Date/Time
Date(s) - 19/08/2021
1:30 pm - 2:30 pm

Title: Post-Polymerization Click Functionalization of Conjugated Polymers 

Date: Thursday, August 19, 2021 

Time: 1:30-2:30 

Zoom (link available by contacting macchem@mcmaster.ca)

Host: Dr. Alex Adronov 

Abstract: Conjugated polymers attract significant attention due to their interesting optoelectronic and physical properties.¹ Moreover, functionalization of conjugated polymers is crucial for tailoring their performance in any given application.² To create a tunable conjugated polymer, a poly(phenyl-co-dibenzocyclooctyne) polyimine was synthesized via condensation of dibenzocyclooctyne bisamine (DIBO-(NH₂)₂) and bis(hexadecyloxy)dialdehyde. Strain-promoted alkyne-azide cycloaddition (SPAAC) with a series of aryl azides allowed efficient functionalization of triazole moieties on the resultant polymer’s backbone and the rapid synthesis of a small polymer library with a consistent degree of polymerization (DP). Grafting with polystyrene and polyethylene glycol azide-terminated polymers allowed the efficient syntheses of a series of graft-co-polymers with M_n values up to 800 kDa and varying solubilities. To improve on the stability and robustness of tunable conjugated polymers, a poly(tetrazine-co-fluorene) conjugated polymer was synthesized via Suzuki polycondensation of bisfuran-s-tetrazine dibromide with fluorene-diboronic acid bis(pinacol) ester. An inverse-electron-demand Diels-Alder reaction of the s-tetrazine repeat units with trans-cyclooctene derivatives resulted in the rapid and quantitative functionalization of the conjugated polymer backbone. These reactive conjugated polymers were explored in a variety of applications, including supramolecular chemistry and gel formation. 

[1] Facchetti, A. Chem. Mater. 2011, 23, 733 – 758.

[2] Swager, T. M. Macromolecules. 2017, 50, 4867-4886.