Control of helical chirality of poly(quinoxaline-2,3-diyl)s based on postpolymerization modification of the terminal group by small chiral molecules
Yuuya Nagata
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
Search for more papers by this authorSatoru Ohashi
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
Search for more papers by this authorCorresponding Author
Michinori Suginome
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
JST, CREST, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, JapanSearch for more papers by this authorYuuya Nagata
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
Search for more papers by this authorSatoru Ohashi
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
Search for more papers by this authorCorresponding Author
Michinori Suginome
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
JST, CREST, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, JapanSearch for more papers by this authorAbstract
Poly(quinoxaline-2,3-diyl)s having a terminal formyl or boronyl group were prepared by living polymerization of 1,2-diisocyanobenzenes using organopalladium initiators bearing a protected formyl or boronyl group. Poly(quinoxaline-2,3-diyl)s were successfully deracemized by reacting them with small optically active molecules at their terminal formyl or boronyl group, leading to the induction of optically active helical structures. Poly(quinoxaline-2,3-diyl) having terminal formyl groups was converted to one-handed helical polymer, in which the screw-sense excess was 68% (84:16). The helix sense of the boronyl-terminated poly(quinoxaline-2,3-diyl) was reversibly controlled by attaching and removing the chiral group. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012
Supporting Information
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| Filename | Description |
|---|---|
| POLA_25926_sm_suppinfo.pdf5.9 MB | Supporting Information 1 |
| POLA_25926_sm_suppinfo2.cif25 KB | Supporting Information 2 |
| POLA_25926_sm_suppinfo3.cif24.3 KB | Supporting Information 3 |
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