Azolium hydrogen carbonates and azolium carboxylates as organic pre-catalysts for N-heterocyclic carbene-catalysed group transfer and ring-opening polymerisations

Literature Information

Publication Date 2013-01-25
DOI 10.1039/C2PY20915B
Impact Factor 5.582
Authors


View Original

Abstract

Various imidazolium-2-carboxylates and (benz)imidazolium hydrogen carbonates, denoted as NHC–CO2 adducts and [NHC(H)][HCO3], respectively, were employed as masked N-heterocyclic carbenes (NHCs) to bring about both the ring opening polymerisation (ROP) of D,L-lactide (LA) and the group transfer polymerisation (GTP) of methyl methacrylate (MMA). Polymerisation reactions could be performed at room temperature by generation of related free NHCs by a simple solvation effect. Catalytic efficiencies of imidazolium-2-carboxylates were found to be approximately three times higher than that of their hydrogen carbonate counterparts for the ROP of D,L-LA, except in the particular case of 1,3-dicyclohexylbenzimidazolium hydrogen carbonate that exhibited a similar catalytic performance to that of NHC–CO2 adducts. The catalytic efficiencies of free NHCs and NHC precursors were thus in the following order: [NHC(H)][HCO3] < NHC–CO2 adducts ≪ free NHCs. Only NHC–CO2 adducts allowed the catalysis of the GTP of MMA in bulk in a controlled manner, [NHC(H)][HCO3] precursor salts being poorly soluble in the monomer substrate, causing a loss of control of GTP under solvent-less conditions.

Related Literature

Contents list

2021-02-24 Front/Back Matter

DOI: 10.1039/C3PY90035E

Synthesis of 1,4-polybutadiene-g-poly(ethylene oxide) via the macromonomer approach by ROMP

Dao Le, Véronique Montembault, Sagrario Pascual, Floraine Collette, Valérie Héroguez, Laurent Fontaine

2013-01-23 Paper

DOI: 10.1039/C3PY21103G

Poly(3-alkylthiophene) with tuneable regioregularity: synthesis and self-assembling properties

Pieter Willot, Joost Steverlynck, David Moerman, Philippe Leclère, Roberto Lazzaroni, Guy Koeckelberghs

2013-03-05 Communication

DOI: 10.1039/C3PY00236E

Synthesis of new n-type isoindigo copolymers

François Grenier, Jean-Rémi Pouliot, Hsin-Rong Tseng, Alan J. Heeger, Mario Leclerc

2012-12-17 Paper

DOI: 10.1039/C2PY20986A

Contents list

Front/Back Matter

DOI: 10.1039/C3PY90023A

Polymerization behaviors and polymer branching structures in ATRP of monovinyl and divinyl monomers

Hongjun Yang, Xiaoqiang Xue, Bibiao Jiang, Jianhai Chen, Yang Yang, Hongting Pu, Yun Liu, Dongliang Zhang, Lizhi Kong, Guangqun Zhai

2013-04-03 Paper

DOI: 10.1039/C3PY00338H

Vinyl-monomer with lysine side chains for preparing copolymer surfaces with fibrinolytic activity

Zengchao Tang, Dan Li, Xiaoli Liu, Zhaoqiang Wu, Wei Liu, Hong Chen

2012-12-07 Paper

DOI: 10.1039/C2PY20944F

Synthesis of poly(dithienogermole-2,6-diyl)s

Joji Ohshita, Masayuki Miyazaki, Daiki Tanaka, Yasushi Morihara, Yuki Fujita, Yoshihito Kunugi

2013-03-26 Paper

DOI: 10.1039/C3PY00253E

Self-assembly of amphiphilic random co-poly(ionic liquid)s: the effect of anions, molecular weight, and molecular weight distribution

Jiangna Guo, Yinxia Zhou, Lihua Qiu, Chao Yuan, Feng Yan

2013-05-09 Paper

DOI: 10.1039/C3PY00460K

You might also like

Compound Q&A

What is 1-(2,4,6-Trifluorophenyl)ethanol (CAS: 1250113-83-7)?

1-(2,4,6-Trifluorophenyl)ethanol is an organic compound with the CAS number 1250...

1250113-83-71-(2,4,6-Trifluoroph...
Compound Q&A

Is 1-(2,4-Dimethoxybenzyl)-4-(hydroxymethyl)-2-pyrrolidinone (CAS: 919111-34-5) safe?

1-(2,4-Dimethoxybenzyl)-4-(hydroxymethyl)-2-pyrrolidinone (CAS: 919111-34-5) is ...

919111-34-51-(2,4-Dimethoxybenz...
Compound Q&A

What are the physical and chemical properties of (7S,15R)-6β,15-Diacetoxy-7α,20-epoxy-7-hydroxykaura-2,16-dien-1-one (CAS: 51419-51-3)?

(7S,15R)-6β,15-Diacetoxy-7α,20-epoxy-7-hydroxykaura-2,16-dien-1-one is a crystal...

51419-51-3(7S,15R)-6β,15-Diace...
Compound Q&A

What regulatory guidelines apply to rac-ethyl (1r,4r)-4-hydroxycyclohexane-1-carboxylate, trans (CAS: 3618-04-0)?

The compound rac-ethyl (1r,4r)-4-hydroxycyclohexane-1-carboxylate, trans (CAS: 3...

3618-04-0rac-ethyl (1r,4r)-4-...
Compound Q&A

What is the market or research trend for 2-(2,4-Difluorophenoxy)-3-nitropyridine (CAS: 175135-62-3)?

The market for 2-(2,4-Difluorophenoxy)-3-nitropyridine (CAS: 175135-62-3) is cur...

175135-62-32-(2,4-Difluoropheno...
Compound Q&A

What are the main uses of 6-Diazo-5-oxo-L-norleucine (CAS: 157-03-9)?

The main uses of 6-Diazo-5-oxo-L-norleucine (CAS: 157-03-9) include research in ...

157-03-96-Diazo-5-oxo-L-norl...
Compound Q&A

What precautions should be taken when handling 2-Aminoethyl-mono-amide-DOTA-tris(tBu ester) (CAS: 173308-19-5)?

When handling 2-Aminoethyl-mono-amide-DOTA-tris(tBu ester) (CAS: 173308-19-5), i...

173308-19-52-Aminoethyl-mono-am...
Compound Q&A

How is 5-Methylimidazo[1,2-a]pyridine-3-carbaldehyde (CAS: 178488-37-4) typically synthesized?

5-Methylimidazo[1,2-a]pyridine-3-carbaldehyde (CAS: 178488-37-4) can be synthesi...

178488-37-45-Methylimidazo[1,2-...
Compound Q&A

Are there alternatives to 2,4,6-Trihydroxyisophthalaldehyde (CAS: 4396-13-8) in synthesis?

There are alternative reagents that can be used in the synthesis of 2,4,6-Trihyd...

4396-13-82,4,6-Trihydroxyisop...
Compound Q&A

What is (2Z)-3-(5-Fluoro-1H-indol-3-yl)-2-sulfanylacrylic acid (CAS: 179461-52-0)?

(2Z)-3-(5-Fluoro-1H-indol-3-yl)-2-sulfanylacrylic acid is a chemical compound wi...

179461-52-0(2Z)-3-(5-Fluoro-1H-...

Source Journal

Polymer Chemistry

Polymer Chemistry
CiteScore: 8.6
Self-citation Rate: 7.3%
Articles per Year: 457

Polymer Chemistry welcomes submissions in all areas of polymer science that have a strong focus on macromolecular chemistry. Manuscripts may cover a broad range of fields, yet no direct application focus is required.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.