Modified polysulfones. VI. Preparation of polymer membrane materials containing benzimine and benzylamine groups as precursors for molecularly imprinted sensor devices

Abstract

A modified polysulfone containing benzylamine groups was synthesized as a reactive membrane material. Polysulfone was activated at the ortho-sulfone site by direct lithiation with n-butyllithium, and the resulting lithiated polysulfone was then reacted with benzonitrile; this yielded a polymer with pendant benzimine groups. The structure was confirmed by NMR and IR spectroscopy and by the transformation of imine to ketone by acid hydrolysis. The polymeric benzimine was also reduced to benzylamine with sodium cyanoborohydride in an acidic medium. The structure and degree of substitution of both benzylamine derivatives were determined by NMR and IR spectroscopy. The modified polysulfone containing benzylamine groups initiated the polymerization of N-carboxyanhydride of ␥-benzyl-L-glutamate [Glu(OBzl)-NCA]. The side-chain oligopeptide of Glu(OBzl)-NCA attached to polysulfone was converted into molecular recognition sites.

Polypeptide und 100 Jahre Chemie der α‐Aminosäure‐N‐carboxyanhydride

“…[208] Poly(g-Bzl-l-Glu) wurde auch auf Polyethersulfonen der Struktur 77 aufgepfropft, mit dem Ziel, molekular geprägte Sensoreinheiten zu erzeugen. [209] Ferner wurde g-Bzl-l-Glu-NCA auf poröse Omnipore-Membranen polymerisiert. Diese Membranen bestanden aus einem Ethylen-Tetrafluorethylen-Copolymerisat, das durch einen elektrochemischen Prozess mit Aminogruppen modifiziert war.…”

Evaluation of the recognition ability of molecularly imprinted materials by surface plasmon resonance (SPR) spectroscopy

“…PSf, having a degree of substitution (DS) of 0.9, was prepared by the modification of polysulfone Udel P-3500 as reported previously [30]. Following similar procedures for the present study, commercial polysulfone was lithiated with 1.0 mol equivalents of n-butyllithium, quenched with benzonitrile, then reduced with sodium borohydride to give PSf with DS 0.9.…”

Phenyltrimethylammonium Functionalized Polysulfone Anion Exchange Membranes

“…47,48 The copolymers 2 were converted to quaternized polysulfones by reaction with iodomethane. The mole ratio of iodomethane to phenyldimethyl amine groups was 2:1 to ensure complete quaternization of the tertiary amine units into the bis(phenyltrimethylammonium) (PTMA) substituents and −OH into −OCH 3 groups.…”