Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

Versatile functionalization of aromatic polysulfones via thiol-ene click chemistry

Journal Article · · Journal of Polymer Science. Part A, Polymer Chemistry
DOI:https://doi.org/10.1002/pola.28210· OSTI ID:1533205
 [1];  [2];  [2]
  1. Rensselaer Polytechnic Inst., Troy, NY (United States); DOE/OSTI
  2. Rensselaer Polytechnic Inst., Troy, NY (United States)
A facile, efficient approach for preparation of functionalized aromatic polysulfones by postpolymerization modification with thiol-ene click chemistry is described. The key synthetic strategy is to incorporate a pendant vinyl ether group into polysulfones as a reactive precursor with controlled degrees of functionalization. Synthetic utility of the pendant alkenyl group is demonstrated by generating diverse polymer derivatives using thiol-ene functionalization including glycosylated polysulfone. Finally, the highly reactive alkene platform in the polymer affords convenient, metal-free, and azide-free click transformations to create diverse ranges of new functionalized polysulfones that could be applied in various applications.
Research Organization:
Univ. of Nevada, Reno, NV (United States)
Sponsoring Organization:
National Science Foundation (NSF); Rensselaer Polytechnic Institute; USDOE Office of Science (SC)
Grant/Contract Number:
SC0005062
OSTI ID:
1533205
Journal Information:
Journal of Polymer Science. Part A, Polymer Chemistry, Journal Name: Journal of Polymer Science. Part A, Polymer Chemistry Journal Issue: 19 Vol. 54; ISSN 0887-624X
Publisher:
WileyCopyright Statement
Country of Publication:
United States
Language:
English

References (40)

Functional Polymers by Post‐Polymerization Modification: Concepts, Guidelines, and Applications book October 2012
High-Performance Alkaline Polymer Electrolyte for Fuel Cell Applications journal January 2010
Thiol-Ene Click Chemistry journal February 2010
Surface-modified polysulfone hollow fibers. IV. Chloromethylated fibers and their derivatives journal September 1992
Chemical modification of polyethersulfone nanofiltration membranes: A review journal October 2009
Functionalization of Polysulfones by Click Chemistry journal October 2010
‘Click’ Chemistry in Polymer and Material Science: An Update journal July 2008
Triple Click Reaction Strategy for Macromolecular Diversity journal November 2012
Chemical modification of chloromethylated polysulfones via click reactions journal October 2010
Recent advances in the preparation of functionalized polysulfones: Preparation of functionalized polysulfones journal May 2013
Modified polysulfones. IV. Synthesis and characterization of polymers with silicon substituents for a comparative study of gas-transport properties journal January 2001
Thiol-enes: Chemistry of the past with promise for the future journal January 2004
Facile and versatile platform for the preparation of functional polyethylenes via thiol-ene chemistry journal April 2015
Water purification by membranes: The role of polymer science journal June 2010
Functional group polysulphones by bromination-metalation journal June 1989
Novel network polymer electrolytes based on polysiloxane with internal plasticizer journal March 2000
Chemically modified polysulfone hollow fibers with vinylpyrrolidone having improved blood compatibility journal July 2002
Separation characteristics of modified polysulfone ultrafiltration membranes using NOx journal June 2001
Modification methods for poly(arylsulfone) membranes: A mini-review focusing on surface modification journal July 2011
Experimental investigation of the permeability and selectivity of supported ionic liquid membranes for CO2/He separation at temperatures up to 125°C journal July 2007
Backbone stability of quaternized polyaromatics for alkaline membrane fuel cells journal December 2012
Immobilization of alpha lipoic acid onto polysulfone membranes to suppress hemodialysis induced oxidative stress journal January 2014
Advanced functional polymer membranes journal March 2006
An improved method for surface modification of porous water purification membranes journal March 2014
Postpolymerization Modification of Poly(dihydropyrimidin-2(1 H )-thione)s via the Thiourea–Haloalkane Reaction to Prepare Functional Polymers journal July 2015
The Thiol-Michael Addition Click Reaction: A Powerful and Widely Used Tool in Materials Chemistry journal September 2013
Highly Efficient Incorporation of Functional Groups into Aromatic Main-Chain Polymer Using Iridium-Catalyzed C−H Activation and Suzuki−Miyaura Reaction journal February 2009
Mesoporous Silica Sphere−Polysulfone Mixed Matrix Membranes for Gas Separation journal May 2009
Dynamic mechanical behavior of polysulfones journal May 1992
Chemical Modification of Polysulfones: A Facile Method of Preparing Azide Derivatives from Lithiated Polysulfone Intermediates journal January 1995
PEG-based Multifunctional Polyethers with Highly Reactive Vinyl-Ether Side Chains for Click-Type Functionalization journal August 2011
Development of Thermal and Photochemical Strategies for Thiol−Ene Click Polymer Functionalization journal October 2008
Macromolecular Engineering through Click Chemistry and Other Efficient Transformations journal January 2010
Materials for fuel-cell technologies journal November 2001
Thiol-ene “click” reactions and recent applications in polymer and materials synthesis journal January 2010
Polymer–trimannoside conjugates via a combination of RAFT and thiol–ene chemistry journal January 2013
Synthesis of thiol-linked neoglycopolymers and thermo-responsive glycomicelles as potential drug carrier journal January 2009
Thiol-click chemistry: a multifaceted toolbox for small molecule and polymer synthesis journal January 2010
Strategies for controlling biofouling in membrane filtration systems: challenges and opportunities journal January 2010
A novel polysulfone-based affinity membrane with high hemocompatibility: preparation and endotoxin elimination performance journal January 2013

Cited By (3)

C‐H‐Funktionalisierung von Standardpolymeren journal March 2019
C−H Functionalization of Commodity Polymers journal June 2019
The emerging applications of click chemistry reactions in the modification of industrial polymers journal January 2019