Novel cross-linked polystyrenes with large space network as tailor-made catalyst supports for sustainable media
Abstract
For a novel class of polystyrene-based gel-type resins (SPACeR, SP), containing the large 1,4-bis (4-vinylphenoxy)benzene cross-linker, is introduced; SP-immobilized 1,5,7-triazabicyclo [4.4.0]dec-5-ene (TBD) and triethylamine (TEA) bases are synthesized and characterized in terms of their structural, thermal and morphological features, and their catalytic efficiency in a series of fundamental chemical transformations under solvent-free conditions is investigated.
- Authors:
-
- Univ. of Perugia (Italy)
- Hasselt Univ., Diepenbeek (Belgium)
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
- Publication Date:
- Research Org.:
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Sciences (CNMS)
- Sponsoring Org.:
- USDOE Office of Science (SC)
- OSTI Identifier:
- 1265889
- Grant/Contract Number:
- AC05-00OR22725
- Resource Type:
- Accepted Manuscript
- Journal Name:
- European Polymer Journal
- Additional Journal Information:
- Journal Volume: 73; Journal Issue: C; Journal ID: ISSN 0014-3057
- Publisher:
- Elsevier
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 36 MATERIALS SCIENCE
Citation Formats
Marrocchi, Assunta, Adriaensens, Peter, Bartollini, Elena, Barkakaty, Balaka, Carleer, Robert, Chen, Jihua, Hensley, Dale K., Petrucci, Chiara, Tassi, Marco, and Vaccaro, Luigi. Novel cross-linked polystyrenes with large space network as tailor-made catalyst supports for sustainable media. United States: N. p., 2015.
Web. doi:10.1016/j.eurpolymj.2015.10.002.
Marrocchi, Assunta, Adriaensens, Peter, Bartollini, Elena, Barkakaty, Balaka, Carleer, Robert, Chen, Jihua, Hensley, Dale K., Petrucci, Chiara, Tassi, Marco, & Vaccaro, Luigi. Novel cross-linked polystyrenes with large space network as tailor-made catalyst supports for sustainable media. United States. https://doi.org/10.1016/j.eurpolymj.2015.10.002
Marrocchi, Assunta, Adriaensens, Peter, Bartollini, Elena, Barkakaty, Balaka, Carleer, Robert, Chen, Jihua, Hensley, Dale K., Petrucci, Chiara, Tassi, Marco, and Vaccaro, Luigi. Fri .
"Novel cross-linked polystyrenes with large space network as tailor-made catalyst supports for sustainable media". United States. https://doi.org/10.1016/j.eurpolymj.2015.10.002. https://www.osti.gov/servlets/purl/1265889.
@article{osti_1265889,
title = {Novel cross-linked polystyrenes with large space network as tailor-made catalyst supports for sustainable media},
author = {Marrocchi, Assunta and Adriaensens, Peter and Bartollini, Elena and Barkakaty, Balaka and Carleer, Robert and Chen, Jihua and Hensley, Dale K. and Petrucci, Chiara and Tassi, Marco and Vaccaro, Luigi},
abstractNote = {For a novel class of polystyrene-based gel-type resins (SPACeR, SP), containing the large 1,4-bis (4-vinylphenoxy)benzene cross-linker, is introduced; SP-immobilized 1,5,7-triazabicyclo [4.4.0]dec-5-ene (TBD) and triethylamine (TEA) bases are synthesized and characterized in terms of their structural, thermal and morphological features, and their catalytic efficiency in a series of fundamental chemical transformations under solvent-free conditions is investigated.},
doi = {10.1016/j.eurpolymj.2015.10.002},
journal = {European Polymer Journal},
number = C,
volume = 73,
place = {United States},
year = {Fri Oct 09 00:00:00 EDT 2015},
month = {Fri Oct 09 00:00:00 EDT 2015}
}
Free Publicly Available Full Text
Publisher's Version of Record
Other availability
Search WorldCat to find libraries that may hold this journal
Cited by: 26 works
Citation information provided by
Web of Science
Web of Science
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
Catalyst Enhancement and Recyclability by Immobilization of Metal Complexes onto Graphene Surface by Noncovalent Interactions
journal, April 2014
- Sabater, Sara; Mata, Jose A.; Peris, Eduardo
- ACS Catalysis, Vol. 4, Issue 6
Stereoselective organic reactions promoted by immobilized chiral catalysts in continuous flow systems
journal, January 2013
- Puglisi, Alessandra; Benaglia, Maurizio; Chiroli, Valerio
- Green Chemistry, Vol. 15, Issue 7
Highly cross-linked imidazolium salt entrapped magnetic particles – preparation and applications
journal, January 2012
- Agrigento, Paola; Beier, Matthias J.; Knijnenburg, Jesper T. N.
- Journal of Materials Chemistry, Vol. 22, Issue 38
Polymer-supported Pd–NHC complexes: Strategies for the development of multifunctional systems
journal, November 2012
- Sans, V.; Gelat, F.; Burguete, M. I.
- Catalysis Today, Vol. 196, Issue 1
Porous polymer particles—A comprehensive guide to synthesis, characterization, functionalization and applications
journal, March 2012
- Gokmen, M. Talha; Du Prez, Filip E.
- Progress in Polymer Science, Vol. 37, Issue 3
Polymer Cocktail: A Multitask Supported Ionic Liquid-Like Species to Facilitate Multiple and Consecutive CC Coupling Reactions
journal, November 2010
- Sans, Victor; Gelat, Fabien; Karbass, Naima
- Advanced Synthesis & Catalysis, Vol. 352, Issue 17
Polymer‐Supported Chiral Organocatalysts: Synthetic Strategies for the Road Towards Affordable Polymeric Immobilization
journal, May 2010
- Kristensen, Tor E.; Hansen, Tore
- European Journal of Organic Chemistry, Vol. 2010, Issue 17
Solid Phase Peptide Synthesis. I. The Synthesis of a Tetrapeptide
journal, July 1963
- Merrifield, R. B.
- Journal of the American Chemical Society, Vol. 85, Issue 14, p. 2149-2154
Organic Polymer Supports for Synthesis and for Reagent and Catalyst Immobilization
journal, January 2009
- Lu, Jinni; Toy, Patrick H.
- Chemical Reviews, Vol. 109, Issue 2
Aspects of Immobilisation of Catalysts on Polymeric Supports
journal, August 2006
- Dioos, Bart M. L.; Vankelecom, Ivo F. J.; Jacobs, Pierre A.
- Advanced Synthesis & Catalysis, Vol. 348, Issue 12-13
Immobilization of Organic Catalysts: When, Why, and How
journal, August 2006
- Cozzi, Franco
- Advanced Synthesis & Catalysis, Vol. 348, Issue 12-13
Polymer-Supported Organic Catalysts †
journal, September 2003
- Benaglia, Maurizio; Puglisi, Alessandra; Cozzi, Franco
- Chemical Reviews, Vol. 103, Issue 9
Recoverable Catalysts and Reagents Using Recyclable Polystyrene-Based Supports
journal, October 2002
- McNamara, Catherine A.; Dixon, Mark J.; Bradley, Mark
- Chemical Reviews, Vol. 102, Issue 10
Preparation, structure and morphology of polymer supports
journal, January 1998
- Sherrington, David C.
- Chemical Communications, Issue 21
Asymmetric Diels−Alder Reaction of Methacrolein with Cyclopentadiene Using Polymer-Supported Catalysts: Design of Highly Enantioselective Polymeric Catalysts
journal, January 1996
- Kamahori, Koichi; Ito, Koichi; Itsuno, Shinichi
- The Journal of Organic Chemistry, Vol. 61, Issue 23
On the planarity of amide nitrogen. Intrinsic pyramidal nitrogen of N-acyl-7-azabicyclo[2.2.1]heptanes
journal, February 1998
- Ohwada, Tomohiko; Achiwa, Takuji; Okamoto, Iwao
- Tetrahedron Letters, Vol. 39, Issue 8
POEPOP and POEPS: Inert polyethylene glycol crosslinked polymeric supports for solid synthesis
journal, August 1996
- Renil, Manat; Meldal, Morten
- Tetrahedron Letters, Vol. 37, Issue 34
Solvent and Reagent Accessibility within Oligo(ethylene glycol) Ether [PEG] Cross-Linked Polystyrene Beads
journal, July 1998
- Wilson, Mark E.; Paech, Kolja; Zhou, Wen-Jing
- The Journal of Organic Chemistry, Vol. 63, Issue 15
Synthesis of peptide-N-alkylamides on a new PS-TTEGDA polymer support using photolabile anchoring group
journal, August 1999
- Kumar, K. S.; Rajasekharan Pillai, V. N.
- Tetrahedron, Vol. 55, Issue 34
Polymer-supported tertiaryphosphine (JJ–TPP) as a green and recyclable organocatalyst for α-addition of carbon nucleophiles to α,β-unsaturated compounds
journal, February 2008
- Liu, Hai-Ling; Jiang, Huan-Feng
- Tetrahedron, Vol. 64, Issue 9
Solvent-free heterogeneous organocatalysis: stereoselective isomerization of α,β-ynones to (E,E)-α,β-γ,δ-dienones catalyzed by polymer-supported tertiaryphosphines
journal, November 2007
- Liu, Hai-Ling; Jiang, Huan-Feng; Xu, Lin
- Tetrahedron Letters, Vol. 48, Issue 47
A multipolymer system for organocatalytic alcohol oxidation
journal, January 2005
- But, Tracy Yuen Sze; Tashino, Yousuke; Togo, Hideo
- Organic & Biomolecular Chemistry, Vol. 3, Issue 6
Optimization of polystyrene-supported triphenylphosphine catalysts for aza-Morita–Baylis–Hillman reactions
journal, December 2005
- Zhao, Lin-Jing; Kwong, Cathy Kar-Wing; Shi, Min
- Tetrahedron, Vol. 61, Issue 51
Smart cleavage reactions: the synthesis of benzimidazoles and benzothiazoles from polymer-bound esters
journal, January 2004
- Matsushita, Hana; Lee, Sang-Hyeup; Joung, Meyoungju
- Tetrahedron Letters, Vol. 45, Issue 2
Smart Cleavage Reactions: the Synthesis of an Array of Ureas from Polymer-Bound Carbamates
journal, September 2004
- Lee, Sang-Hyeup; Matsushita, Hana; Koch, Guido
- Journal of Combinatorial Chemistry, Vol. 6, Issue 5
Polystyrene-Supported Phosphine-Catalyzed aza-Baylis−Hillman Reactions and the Relationship between Resin Loading Level and Catalyst Efficiency
journal, September 2004
- Zhao, Lin-Jing; He, Helen Song; Shi, Min
- Journal of Combinatorial Chemistry, Vol. 6, Issue 5
Synthesis and characterization of novel polystyrene-supported TBD catalysts and their use in the Michael addition for the synthesis of Warfarin and its analogues
journal, January 2014
- Alonzi, Matteo; Bracciale, Maria Paola; Broggi, Alessandra
- Journal of Catalysis, Vol. 309
Palladium Supported on Cross-Linked Imidazolium Network on Silica as Highly Sustainable Catalysts for the Suzuki Reaction under Flow Conditions
journal, June 2013
- Pavia, Cinzia; Ballerini, Eleonora; Bivona, Lucia Anna
- Advanced Synthesis & Catalysis, Vol. 355, Issue 10
Rasta resin as support for TBD in base-catalyzed organic processes
journal, January 2012
- Bonollo, Simona; Lanari, Daniela; Angelini, Tommaso
- Journal of Catalysis, Vol. 285, Issue 1
E-factor minimized protocols for the polystyryl-BEMP catalyzed conjugate additions of various nucleophiles to α,β-unsaturated carbonyl compounds
journal, January 2012
- Bonollo, Simona; Lanari, Daniela; Longo, Julie M.
- Green Chem., Vol. 14, Issue 1
Preparation and Use of Polystyryl-DABCOF2: An Efficient Recoverable and Reusable Catalyst for β-Azidation of α,β-Unsaturated Ketones in Water
journal, February 2012
- Angelini, Tommaso; Lanari, Daniela; Maggi, Raimondo
- Advanced Synthesis & Catalysis, Vol. 354, Issue 5
Solvent-Free Organic Synthesis
journal, March 2000
- Tanaka, K.; Toda, F.
- Chemical Reviews, Vol. 100, Issue 3
A General and Efficient Method for the Selective Synthesis of β-Hydroxy Sulfides and β-Hydroxy Sulfoxides Catalyzed by Gallium(III) Triflate
journal, May 2007
- Su, Weike; Chen, Jiuxi; Wu, Huayue
- The Journal of Organic Chemistry, Vol. 72, Issue 12
Polystyryl-supported TBD as an efficient and reusable catalyst under solvent-free conditions
journal, January 2004
- Fringuelli, Francesco; Pizzo, Ferdinando; Vittoriani, Carla
- Chemical Communications, Issue 23
Cooperative Catalysis for the First Asymmetric Formal [3+2] Cycloaddition Reaction of Isocyanoacetates to α,β-Unsaturated Ketones
journal, May 2011
- Arróniz, Carlos; Gil-González, Alberto; Semak, Vladislav
- European Journal of Organic Chemistry, Vol. 2011, Issue 20-21
A Convenient Method for the Preparation of 4-Aryloxyphenols
journal, January 1991
- Yeager, Gary W.; Schissel, David N.
- Synthesis, Vol. 1991, Issue 01
Works referencing / citing this record:
Chiral catalysts immobilized on achiral polymers: effect of the polymer support on the performance of the catalyst
journal, January 2018
- Altava, Belén; Burguete, M. Isabel; García-Verdugo, Eduardo
- Chemical Society Reviews, Vol. 47, Issue 8
A tailored polymeric cationic tag–anionic Pd( ii ) complex as a catalyst for the low-leaching Heck–Mizoroki coupling in flow and in biomass-derived GVL
journal, January 2019
- Mahmoudi, Hamed; Valentini, Federica; Ferlin, Francesco
- Green Chemistry, Vol. 21, Issue 2
A continuous flow approach for the C–H functionalization of 1,2,3-triazoles in γ-valerolactone as a biomass-derived medium
journal, January 2018
- Ferlin, Francesco; Luciani, Lorenzo; Santoro, Stefano
- Green Chemistry, Vol. 20, Issue 12
Boosting biomass valorisation. Synergistic design of continuous flow reactors and water-tolerant polystyrene acid catalysts for a non-stop production of esters
journal, January 2018
- Trombettoni, Valeria; Sciosci, Daniele; Bracciale, Maria Paola
- Green Chemistry, Vol. 20, Issue 14
Synthesis of β-Cyano Ketones Promoted by a Heterogeneous Fluoride Catalyst
journal, June 2016
- Strappaveccia, Giacomo; Angelini, Tommaso; Bianchi, Luca
- Advanced Synthesis & Catalysis, Vol. 358, Issue 13
Synthesis, characterization and catalytic activity of novel large network polystyrene-immobilized organic bases
journal, January 2015
- Tassi, Marco; Bartollini, Elena; Adriaensens, Peter
- RSC Advances, Vol. 5, Issue 130
Poly(vinylbenzyl chloride- co -divinyl benzene) polyHIPE monolith-supported o -hydroxynaphthaldehyde propylenediamine Schiff base ligand complex of copper( ii ) ions as a catalyst for the epoxidation of cyclohexene
journal, January 2019
- Moghe, Keerti; Sutar, A. K.; Kang, I. K.
- RSC Advances, Vol. 9, Issue 53