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Anionic synthesis and characterization of ω‐formyl‐functionalized polystyrenes
Author(s) -
Quirk Roderic P.,
Kuang Jianxin
Publication year - 1994
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.1994.210330209
Subject(s) - titration , alkoxide , hydroxylamine , methanol , polymer chemistry , benzene , surface modification , molar mass distribution , end group , yield (engineering) , chemistry , lithium (medication) , materials science , organic chemistry , catalysis , polymer , copolymer , metallurgy , medicine , endocrinology
ω‐Formyl‐functionalized polystyrenes can be synthesized in quantitative yield by reacting poly(styryl)lithium ( M n = 2 × 10 3 −8 × 10 3 g/mol) in benzene with a 0.1−0.4 molar excess of 4‐morpholinecarboxaldehyde followed by methanol termination and precipitation into methanol. Narrow molecular weight distribution ω‐formyl‐functionalized polystyrenes were characterized by hydroxylamine end‐group titration, thin layer chromatography and both 1 H and 13 C NMR spectroscopy. The mechanism of the functionalization was studied by trapping the tetrahedral α‐amino alkoxide intermediate with diphenylphosphinic chloride.