Versatile functionalization of aromatic polysulfones via thiol-ene click chemistry

Park, Eun Joo; Lee, Woo-Hyung; Bae, Chulsung

doi:10.1002/pola.28210

Title: Versatile functionalization of aromatic polysulfones via thiol-ene click chemistry

Journal Article · Mon Jun 27 00:00:00 EDT 2016 · Journal of Polymer Science. Part A, Polymer Chemistry

DOI:https://doi.org/10.1002/pola.28210· OSTI ID:1533205

Park, Eun Joo ^[1]; Lee, Woo-Hyung ^[1]; Bae, Chulsung ^[1]

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.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Univ. of Nevada, Reno, NV (United States)

Sponsoring Organization:: USDOE Office of Science (SC); National Science Foundation (NSF); Rensselaer Polytechnic Institute

Grant/Contract Number:: SC0005062; DMR-1506245

OSTI ID:: 1533205

Journal Information:: Journal of Polymer Science. Part A, Polymer Chemistry, Vol. 54, Issue 19; ISSN 0887-624X

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 7 works

Citation information provided by
Web of Science

References (40)

A novel polysulfone-based affinity membrane with high hemocompatibility: preparation and endotoxin elimination performance Huang, Tiefan; Zhang, Mo; Cheng, Lihua RSC Advances, Vol. 3, Issue 48 https://doi.org/10.1039/c3ra43594f	journal	January 2013
Mesoporous Silica Sphere−Polysulfone Mixed Matrix Membranes for Gas Separation Zornoza, Beatriz; Irusta, Silvia; Téllez, Carlos Langmuir, Vol. 25, Issue 10 https://doi.org/10.1021/la900656z	journal	May 2009
Advanced functional polymer membranes Ulbricht, Mathias Polymer, Vol. 47, Issue 7 https://doi.org/10.1016/j.polymer.2006.01.084	journal	March 2006
Thiol-click chemistry: a multifaceted toolbox for small molecule and polymer synthesis Hoyle, Charles E.; Lowe, Andrew B.; Bowman, Christopher N. Chemical Society Reviews, Vol. 39, Issue 4 https://doi.org/10.1039/b901979k	journal	January 2010
Macromolecular Engineering through Click Chemistry and Other Efficient Transformations Sumerlin, Brent S.; Vogt, Andrew P. Macromolecules, Vol. 43, Issue 1 https://doi.org/10.1021/ma901447e	journal	January 2010
Materials for fuel-cell technologies Steele, Brian C. H.; Heinzel, Angelika Nature, Vol. 414, Issue 6861, p. 345-352 https://doi.org/10.1038/35104620	journal	November 2001
Novel network polymer electrolytes based on polysiloxane with internal plasticizer Zhang, Zhengcheng; Fang, Shibi Electrochimica Acta, Vol. 45, Issue 13 https://doi.org/10.1016/S0013-4686(99)00435-1	journal	March 2000
Synthesis of thiol-linked neoglycopolymers and thermo-responsive glycomicelles as potential drug carrier Chen, Gaojian; Amajjahe, Sadik; Stenzel, Martina H. Chemical Communications, Issue 10 https://doi.org/10.1039/b900215d	journal	January 2009
Recent advances in the preparation of functionalized polysulfones: Preparation of functionalized polysulfones Dizman, Cemil; Tasdelen, Mehmet Atilla; Yagci, Yusuf Polymer International, Vol. 62, Issue 7 https://doi.org/10.1002/pi.4525	journal	May 2013
Thiol-Ene Click Chemistry Hoyle, Charles E.; Bowman, Christopher N. Angewandte Chemie International Edition, Vol. 49, Issue 9, p. 1540-1573 https://doi.org/10.1002/anie.200903924	journal	February 2010
Postpolymerization Modification of Poly(dihydropyrimidin-2(1 H )-thione)s via the Thiourea–Haloalkane Reaction to Prepare Functional Polymers Zhao, Yuan; Wu, Haibo; Zhang, Yuanyi ACS Macro Letters, Vol. 4, Issue 8 https://doi.org/10.1021/acsmacrolett.5b00428	journal	July 2015
Chemical modification of polyethersulfone nanofiltration membranes: A review Van der Bruggen, B. Journal of Applied Polymer Science, Vol. 114, Issue 1 https://doi.org/10.1002/app.30578	journal	October 2009
Polymer–trimannoside conjugates via a combination of RAFT and thiol–ene chemistry Roy, Debashish; Ghosn, Bilal; Song, Eun-Ho Polym. Chem., Vol. 4, Issue 4 https://doi.org/10.1039/C2PY20820B	journal	January 2013
PEG-based Multifunctional Polyethers with Highly Reactive Vinyl-Ether Side Chains for Click-Type Functionalization Mangold, Christine; Dingels, Carsten; Obermeier, Boris Macromolecules, Vol. 44, Issue 16 https://doi.org/10.1021/ma200898n	journal	August 2011
Chemical modification of chloromethylated polysulfones via click reactions Gaina, Constantin; Gaina, Viorica; Ionita, Daniela Polymer International, Vol. 60, Issue 2 https://doi.org/10.1002/pi.2948	journal	October 2010
Thiol-ene “click” reactions and recent applications in polymer and materials synthesis Lowe, Andrew B. Polym. Chem., Vol. 1, Issue 1 https://doi.org/10.1039/B9PY00216B	journal	January 2010
Modified polysulfones. IV. Synthesis and characterization of polymers with silicon substituents for a comparative study of gas-transport properties Guiver, Michael D.; Robertson, Gilles P.; Rowe, Sheri Journal of Polymer Science Part A: Polymer Chemistry, Vol. 39, Issue 13 https://doi.org/10.1002/pola.1187	journal	January 2001
Development of Thermal and Photochemical Strategies for Thiol−Ene Click Polymer Functionalization Campos, Luis M.; Killops, Kato L.; Sakai, Ryosuke Macromolecules, Vol. 41, Issue 19 https://doi.org/10.1021/ma801630n	journal	October 2008
Functionalization of Polysulfones by Click Chemistry Toiserkani, Hojjat; Yilmaz, Gorkem; Yagci, Yusuf Macromolecular Chemistry and Physics, Vol. 211, Issue 22 https://doi.org/10.1002/macp.201000245	journal	October 2010
‘Click’ Chemistry in Polymer and Material Science: An Update Binder, Wolfgang H.; Sachsenhofer, Robert Macromolecular Rapid Communications, Vol. 29, Issue 12–13 https://doi.org/10.1002/marc.200800089	journal	July 2008
Facile and versatile platform for the preparation of functional polyethylenes via thiol-ene chemistry Xiao, Zeyun; Bennett, Christopher W.; Connal, Luke A. Journal of Polymer Science Part A: Polymer Chemistry, Vol. 53, Issue 17 https://doi.org/10.1002/pola.27667	journal	April 2015
Strategies for controlling biofouling in membrane filtration systems: challenges and opportunities Mansouri, Jaleh; Harrisson, Simon; Chen, Vicki Journal of Materials Chemistry, Vol. 20, Issue 22 https://doi.org/10.1039/b926440j	journal	January 2010
High-Performance Alkaline Polymer Electrolyte for Fuel Cell Applications Pan, Jing; Lu, Shanfu; Li, Yan Advanced Functional Materials, Vol. 20, Issue 2 https://doi.org/10.1002/adfm.200901314	journal	January 2010
Chemical Modification of Polysulfones: A Facile Method of Preparing Azide Derivatives from Lithiated Polysulfone Intermediates Guiver, Michael D.; Robertson, Gilles P. Macromolecules, Vol. 28, Issue 1 https://doi.org/10.1021/ma00105a041	journal	January 1995
Surface-modified polysulfone hollow fibers. IV. Chloromethylated fibers and their derivatives Higuchi, Akon; Koga, Hiroyuki; Nakagawa, Tsutomu Journal of Applied Polymer Science, Vol. 46, Issue 3 https://doi.org/10.1002/app.1992.070460310	journal	September 1992
Immobilization of alpha lipoic acid onto polysulfone membranes to suppress hemodialysis induced oxidative stress Mahlicli, Filiz Yasar; Altinkaya, Sacide Alsoy Journal of Membrane Science, Vol. 449 https://doi.org/10.1016/j.memsci.2013.07.061	journal	January 2014
Thiol-enes: Chemistry of the past with promise for the future Hoyle, Charles E.; Lee, Tai Yeon; Roper, Todd Journal of Polymer Science Part A: Polymer Chemistry, Vol. 42, Issue 21 https://doi.org/10.1002/pola.20366	journal	January 2004
Backbone stability of quaternized polyaromatics for alkaline membrane fuel cells Fujimoto, Cy; Kim, Dae-Sik; Hibbs, Michael Journal of Membrane Science, Vol. 423-424, p. 438-449 https://doi.org/10.1016/j.memsci.2012.08.045	journal	December 2012
Functional Polymers by Post‐Polymerization Modification: Concepts, Guidelines, and Applications Theato, Patrick; Klok, Harm‐Anton https://doi.org/10.1002/9783527655427	book	October 2012
Dynamic mechanical behavior of polysulfones Aitken, C. L.; McHattie, J. S.; Paul, D. R. Macromolecules, Vol. 25, Issue 11 https://doi.org/10.1021/ma00037a020	journal	May 1992
Separation characteristics of modified polysulfone ultrafiltration membranes using NOx Chowdhury, S. Roy; Kumar, P.; Bhattacharya, P. K. Separation and Purification Technology, Vol. 24, Issue 1-2 https://doi.org/10.1016/S1383-5866(01)00130-7	journal	June 2001
Highly Efficient Incorporation of Functional Groups into Aromatic Main-Chain Polymer Using Iridium-Catalyzed C−H Activation and Suzuki−Miyaura Reaction Jo, Tae Soo; Kim, Se Hye; Shin, Jihoon Journal of the American Chemical Society, Vol. 131, Issue 5 https://doi.org/10.1021/ja808374e	journal	February 2009
The Thiol-Michael Addition Click Reaction: A Powerful and Widely Used Tool in Materials Chemistry Nair, Devatha P.; Podgórski, Maciej; Chatani, Shunsuke Chemistry of Materials, Vol. 26, Issue 1 https://doi.org/10.1021/cm402180t	journal	September 2013
Modification methods for poly(arylsulfone) membranes: A mini-review focusing on surface modification Nady, Norhan; Franssen, Maurice C. R.; Zuilhof, Han Desalination, Vol. 275, Issue 1-3 https://doi.org/10.1016/j.desal.2011.03.010	journal	July 2011
Triple Click Reaction Strategy for Macromolecular Diversity Tunca, Umit Macromolecular Rapid Communications, Vol. 34, Issue 1 https://doi.org/10.1002/marc.201200656	journal	November 2012
Water purification by membranes: The role of polymer science Geise, Geoffrey M.; Lee, Hae-Seung; Miller, Daniel J. Journal of Polymer Science Part B: Polymer Physics, Vol. 48, Issue 15 https://doi.org/10.1002/polb.22037	journal	June 2010
Experimental investigation of the permeability and selectivity of supported ionic liquid membranes for CO₂/He separation at temperatures up to 125°C Ilconich, Jeffery; Myers, Christina; Pennline, Henry Journal of Membrane Science, Vol. 298, Issue 1-2, p. 41-47 https://doi.org/10.1016/j.memsci.2007.03.056	journal	July 2007
Chemically modified polysulfone hollow fibers with vinylpyrrolidone having improved blood compatibility Higuchi, Akon; Shirano, Kazunobu; Harashima, Masaharu Biomaterials, Vol. 23, Issue 13 https://doi.org/10.1016/S0142-9612(01)00406-9	journal	July 2002
Functional group polysulphones by bromination-metalation Guiver, Michael D.; Kutowy, O.; ApSimon, John W. Polymer, Vol. 30, Issue 6 https://doi.org/10.1016/0032-3861(89)90094-3	journal	June 1989
An improved method for surface modification of porous water purification membranes Miller, Daniel J.; Paul, Donald R.; Freeman, Benny D. Polymer, Vol. 55, Issue 6 https://doi.org/10.1016/j.polymer.2014.01.046	journal	March 2014

Cited By (3)

C‐H‐Funktionalisierung von Standardpolymeren Williamson, Jill B.; Lewis, Sally E.; Johnson, Robert R. Angewandte Chemie, Vol. 131, Issue 26 https://doi.org/10.1002/ange.201810970	journal	March 2019
C−H Functionalization of Commodity Polymers Williamson, Jill B.; Lewis, Sally E.; Johnson, Robert R. Angewandte Chemie International Edition, Vol. 58, Issue 26 https://doi.org/10.1002/anie.201810970	journal	June 2019
The emerging applications of click chemistry reactions in the modification of industrial polymers Arslan, Mehmet; Acik, Gokhan; Tasdelen, Mehmet Atilla Polymer Chemistry, Vol. 10, Issue 28 https://doi.org/10.1039/c9py00510b	journal	January 2019

Similar Records

Thiol–ene Click Chemistry Incorporates Hydroxyl Functionality on Polycyclooctene to Tune Properties

Journal Article · Thu Jan 05 00:00:00 EST 2023 · ACS Macro Letters · OSTI ID:1533205

Chethalen, Roshni John; Fastow, Eli J.; Coughlin, E. Bryan; +1 more

Liquid crystalline networks based on photo-initiated thiol–ene click chemistry

Journal Article · Tue Dec 10 00:00:00 EST 2019 · Soft Matter (Online) · OSTI ID:1533205

Li, Yuzhan; Zhang, Yuehong; Goswami, Monojoy; +10 more

Versatility of Alkyne-Modified Poly(Glycidyl Methacrylate) Layers for Click Reactions

Journal Article · Sat Jan 01 00:00:00 EST 2011 · Langmuir · OSTI ID:1533205

Soto-Cantu, Dr. Erick; Lokitz, Bradley S; Hinestrosa Salazar, Juan Pablo; +3 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
polymer science
click chemistry
functionalization of polymers
modification
polysulfone
poly(ether sulfones)
postpolymerization modification
thiol-ene chemistry

Title: Versatile functionalization of aromatic polysulfones via thiol-ene click chemistry

Citation Formats

References (40)

Cited By (3)

Similar Records

Related Subjects