophilic group was higher than that of 2. Thus, we showed that the combination of ATRP and the “click” chemistry was a convenient and facile strategy to precisely tune the thermo-responsive property of PNIPAM.
 

General Papers: Functional Materials
6:00 PM-8:00 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Polymer Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007