Premium
Soluble Polystyrenes Functionalized by Triorgano[(1‐oxoalkyl)oxy]stannanes (=Triorganotin Carboxylates): Synthesis, Structure, and Anion‐Recognition Characteristics
Author(s) -
Dalil Hassan,
Biesemans Monique,
Willem Rudolph,
Angiolini Luigi,
Salatelli Elisabetta,
Caretti Daniele,
Chaniotakis Nikolas A.,
Perdikaki Katerina
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200203)85:3<852::aid-hlca852>3.0.co;2-m
Subject(s) - chemistry , styrene , copolymer , polystyrene , polymer chemistry , hydrolysis , stannane , polymer , medicinal chemistry , organic chemistry
Polystyrene copolymers of the type ( P −H) 1− x ( P −(CH 2 ) n −COOSnR 3 ) x containing [(1‐oxoalkyl)oxy]triphenylstannane or tributyl[(1‐oxoalkyl)oxy]stannanes as side chains ( P −H=styrene; P −(CH 2 ) n −COOSnR 3 = para ‐substituted styrene‐like monomeric unit with R=Ph ( x =0.1), Bu ( x =0.5); n =2–4) were investigated. The tributyl[(1‐oxoalkyl)oxy]stannane copolymer was prepared by direct conversion of the corresponding copolymeric methyl esters with hexabutyldistannoxane. By contrast, the [(1‐oxoalkyl)oxy]triphenylstannane copolymer could be prepared only by a procedure involving two reaction steps consisting of a preliminary hydrolysis of the related methyl ester ( P −H) 1‐ x ( P −(CH 2 ) n −COOMe) x followed by functionalization of the corresponding poly(carboxylic acid) ( P −H) 1‐ x ( P −(CH 2 n −COOH) x with hydroxytriphenylstannane. Attempts to directly convert the methyl ester with hydroxytriphenylstannane or hexaphenyldistannoxane led to the formation of uncompletely functionalized product. The structure of the stannane‐functionalized polymers was investigated in solution and solid state by NMR, IR, and thermal analysis. The tributylstannane and triphenylstannane copolymers were assessed as chloride‐selective anion carriers in polymeric‐liquid‐membrane potentiometric ion‐selective electrodes.