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醚基和醇基功能化的特定离子液体:诱人的性质和应用。

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications.

机构信息

Key Laboratory for Green Chemical Technology of Ministry of Education, School of Chemical Engineering & Technology, Tianjin University, Tianjin 300072, China.

出版信息

Chem Soc Rev. 2012 May 21;41(10):4030-66. doi: 10.1039/c2cs15362a. Epub 2012 Mar 28.

DOI:10.1039/c2cs15362a
PMID:22456483
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3341508/
Abstract

In recent years, the designer nature of ionic liquids (ILs) has driven their exploration and exploitation in countless fields among the physical and chemical sciences. A fair measure of the tremendous attention placed on these fluids has been attributed to their inherent designer nature. And yet, there are relatively few examples of reviews that emphasize this vital aspect in an exhaustive or meaningful way. In this critical review, we systematically survey the physicochemical properties of the collective library of ether- and alcohol-functionalized ILs, highlighting the impact of ionic structure on features such as viscosity, phase behavior/transitions, density, thermostability, electrochemical properties, and polarity (e.g. hydrophilicity, hydrogen bonding capability). In the latter portions of this review, we emphasize the attractive applications of these functionalized ILs across a range of disciplines, including their use as electrolytes or functional fluids for electrochemistry, extractions, biphasic systems, gas separations, carbon capture, carbohydrate dissolution (particularly, the (ligno)celluloses), polymer chemistry, antimicrobial and antielectrostatic agents, organic synthesis, biomolecular stabilization and activation, and nanoscience. Finally, this review discusses anion-functionalized ILs, including sulfur- and oxygen-functionalized analogs, as well as choline-based deep eutectic solvents (DESs), an emerging class of fluids which can be sensibly categorized as semi-molecular cousins to the IL. Finally, the toxicity and biodegradability of ether- and alcohol-functionalized ILs are discussed and cautiously evaluated in light of recent reports. By carefully summarizing literature examples on the properties and applications of oxy-functional designer ILs up till now, it is our intent that this review offers a barometer for gauging future advances in the field as well as a trigger to spur further contemplation of these seemingly inexhaustible and--relative to their potential--virtually untouched fluids. It is abundantly clear that these remarkable fluidic materials are here to stay, just as certain design rules are slowly beginning to emerge. However, in fairness, serendipity also still plays an undeniable role, highlighting the need for both expanded in silico studies and a beacon to attract bright, young researchers to the field (406 references).

摘要

近年来,离子液体(ILs)的设计性质促使它们在物理和化学科学的无数领域中得到了探索和开发。这些流体引起了极大的关注,这在一定程度上归因于它们固有的设计性质。然而,相对较少有强调这一重要方面的综述,且这些综述也没有以详尽或有意义的方式来强调这一重要方面。在这篇批判性综述中,我们系统地调查了醚基和醇基功能化离子液体的集体文库的物理化学性质,强调了离子结构对粘度、相行为/转变、密度、热稳定性、电化学性质和极性(如亲水性、氢键能力)等特征的影响。在这篇综述的后一部分,我们强调了这些功能化 IL 在一系列学科中的有吸引力的应用,包括它们作为电解质或功能性流体在电化学、萃取、两相体系、气体分离、碳捕获、碳水化合物溶解(特别是木质纤维素)、聚合物化学、抗菌和抗静电剂、有机合成、生物分子稳定和激活以及纳米科学中的应用。最后,本综述讨论了阴离子功能化 IL,包括硫和氧功能化类似物,以及胆碱基深共晶溶剂(DES),这是一类新兴的流体,可以合理地归类为 IL 的半分子同类物。最后,根据最近的报告,讨论了醚基和醇基功能化 IL 的毒性和生物降解性,并谨慎地进行了评估。通过仔细总结迄今为止关于含氧功能设计 IL 的性质和应用的文献实例,我们希望本综述能为该领域未来的进展提供一个衡量标准,并激发对这些看似无穷无尽的、相对于它们的潜力而言几乎未被触及的流体的进一步思考。显然,这些非凡的流体材料将继续存在,就像一些确定的设计规则开始逐渐出现一样。然而,公平地说,机遇仍然起着不可否认的作用,这突出了需要进行扩展的计算机研究,并需要一个灯塔来吸引聪明的年轻研究人员进入该领域(406 篇参考文献)。

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2
Highly efficient SO2 capture by dual functionalized ionic liquids through a combination of chemical and physical absorption.通过化学和物理吸收的结合,双官能化离子液体实现高效 SO2 捕获。
Chem Commun (Camb). 2012 Mar 7;48(20):2633-5. doi: 10.1039/c2cc16457d. Epub 2012 Jan 13.
3
Green and inexpensive choline-derived solvents for cellulose decrystallization.
基于休克尔阴离子的新型离子液体和塑性晶体的物理化学性质
Chemistry. 2025 Mar 17;31(16):e202403681. doi: 10.1002/chem.202403681. Epub 2025 Feb 10.
4
Oxoammonium-Catalyzed Ether Oxidation via Hydride Abstraction: Methodology Development and Mechanistic Investigation Using Paramagnetic Relaxation Enhancement NMR.通过氢化物提取实现的氧鎓铵催化的醚氧化反应:使用顺磁弛豫增强核磁共振的方法学开发与机理研究
J Am Chem Soc. 2024 Nov 20;146(46):31420-31432. doi: 10.1021/jacs.4c11760. Epub 2024 Nov 11.
5
Design Principles and Applications of Ionic Liquids for Transdermal Drug Delivery.离子液体用于透皮给药的设计原理及应用。
Adv Sci (Weinh). 2024 Nov;11(43):e2405983. doi: 10.1002/advs.202405983. Epub 2024 Sep 29.
6
Experimental and In Silico Comparative Study of Physicochemical Properties and Antimicrobial Activity of Carboxylate Ionic Liquids.实验与计算机模拟比较研究羧酸酯离子液体的物理化学性质和抗菌活性。
Molecules. 2024 Aug 2;29(15):3668. doi: 10.3390/molecules29153668.
7
Cobalt-Catalyzed Reduction of Aldehydes to Alcohols via the Hydroboration Reaction.钴催化醛通过硼氢化反应还原为醇。
Int J Mol Sci. 2024 Jul 19;25(14):7894. doi: 10.3390/ijms25147894.
8
Planting the Seeds of a Decision Tree for Ionic Liquids: Steric and Electronic Impacts on Melting Points of Triarylphosponium Ionic Liquids.为离子液体构建决策树的基础:空间位阻和电子效应 对三芳基鏻离子液体熔点的影响
J Phys Chem B. 2024 Jun 20;128(24):5895-5907. doi: 10.1021/acs.jpcb.4c02196. Epub 2024 Jun 7.
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Imidazolium-based zwitterionic liquid-modified PEG-PLGA nanoparticles as a potential intravenous drug delivery carrier.基于咪唑鎓的两性离子液体修饰的 PEG-PLGA 纳米粒作为一种有潜力的静脉注射药物递送载体。
Nanoscale. 2024 Mar 14;16(11):5584-5600. doi: 10.1039/d3nr06349f.
10
Manipulating Microbial Cell Morphology for the Sustainable Production of Biopolymers.操纵微生物细胞形态以实现生物聚合物的可持续生产
Polymers (Basel). 2024 Feb 1;16(3):410. doi: 10.3390/polym16030410.
用于纤维素脱结晶的绿色且廉价的胆碱衍生溶剂。
Chemistry. 2012 Jan 23;18(4):1043-6. doi: 10.1002/chem.201103271. Epub 2011 Dec 20.
4
Influence of oxygen functionalities on the environmental impact of imidazolium based ionic liquids.氧官能团对基于咪唑鎓的离子液体环境影响的影响。
J Hazard Mater. 2011 Dec 30;198:165-74. doi: 10.1016/j.jhazmat.2011.10.024. Epub 2011 Oct 15.
5
Physicochemical properties of imidazolium-derived ionic liquids with different C-2 substitutions.具有不同 C-2 取代基的咪唑鎓衍生离子液体的物理化学性质。
Phys Chem Chem Phys. 2011 Dec 28;13(48):21503-10. doi: 10.1039/c1cp22375e. Epub 2011 Nov 8.
6
Enhanced stability and activity of cellulase in an ionic liquid and the effect of pretreatment on cellulose hydrolysis.离子液体中纤维素酶的稳定性和活性增强及预处理对纤维素水解的影响。
Biotechnol Bioeng. 2012 Feb;109(2):434-43. doi: 10.1002/bit.23352. Epub 2011 Oct 20.
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Ionic liquids based on diethylmethyl(2-methoxyethyl)ammonium cations and bis(perfluoroalkanesulfonyl)amide anions: influence of anion structure on liquid properties.基于二乙基甲基(2-甲氧基乙基)铵阳离子和双(全氟烷基亚磺酰基)酰胺阴离子的离子液体:阴离子结构对液体性质的影响。
Phys Chem Chem Phys. 2011 Dec 7;13(45):20302-10. doi: 10.1039/c1cp21783f. Epub 2011 Oct 13.
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How ion properties determine the stability of a lipase enzyme in ionic liquids: a molecular dynamics study.离子特性如何决定脂肪酶在离子液体中的稳定性:分子动力学研究。
Phys Chem Chem Phys. 2011 Nov 7;13(41):18647-60. doi: 10.1039/c1cp22056j. Epub 2011 Sep 22.
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Study on hydroxylammonium-based ionic liquids. I. Characterization.基于羟胺的离子液体研究。I. 特性描述。
J Phys Chem B. 2011 Nov 3;115(43):12473-86. doi: 10.1021/jp2062089. Epub 2011 Oct 10.
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Study on hydroxylammonium-based ionic liquids. II. Computational analysis of CO2 absorption.基于羟胺的离子液体研究。II. CO2 吸收的计算分析。
J Phys Chem B. 2011 Nov 3;115(43):12487-98. doi: 10.1021/jp206210e. Epub 2011 Oct 10.