title: Click Functionalization of a Dibenzocyclooctyne-Containing Conjugated Polyimine.
abstract: A conjugated poly(phenyl-co-dibenzocyclooctyne) Schiff-base polymer, prepared through polycondensation of dibenzocyclooctyne bisamine (DIBO-(NH2)2) with bis(hexadecyloxy)phenyldialdehyde, is reported. The resulting polymer, which has a high molecular weight (M(n)>30 kDa, M(w)>60 kDa), undergoes efficient strain-promoted alkyne-azide cycloaddition reactions with a series of azides. This enables quantitative modification of each repeat unit within the polymer backbone and the rapid synthesis of a conjugated polymer library with widely different substituents but a consistent degree of polymerization (DP). Kinetic studies show a second-order reaction rate constant that is consistent with monomeric dibenzocyclooctynes. Grafting with azide-terminated polystyrene and polyethylene glycol monomethyl ether chains of varying molecular weight resulted in the efficient syntheses of a series of graft copolymers with a conjugated backbone and maximal graft density.
authors.affiliation: Department of Chemistry, McMaster University, 1280 Main St. W., Hamilton, ON, L8S 4M1, Canada.
authors.forename: Vladimir
authors.initials: V
authors.lastname: Kardelis
authors.affiliation: Department of Chemistry, McMaster University, 1280 Main St. W., Hamilton, ON, L8S 4M1, Canada.
authors.forename: Ryan C
authors.initials: RC
authors.lastname: Chadwick
authors.affiliation: Department of Chemistry, McMaster University, 1280 Main St. W., Hamilton, ON, L8S 4M1, Canada. adronov@mcmaster.ca.
authors.forename: Alex
authors.identifier: http://orcid.org/0000-0002-0770-3118
authors.initials: A
authors.lastname: Adronov
keywords: click chemistry; conjugated polymers; graft copolymers; polymer modification; polymers