Prepolymerization and postpolymerization functionalization approaches to fluorescent conjugated carbazole‐based glycopolymers via “click chemistry”

Abstract

Facile prepolymerization and postpolymerization functionalization approaches to prepare well‐defined fluorescent conjugated glycopolymers through Cu(I)‐catalyzed azide/alkyne “Click” ligation were explored. Two well‐defined carbazole‐based fluorescent conjugated glycopolymers were readily synthesized based on these strategies and characterized by 1H NMR, 13C NMR, IR spectra, and UV‐vis spectra. The “Click” ligation offers a very effective conjugation method to covalently attach carbohydrate residues to fluorescent conjugated polymers. In addition, the studies of carbohydrate–lectin interactions were performed by titration of concanavalin A (Con A) to D‐glucose‐bearing poly(anthracene‐alt‐carbazole) copolymer P‐2 resulting in significant fluorescence quenching of the polymer due to carbohydrate–lectin interactions. When peanut agglutinin (PNA) was added, no distinct change in the fluorescent properties of P‐2 was observed. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 2948–2957, 2009

The power of thiol‐ene chemistry

“…Both photochemical and thermal radical conditions were tested to explore the efficiency of the thiol‐ene reaction, and it was found that using photochemical conditions leads to faster and, in many cases, quantitative reaction. The authors also verified the orthogonality of thiol‐ene with copper catalyzed azide‐alkyne cycloaddition (CuAAC) 43–45. Ma et al studied a series of monomers containing alkenes and their usage for the synthesis of homopolymers, block copolymers, and random copolymers 46.…”

Triphenylamine‐based fluorescent conjugated copolymers with pendant terpyridyl ligands as chemosensors for metal ions

“…We have reported the synthesis of various FCPs with pendant carbohydrates and their interactions with lectins or DNA 27–29. To extend the potential application of FCPs in chemo‐ and biosensing, herein, two well‐defined triphenylamine‐based conjugated polymers containing terpyridyl ligands were synthesized (Scheme ) and well characterized using 1 H‐NMR, 13 C‐NMR, Infrared (IR), and UV‐vis spectra.…”

Glucosamine Hydrochloride Functionalized Water‐Soluble Conjugated Polyfluorene: Synthesis, Characterization, and Interactions with DNA

“…[14] Using those methods, triphenylamine-based conjugated glycopolymers were prepared for studies of specific carbohydrate-lectin interaction. [15] However, positively charged fluorescent conjugated glycopolymers for detecting polyanions based on electrostatic interaction have not been reported.…”

“…With high efficiencies in both photoluminescence and electroluminescence, polyfluorene derivatives have gained much attention during the past decade as versatile active materials in optoelectronic devices and fluorescent sensory materials. [16] In this communication, cationic water-soluble conjugated polyfluorene with pendant glucosamine hydrochloride (P-2) was easily synthesized through the prepolymerization functionalization approach, [14] which is based on Cu(I)-catalyzed azide/ alkyne ''click'' ligation [17] and Suzuki coupling polymerization. The preliminary study of P-2-single-stranded DNA (ssDNA) interaction was performed by a series of spectrofluorometric titration.…”