1-Allyl-3-vinylimidazolium Chloride: Properties & Uses
1-Allyl-3-vinylimidazolium Chloride: Properties & Uses
1-allyl-3-vinylimidazolium chloride is a dual-olefin-functionalized imidazolium ionic liquid monomer that can undergo free-radical or cross-linking polymerization through both its allyl and vinyl groups, making it a versatile building block for the design of poly(ionic liquid) networks and advanced functional materials.
- Chemical Name
- 1-allyl-3-vinylimidazolium chloride
- CAS Number
- Needs verification — not confirmed in source material
- Molecular Formula
- C8H11ClN2
- Functional Groups
- Allyl group (C=C–C) and vinyl group (C=C) on imidazolium nitrogen atoms
- Ion Type
- Imidazolium-based ionic liquid (cationic monomer, chloride counterion)
- Polymerization Mode
- Free-radical polymerization via allyl and/or vinyl double bonds; capable of cross-linking
- Primary Application Area
- Poly(ionic liquid) synthesis, ion-exchange membranes, stimuli-responsive materials, gel electrolytes
Chemical Structure and Key Properties
1-Allyl-3-vinylimidazolium chloride belongs to the class of imidazolium-based ionic liquid monomers. Its cation carries two distinct polymerizable olefinic arms: an allyl group (–CH2–CH=CH2) on the N-1 nitrogen and a vinyl group (–CH=CH2) on the N-3 nitrogen. The chloride anion acts as the charge-balancing counterion.
As an ionic liquid, the compound is characterized by low volatility, good solvating ability for a range of organic and inorganic species, and inherent ionic conductivity imparted by the mobile chloride anion. The imidazolium ring contributes aromatic stabilization and planarity, influencing both the packing behavior in the solid state and the π-interaction potential with substrates. The dual-olefin design distinguishes this monomer from mono-functional counterparts such as 1-vinylimidazolium or 1-allylimidazolium salts, offering greater architectural flexibility during polymerization.
Note: Exact melting point, density, and spectroscopic data should be confirmed against the certificate of analysis supplied with product SKU A302056.
Synthesis and Handling
Imidazolium chloride monomers of this type are typically prepared by the N-alkylation (quaternization) of a vinyl- or allyl-substituted imidazole precursor. A common synthetic route involves reacting 1-vinylimidazole with allyl chloride under mild heating in the presence of an inert atmosphere, yielding the target quaternary ammonium salt after appropriate purification. Because both substituents contain reactive double bonds, reaction conditions must be carefully controlled to suppress premature polymerization.
Handling precautions:
- Store in a cool, dry place, away from light and heat sources, to prevent spontaneous radical polymerization of the olefinic groups.
- Use appropriate personal protective equipment (nitrile gloves, safety glasses, lab coat) as with all ionic liquid monomers; consult the Safety Data Sheet (SDS) for A302056 before use.
- Inhibitors such as 4-methoxyphenol (MEHQ) may be present; factor this into polymerization protocols when designing initiator concentrations.
- The compound is hygroscopic; handle under inert atmosphere or in a dry environment to minimize water uptake that may affect reproducibility.
Research Applications
The dual polymerizable functionality of 1-allyl-3-vinylimidazolium chloride makes it valuable across several advanced research domains:
Poly(ionic liquid) (PIL) Networks
When both olefinic groups participate in radical polymerization, the monomer acts as a cross-linker, producing three-dimensional PIL networks with tunable mechanical properties and ion-transport characteristics. These networks are studied for use in solid polymer electrolytes and actuators.
Ion-Exchange and Ion-Conductive Membranes
Copolymerization with other ionic or non-ionic monomers yields membranes with adjustable charge density. The chloride counterion can be exchanged post-polymerization (anion metathesis) to introduce hydroxide, bis(trifluoromethanesulfonyl)imide (TFSI), or other functional anions, expanding the application window to alkaline fuel cells and energy-storage devices.
Stimuli-Responsive and Functional Hydrogels
Incorporation of this monomer into hydrogel formulations imparts ionic conductivity and potential responsiveness to ionic-strength or pH changes, relevant to soft robotics, drug delivery matrices, and sensor platforms.
Templating and Nanostructure Fabrication
The amphiphilic character of imidazolium ionic liquids enables self-assembly behavior that researchers exploit to template ordered mesoporous carbons, silica, or metal-organic frameworks when polymerization is conducted in structured media.
Ordering and Specifications
1-Allyl-3-vinylimidazolium chloride is available from Aladdin Scientific under SKU A302056. Researchers are encouraged to:
- Request or download the current Certificate of Analysis (CoA) to confirm purity, lot-specific spectroscopic data, and water content before use in sensitive applications.
- Review the Safety Data Sheet (SDS) for safe handling, storage, and disposal guidance.
- Contact Aladdin Scientific technical support for bulk-quantity inquiries or custom packaging requirements.
- Check the product page for current stock availability, pricing, and compatible reagents for ionic liquid research workflows.
For questions regarding reagent grade, purity specifications, or compatibility with specific polymerization systems, Aladdin Scientific's technical team is available to assist.
Frequently asked questions
What makes 1-allyl-3-vinylimidazolium chloride different from mono-functional ionic liquid monomers?
Unlike mono-functional monomers that carry only one polymerizable double bond and typically form linear polymer chains, 1-allyl-3-vinylimidazolium chloride possesses both an allyl and a vinyl group. This dual functionality allows it to serve simultaneously as a monomer and an internal cross-linker during radical polymerization, enabling the direct formation of three-dimensional poly(ionic liquid) networks without an additional cross-linking reagent.
Can the chloride counterion be exchanged after polymerization?
Yes. Post-polymerization anion exchange (metathesis) is a well-established strategy for poly(ionic liquid) systems. The chloride anion can be replaced by treating the polymer with appropriate metal or ammonium salts carrying the desired anion (e.g., TFSI, BF4⁻, OH⁻), which modifies the ionic conductivity, hydrophilicity, and mechanical properties of the resulting material. The efficiency of anion exchange should be verified by elemental analysis or ion chromatography.
What initiator systems are compatible with polymerization of this monomer?
Free-radical initiators commonly used in aqueous or polar organic media are generally compatible, including thermal initiators such as 2,2′-azobis(2-methylpropionamidine) dihydrochloride (AIBA) and ammonium persulfate, as well as redox couples. If an inhibitor is present in the as-received material, it should be removed or compensated for in the initiator loading. UV-photoinitiators may also be used for photopolymerization applications. Optimal initiator choice should be determined empirically for each formulation.
How should this compound be stored to ensure long-term stability?
The compound should be stored in a tightly sealed container in a cool, dark, and dry location, away from heat sources and direct sunlight. Because it is hygroscopic and contains reactive olefinic groups susceptible to spontaneous radical polymerization, storage under an inert atmosphere (nitrogen or argon) is advisable for long-term preservation. Always check the CoA for specific storage recommendations associated with the particular lot.
Is this monomer suitable for making anion-exchange membranes for fuel cell applications?
Yes, 1-allyl-3-vinylimidazolium chloride is a reported candidate for anion-exchange membrane (AEM) fabrication owing to its cationic imidazolium head group and cross-linkable dual-olefin structure. After polymerization and anion exchange to hydroxide form, the resulting membranes can exhibit hydroxide conductivity suitable for alkaline fuel cell research. Performance metrics such as ionic conductivity, water uptake, and chemical stability should be validated under target operating conditions.
References
- Yuan, J.; Antonietti, M. Poly(ionic liquid)s: Polymers expanding classical property profiles. Polymer 2011, 52, 1469–1482. doi:10.1016/j.polymer.2011.01.043
- Mecerreyes, D. Polymeric ionic liquids: Broadening the properties and applications of polyelectrolytes. Prog. Polym. Sci. 2011, 36, 1629–1648. doi:10.1016/j.progpolymsci.2011.05.007
- Tang, J.; Tang, H.; Sun, W.; Plancher, H.; Radosz, M.; Shen, Y. Poly(ionic liquid)s: a new platform for CO2 capture. Chem. Commun. 2005, 3325–3327. doi:10.1039/b501940k
- Aladdin Scientific. Product Page: 1-allyl-3-vinylimidazolium chloride, SKU A302056. Retrieved 2024.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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