Liquid-phase synthesis of block copolymers containing sequence-ordered segments.
Monodisperse sequence-defined oligomers have been synthesized in solution in the absence of protecting groups. These structures have been prepared stepwise using two consecutive chemoselective reactions: 1,3-dipolar cycloaddition of terminal alkynes and azides and amidification of carboxylic acids with primary amines. These oligomers were efficiently constructed on either a conventional solid support (commercial Wang resin) or tailor-made soluble polystyrene supports synthesized by atom-transfer radical polymerization. The latter approach was found to be very versatile. Indeed, well-defined soluble macromolecular supports allowed not only the synthesis and cleavage of defined oligomers (i.e., sacrificial support) but also the preparation of noncleavable block copolymers containing sequence-defined segments.
Pfeifer
Sebastian
S
Nanotechnology for Life Science Research Group, Fraunhofer Institute for Applied Polymer Research, Geiselbergstrasse 69, Potsdam-Golm 14476, Germany.
Zarafshani
Zoya
Z
Badi
Nezha
N
Lutz
Jean-François
JF
D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D011137:Polystyrenes / Q000737:chemistry; D012996:Solutions / Q000138:chemical synthesis / Q000737:chemistry
D000480:Alkynes; D000588:Amines; D001386:Azides; D002264:Carboxylic Acids; D011108:Polymers; D011137:Polystyrenes; D012996:Solutions