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Entering a New Level of Use for Suzuki Cross‐Coupling: Poly( para ‐phenylene)s with Fourth‐Generation Dendrons
Author(s) -
Bo Zhishan,
Schlüter A. Dieter
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20000901)6:17<3235::aid-chem3235>3.0.co;2-4
Subject(s) - monomer , condensation polymer , suzuki reaction , phenylene , polymer chemistry , dendrimer , polystyrene , polymer , materials science , chemistry , organic chemistry , alkyl , aryl
Three different synthetic routes to the fourth‐generation (G4) macromonomers 4, 6 , and 9 for Suzuki polycondensation (SPC) are described and compared in their efficiency. Monomer 9 was selected the best as judged by the number and feasibility of synthetic steps and purification behavior and could be prepared in a 15 g scale. SPC of the monomers 4, 6 , and 9 gave the novel poly( para ‐phenylene)s 17, 18 , and 19 with pendant G4 dendrons at every other repeat unit. SPC was optimized for 9 and the diboronic acid ester counterpart 16 which led to polymer 19 with a molecular weight of up to M n =76 000, M w =639 000 (GPC versus polystyrene). High molecular weight is most likely to be obtained for the attempted stoichiometry 9 : 16 =1.000:(0.995–1.005).