Chelate ionic liquids: synthesis, properties and applications

doi:10.11949/j.issn.0438-1157.20171056

Abstract

Abstract:

Coordination-based ionic liquids (IL) have attracted extensive fascination in past few years, for their exceptional physical properties and potential applications in green separation, catalysis and electrolytes. Among them, chelate ILs are advantageous due to their enhanced multiple-site chelating interactions between metals and ligands. Based on positions of metallic components in molecules, chelate ILs can be divided into four classes, i.e., cation, anion, cation-anion and neutral chelate ILs. The synthesis, physical properties and applications of chelate ILs were reviewed from recent publications. Present issues, challenges and future research directions were also discussed.

Key words: ionic liquids, preparation, thermodynamic properties, catalysis

摘要：

配位型离子液体在过去一段时间内得到了广泛的关注。其中，螯合型离子液体因其存在多个配位点，因而可以通过螯合作用增强金属与配体的相互作用。根据金属在分子中所处的位置，可以将螯合型离子液体分为4种类型：阳离子螯合型离子液体、阴离子螯合型离子液体、阴阳离子螯合型离子液体和中性螯合型离子液体。对近年来报道的螯合型离子液体的合成、物理性质及其应用进行了综述，阐述了其存在的问题、面临的挑战和今后研究的方向。

关键词: 离子液体, 制备, 热力学性质, 催化(作用)

CLC Number:

YAO Jia, WANG Guanqi, CHEN Hang, LI Haoran. Chelate ionic liquids: synthesis, properties and applications[J]. CIESC Journal, 2018, 69(1): 203-217.

姚加, 王冠淇, 陈航, 李浩然. 螯合型离子液体：合成、性质以及应用[J]. 化工学报, 2018, 69(1): 203-217.

References 115

[1]	PLECHKOVA N V, SEDDON K R. Applications of ionic liquids in the chemical industry[J]. J. Chem. Technol. Biotechnol., 2008, 37(1):123-150.
[2]	SEDDON K R. Ionic liquids for clean technology[J]. J. Chem. Technol. Biotechnol., 1997, 68(4):351-356.
[3]	WELTON T. Room-temperature ionic liquids solvents for synthesis and catalysis[J]. Chem. Rev., 1999, 99(8):2071-2083.
[4]	WASSERSCHEID P, WELTON T. Ionic Liquids in Synthesis[M]. New York:Wiley-VCH, 2007.
[5]	HURLEY F H, THOMAS P W. The electrodeposition of aluminum from nonaqueous solutions at room temperature[J]. J. Electrochem. Soc., 1951, 98(5):207-212.
[6]	LEE K M, LEE C K, LIN I J B. A facile synthesis of unusual liquid-crystalline gold(Ⅰ) dicarbene compounds[J]. Angew. Chem. Int. Ed., 1997, 36(17):1850-1852.
[7]	LEE C K, LING M J, LIN I J B. Organic-inorganic hybrids of imidazole complexes of palladium(Ⅱ), copper(Ⅱ) and zinc(Ⅱ). Crystals and liquid crystals[J]. Dalton Trans., 2003, (24):4731-4737.
[8]	LEE C K, HSU K M, TSAI C H, et al. Liquid crystals of silver complexes derived from simple 1-alkylimidazoles[J]. Dalton Trans., 2004, (8):1120-1126.
[9]	HUANG J F, LUO H, DAI S. A new strategy for synthesis of novel classes of room-temperature ionic liquids based on complexation reaction of cations general topics[J]. J. Electrochem. Soc., 2006, 153(2):J9-J13.
[10]	JIANG D E, DAI S. First principles molecular dynamics simulation of a task-specific ionic liquid based on silver-olefin complex:atomistic insights into a separation process[J]. J. Phys. Chem. B, 2008, 112(33):10202-10206.
[11]	HUANG J F, LUO H M, LIANG C D, et al. Advanced liquid membranes based on novel ionic liquids for selective separation of olefin/parafrin via olefin-facilitated transport[J]. Ind. Eng. Chem. Res., 2008, 47(3):881-888.
[12]	BROOKS N R, SCHALTIN S, VAN HECKE K, et al. Copper(Ⅰ)-containing ionic liquids for high-rate electrodeposition[J]. Chem.-Eur. J., 2011, 17(18):5054-5059.
[13]	PRATT H D, ROSE A J, STAIGER C L, et al. Synthesis and characterization of ionic liquids containing copper, manganese, or zinc coordination cations[J]. Dalton Trans., 2011, 40(43):11396-11401.
[14]	NOCKEMANN P, PELLENS M, VAN HECKE K, et al. Cobalt(Ⅱ) complexes of nitrile-functionalized ionic liquids[J]. Chem.-Eur. J., 2010, 16(6):1849-1858.
[15]	BROOKS N R, SCHALTIN S, VAN HECKE K, et al. Heteroleptic silver-containing ionic liquids[J]. Dalton Trans., 2012, 41(23):6902-6905.
[16]	NGUYEN M, NGUYEN L, JEON E, et al. Fe-containing ionic liquids as catalysts for the dimerization of bicycle[2.2.1] hepta-2, 5-diene[J]. J. Catal., 2008, 258(1):5-13.
[17]	YOSHIDA Y, SAITO G Z. Influence of structural variations in 1-alkyl-3-methylimidazolium cation and tetrahalogeno-ferrate(Ⅲ) anion on the physical properties of the paramagnetic ionic liquids[J]. J. Mater. Chem., 2006, 16(13):1254-1262.
[18]	MALLICK B, METLEN A, NIEUWENHUYZEN M, et al. Mercuric ionic liquids:[Cnmim] [HgX3], where n=3, 4 and X=Cl, Br[J]. Inorg. Chem., 2012, 51(1):193-200.
[19]	SCHREITER E R, STEVENS J E, ORTWERTH M F, et al. A room-temperature molten salt prepared from AuCl3 and 1-ethyl-3-methylimidazolium chloride[J]. Inorg. Chem., 1999, 38(17):3935-3937.
[20]	HASAN M, KOZHEVNIKOV I V, SIDDIQUI M R H, et al. Gold compounds as ionic liquids. Synthesis, structures, and thermal properties of N, N'-dialkylimidazolium tetrachloroaurate salts[J]. Inorg. Chem., 1999, 38(25):5637-5641.
[21]	CHEN P Y, LIN M C, SUN I W. Electrodeposition of Cu-Zn alloy from a Lewis acidic ZnCl2-EMIC molten salt[J]. J. Electrochem. Soc., 2000, 147(9):3350-3355.
[22]	LIN M C, CHEN P Y, SUN I W. Electrodeposition of zinc telluride from a zinc chloride-1-ethyl-3-methylimidazolium chloride molten salt[J]. J. Electrochem. Soc., 2001, 148(10):C653-C658.
[23]	CHEN P Y, SUN I W. Electrodeposition of cobalt and zinccobalt alloys from a Lewis acidic zinc chloride-1-ethyl-3-methyl imidazolium chloride molten salt[J]. Electrochim. Acta, 2001, 46(8):1169-1177.
[24]	HUANG J F, SUN I W. Electrochemical study of cadmium in acidic zinc chloride-1-ethyl-3-methylimidazolium chloride ionic liquids[J]. J. Electrochem. Soc., 2002, 149(9):E348-E355.
[25]	HUANG J F, SUN I W. Nonanomalous Electrodeposition of zinc-iron alloys in an acidic zinc chloride-1-ethyl-3-methyl imidazolium chloride ionic liquid[J]. J. Electrochem. Soc., 2004, 151(1):C8-C14.
[26]	PITULA S, MUDRING A V. Synthesis, structure, and physico-optical properties of manganate(Ⅱ)-based ionic liquids[J]. Chem.-Eur. J., 2010, 16(11):3355-3365.
[27]	DEETLEFS M, RAUBENHEIMER H G, ESTERHUYSEN M W. Stoichiometric and catalytic reactions of gold utilizing ionic liquids[J]. Catal. Today, 2002, 72(1/2):29-41.
[28]	DEL SESTO R E, MCCLESKEY T M, BURRELL A K, et al. Structure and magnetic behavior of transition metal based ionic liquids[J]. Chem. Commun., 2008, (4):447-449.
[29]	MIAO C X, WANG J Q, YU B, et al. Synthesis of bimagnetic ionic liquid and application for selective aerobic oxidation of aromatic alcohols under mild conditions[J]. Chem. Commun., 2011, 47(9):2697-2699.
[30]	YOSHIDA Y, MUROI K, OTSUKA A, et al. 1-Ethyl-3-methylimidazolium based ionic liquids containing cyano groups:synthesis, characterization, and crystal structure[J]. Inorg. Chem., 2004, 43(4):1458-1462.
[31]	NOCKEMANN P, THIJS B, POSTELMANS N, et al. Anionic rare-earth thiocyanate complexes as building blocks for low-melting metal-containing ionic liquids[J]. J. Am. Chem. Soc., 2006, 128(42):13658-13659.
[32]	MALLICK B, BALKE B, FELSER C, et al. Dysprosium room-temperature ionic liquids with strong luminescence and response to magnetic fields[J]. Angew. Chem.-Int. Edit., 2008, 47(40):7635-7638.
[33]	WANG K, JIAN F, ZHUANG R. A new ionic liquid comprising lanthanum(Ⅲ) bulk -modified carbon paste electrode:preparation, electrochemistry and electrocatalysis[J]. Dalton Trans., 2009, (23):4532-4537.
[34]	PEPPEL T, KÖCKERLING M. Investigations on a series of ionic liquids containing the[Co(Ⅱ)Br(3)quin]-anion (quin=quinoline)[J]. Cryst. Growth Des., 2011, 11(12):5461-5468.
[35]	WANG K, JIAN F, ZHUANG R. New ionic liquid crystal of N,N'-dialkylbenzimidazolium salt comprising cobalt (Ⅱ) thiocyanate[J]. Soft Mater., 2010, 9(1):32-43.
[36]	ZHUANG R, JIAN F, WANG K. A new binuclear Cd(Ⅱ)-containing ionic liquid:preparation and electrocatalytic activities[J]. J. Organomet. Chem., 2009, 694(22):3614-3618.
[37]	KIM H S, KIM J J, KIM H, et al. Imidazolium zinc tetrahalide-catalyzed coupling reaction of CO2 and ethylene oxide or propylene oxide[J]. J. Catal., 2003, 220(1):44-46.
[38]	PALGUNADI J, KWON O S, LEE H, et al. Ionic liquid-derived zinc tetrahalide complexes:structure and application to the coupling reactions of alkylene oxides and CO2[J]. Catal. Today, 2004, 98(4):511-514.
[39]	ALAN C, SENTMAN S C, ROBERT M W, et al. Silver(Ⅰ)-carbene complexes/ionic liquids:novel N-heterocyclic carbene delivery agents for organocatalytic transformations[J]. J. Org. Chem., 2005, 70(6):2391-2393.
[40]	LEE C K, LEE K M, LIN I J B. Inorganic-organic hybrid lamella of di-and tetranuclear silver-carbene complexes[J]. Organometallics., 2002, 21(1):10-12.
[41]	ABBOTT A P, BARRON J C, RYDER K S, et al. Eutectic-based ionic liquids with metal-containing anions and cations[J]. Chem.-Eur. J., 2007, 13(22):6495-6501.
[42]	GAO Y, TWAMLEY B, SHREEVE J M. The first (ferrocenylmethyl)imidazollum and (ferrocenylmethyl)triazolium room temperature ionic liquids[J]. Inorg. Chem., 2004, 43(11):3406-3412.
[43]	AHMED E, RUCK M. Chemistry of polynuclear transition-metal complexes in ionic liquids[J]. Dalton Trans., 2011, 40(37):9347-9357.
[44]	DAVIS J H. Task-specific ionic liquids[J]. Chem Lett., 2004, 33(9):1072-1077.
[45]	SUN I W, WARD E H, HUSSEY C L, et al. Electrochemistry and spectroelectrochemistry of the hexachloroiridate(Ⅲ) and (Ⅳ) complexes in the basic aluminum chloride-1-methyl-3-ethylimidazolium chloride room-temperature ionic liquid[J]. Inorg. Chem., 1987, 26(13):2140-2143.
[46]	HITCHCOCK P B, SEDDON K R, WELTON T. Hydrogen-bond acceptor abilities of tetrachlorometalate(Ⅱ) complexes in ionic liquids[J]. J. Chem. Soc., Dalton Trans., 1993, (17):2639-2643.
[47]	BOWLAS C J, BRUCE D W, SEDDON K R. Liquid-crystalline ionic liquids[J]. Chem. Commun., 1996, (14):1625-1626.
[48]	HOLBREY J D, SEDDON K R. Ionic liquids[J]. Clean Products and Processes., 1999, 1(4):223-236.
[49]	HAMILL J T, HARDACRE C, NIEUWENHUYZEN M, et al. Comment on the preparation of the ionic liquid 1-ethyl-3-methylimidazolium ethanoate:a unique monomeric, homoleptic pentacoordinate lead ethanoate complex[J]. Chem. Commun., 2000, (19):1929-1930.
[50]	MARTYN J E, SEDDON K R. Ionic liquids. Green solvents for the future[J]. Pure Appl. Chem., 2000, 72(7):1391-1398.
[51]	HARDACRE C, HOLBREY J D, MCCORMAC P B, et al. Crystal and liquid crystalline polymorphism in 1-alkyl-3-methyl imidazolium tetrachloropallad-ate(Ⅱ) salts[J]. J. Mater. Chem., 2001, 11(2):346-350.
[52]	BRADLEY A E, HATTER J E, NIEUWENHUYZEN M, et al. Precipitation of a dioxouranium(VI) species from a room temperature ionic liquid medium[J]. Inorg. Chem., 2002, 41(7):1692-1694.
[53]	BRADLEY A, HARDACRE C, NIEUWENHUYZEN M, et al. A structural and electrochemical investigation of 1-alkyl-3-methylimidazolium salts of the nitratodioxouranate(Ⅵ) anions[{UO2(NO3)2}2(μ4-C2O4)]2-,[UO2(NO3)3]-, and[UO2(NO3)4]2-[J]. Inorg. Chem., 2004, 43(8):2503-2514.
[54]	ESTAGER J, NOCKEMANN P, SEDDON K R, et al. Validation of speciation techniques:a study of chlorozincate(Ⅱ) ionic liquids[J]. Inorg. Chem., 2011, 50(11):5258-5271.
[55]	HITCHCOCK P B, LEWIS R J, WELTON T. Vanadyl complexes in ambient-temperature ionic liquids. The first X-ray crystal structure of a tetrachlorooxovanadate(Ⅳ) salt[J]. Polyhedron, 1993, 12(16):2039-2044.
[56]	DENT A J, LEES A, LEWIS R J, et al. Vanadium chloride and chloride oxide complexes in an ambient-temperature ionic liquid. The first use of bis(trichloromethyl) carbonate as a substitute for phosgene in an inorganic system[J]. J. Chem. Soc. Dalton Trans., 1996, (13):2787-2792.
[57]	BROWN R J C, DYSON P J, ELLIS D J, et al. 1-Butyl-3-methylimidazolium cobalt tetracarbonyl[bmim] [Co(CO)4]:a catalytically active organometallic ionic liquid[J]. Chem. Commun., 2001, (18):1862-1863.
[58]	FARMER V, WELTON T. The oxidation of alcohols in substituted imidazolium ionic liquids using ruthenium catalysts[J]. Green Chem., 2002, 4(2):97-102.
[59]	WELTON T. Ionic liquids in catalysis[J]. Coord. Chem. Rev., 2004, 248(21/22/23/24):2459-2477.
[60]	BULUT S, AB RANI M A, WELTON T, et al. Preparation of[Al(hfip)4]--based ionic liquids with siloxane-functionalized cations and their physical properties in comparison with their[Tf2N]-analogues[J]. ChemPhysChem., 2012, 13(7):1802-1805.
[61]	LEE C K, PENG H H, LIN I J B. Liquid crystals of N,N'-dialkylimidazolium salts comprising palladium(Ⅱ) and copper(Ⅱ) ions[J]. Chem. Mater., 2004, 16(3):530-536.
[62]	LIN I J B, VASAM C S. Metal-containing ionic liquids and ionic liquid crystals based on imidazolium moiety[J]. J. Organomet. Chem., 2005, 690(15):3498-3512.
[63]	ZHONG C, SASAKI T, TADA M, et al. Ni ion-containing ionic liquid salt and Ni ion-containing immobilized ionic liquid on silica:application to Suzuki cross-coupling reactions between chloroarenes and arylboronic acids[J]. J. Catal., 2006, 242(1):357-364.
[64]	PINTO A C, LAPIS A A M, DA SILVA B V, et al. Pronounced ionic liquid effect in the synthesis of biologically active isatin-3-oxime derivatives under acid catalysis[J]. Tetrahedron Lett., 2008, 49(39):5639-5641.
[65]	BICA K, GAERTNER P. Metal-containing ionic liquids as efficient catalysts for hydroxymethylation in water[J]. Eur. J. Org. Chem., 2008, (20):3453-3456.
[66]	CERVERA J L S, KONIG A. Recycling concept for aluminum electrodeposition from the ionic liquid system EMIM[Tf2N]-AlCl3[J]. Chem. Eng. Technol., 2010, 33(12):1979-1988.
[67]	SUNDERMEYER W. Fused salts and their use as reaction media[J]. Angew. Chem., Int. Ed., 1965, 4(3):222-238.
[68]	WASSERSCHEID P, KEIM W. Ionic liquids-new "solutions" for transition metal catalysis[J]. Angew. Chem., Int. Ed., 2000, 39(21):3772-3789.
[69]	DUPONT J, DE SOUZA R F, SUAREZ P A Z. Ionic liquid (molten salt) phase organometallic catalysis[J]. Chem. Rev., 2002, 102(10):3667-3692.
[70]	WILKES J S. A short history of ionic liquids-from molten salts to neoteric solvents[J]. Green Chem., 2002, 4(2):73-80.
[71]	LIN H D, LAI C K. Ionic columnar metallomesogens formed by three-coordinated copper(Ⅰ) complexes[J]. J. Chem. Soc., Dalton Trans., 2001, (16):2383-2387.
[72]	HENDERSON W A, BROOKS N R, BRENNESSEL W W, et al. Triglyme-Li+ cation solvate structures:models for amorphous concentrated liquid and polymer electrolytes (Ⅰ)[J]. Chem. Mater., 2003, 15(24):4679-4684.
[73]	HENDERSON W A, BROOKS N R, YOUNG V G. Tetraglyme-Li+ cation solvate structures:models for amorphous concentrated liquid and polymer electrolytes (Ⅱ)[J]. Chem. Mater., 2003, 15(24):4685-4690.
[74]	PAPPENFUS T M, HENDERSON W A, OWENS B B, et al. Complexes of lithium imide salts with tetraglyme and their polyelectrolyte composite materials[J]. J. Electrochem. Soc., 2004, 151(2):A209-A215.
[75]	ⅡDA M, BABA C, INOUE M, et al. Ionic liquids of bis(alkylethylenediamine)silver(Ⅰ) salts and the formation of silver(0) nanoparticles from the ionic liquid system[J]. Chem.-Eur. J., 2008, 14(16):5047-5056
[76]	TAMURA T, HACHIDA T, YOSHIDA K. New glyme-cyclic imide lithium salt complexes as thermally stable electrolytes for lithium batteries[J]. J. Power Sources, 2010, 195(18):6095-6100.
[77]	TAMURA T, YOSHIDA K, HACHIDA T, et al. Physicochemical properties of glyme-Li salt complexes as a new family of room-temperature ionic liquids[J]. Chem. Lett., 2010, 39(7):753-755.
[78]	WANG C M, GUO Y, ZHU X, et al. Highly efficient CO2 capture by tunable alkanolamine-based ionic liquids with multidentate cation coordination[J]. Chem. Commun., 2012, 48(52):6526-6528.
[79]	FUNASAKO Y, MOCHIDA T, TAKAHASHI K, et al. Vapochromic ionic liquids from metal-chelate complexes exhibiting reversible changes in color, thermal, and magnetic properties[J]. Chem-Eur. J., 2012, 18(38):11929-11936.
[80]	SCHOTTENBERGER H, WURST K, HORVATH U E I, et al. Synthesis and characterization of organometallic imidazolium compounds that include a new organometallic ionic liquid[J]. Dalton Trans., 2003, (22):4275-4281.
[81]	FEI Z F, ZHAO D B, SCOPELLITI R, et al. Organometallic complexes derived from alkyne-functionalized imidazolium salts[J]. Organometallics, 2004, 23(7):1622-1628.
[82]	CORMA A, GARCIA H, LEYVA A. An imidazolium ionic liquid having covalently attached an oxime carbapalladacycle complex as ionophilic heterogeneous catalysts for the Heck and Suzuki-Miyaura cross-coupling[J]. Tetrahedron, 2004, 60(38):8553-8560.
[83]	YOSHIDA Y, TANAKA H, SAITO G, et al. Valence-tautomeric ionic liquid composed of a cobalt bis(dioxolene) complex dianion[J]. Inorg. Chem., 2009, 48(21):9989-9991.
[84]	TANAKA K, ISHIGURO F, CHUJO Y. POSS ionic liquid[J]. J. Am. Chem. Soc., 2010, 132(50):17649-17651.
[85]	ZHANG P F, WANG C M, CHEN Z R, et al. Acetylacetone-metal catalyst modified by pyridinium salt group applied to the NHPI-catalyzed oxidation of cholesteryl acetate[J]. Catal. Sci. Technol., 2011, 1(7):1133-1137.
[86]	BRANCO A, BRANCO L C, PINA F. Electrochromic and magnetic ionic liquids[J]. Chem. Commun., 2011, 47(8):2300-2302.
[87]	ZHANG P F, GONG Y T, LV Y Q, et al. Ionic liquids with metal chelate anions[J]. Chem. Commun., 2012, 48(17):2334-2336.
[88]	NICOLAS A H C, MARC M, JEAN-CLAUDE G. An ionic liquid-supported ruthenium carbene complex:a robust and recyclable catalyst for ring-closing olefin metathesis in ionic liquids[J]. J. Am. Chem. Soc., 2003, 125(31):9248-9249.
[89]	YAO Q, ZHANG Y. Olefin metathesis in the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate using a recyclable Ru catalyst:remarkable effect of a designer ionic tag[J]. Angew. Chem., Int. Ed., 2003, 42(29):3395-3398.
[90]	GELDBACH T J, DYSON P J. A versatile ruthenium precursor for biphasic catalysis and its application in ionic liquid biphasic transfer hydrogenation:conventional vs task-specific catalysts[J]. J. Am. Chem. Soc., 2004, 126(26):8114-8115.
[91]	XIAO J C, TWAMLEY B, SHREEVE J M. An ionic liquid-coordinated palladium complex:a highly efficient and recyclable catalyst for the heck reaction[J]. Org. Lett., 2004, 6(21):3845-3847.
[92]	NOH E K, NA S J, SUJITH S, et al. Two components in a molecule:highly efficient and thermally robust catalytic system for CO2/epoxide copolymerization[J]. J. Am. Chem. Soc., 2007, 129(26):8082-8083.
[93]	TAN R, YIN D, YU N, et al. Ionic liquid-functionalized salen Mn(Ⅲ) complexes as tunable separation catalysts for enantioselective epoxidation of styrene[J]. J. Catal., 2008, 255(2):287-295.
[94]	LOMBARDO M, CHIARUCCI M, TROMBINI C. A recyclable triethylammonium ion-tagged diphenylphosphine palladium complex for the Suzuki-Miyaura reaction in ionic liquids[J]. Green Chem., 2009, 11(4):574-579.
[95]	YUN X, HU X, JIN Z, et al. Copper-salen catalysts modified by ionic compounds for the oxidation of cyclohexene by oxygen[J]. J. Mol. Catal. A:Chem., 2010, 327(1/2):25-31.
[96]	GOODRICH P, HARDACRE C, PAUN C, et al. Asymmetric carbon-carbon bond forming reactions catalyzed by metal(Ⅱ) bis(oxazoline) complexes immobilized using supported ionic liquids[J]. Adv. Synth. Catal., 2011, 353(6):995-1004.
[97]	OELKERS B, SUNDERMEYER J. Sulfonate-tagged 1,4-diazabutadiene (DADS) ligands and their noble-metal complexes-synthesis, characterization and immobilization in ionic liquids[J]. Dalton Trans., 2011, 40(47):12727-12741.
[98]	PAPAGNI A, TROMBINI C, LOMBARDO M, et al. Cross-coupling of 5,11-dibromotetracene catalyzed by a triethylammonium ion tagged diphenylphosphine palladium complex in ionic liquids[J]. Organometallics, 2011, 30(16):4325-4329.
[99]	NOZARY H, PIGUET C, RIVERA J P, et al. Extended rodlike polyaromatic receptors with bent tridentate units complexed to lanthanide metal ions[J]. Inorg. Chem., 2000, 39(23):5286-5298.
[100]	NOZARY H, PIGUET C, RIVERA J P, et al. Aromatic bent-core liquid crystals:an opportunity for introducing terdentate binding units into mesophases[J]. Chem. Mater., 2002, 14(3):1075-1090.
[101]	TERAZZI E, BÉNECH J M, RIVERA J P, et al. Metallomesogens with extended bent tridentate receptors:columnar and cubic mesomorphism tuned by the size of the lanthanide metal ions[J]. Dalton Trans., 2003, (5):769-772.
[102]	RODRIGUEZ P, CABALLERO A, DIAZ-REQUEJO M M, et al. Very efficient, reusable copper catalyst for carbene transfer reactions under biphasic conditions using ionic liquids[J]. Org. Lett., 2006, 8(4):557-560.
[103]	ZHAO D B, FEI Z F, SCOPELLITI R, et al. Synthesis and characterization of ionic liquids incorporating the nitrile functionality[J]. Inorg. Chem., 2004, 43(6):2197-2205.
[104]	HU X, MAO J, SUN Y, et al. Acetylacetone-Fe catalyst modified by imidazole ionic compound and its application in aerobic oxidation of β-isophorone[J]. Catal. Commun., 2009, 10(14):1908-1912.
[105]	HENDERSON W A. Glyme-lithium salt phase behavior[J]. J. Phys. Chem. B, 2006, 110(26):13177-13183.
[106]	FUNASAKO Y, KANESHIGE K, INOKUCHI M, et al. Liquids containing cationic SNS-pincer palladium(Ⅱ) complexes:effects of ancillary ligands on thermal properties and solvent polarities[J]. J. Organomet. Chem., 2015, 797:120-124.
[107]	FUNASAKO Y, NOSHO M, MOCHIDA T. Ionic liquids from copper(Ⅱ) complexes with alkylimidazole-containing tripodal ligands[J]. Dalton Trans., 2013, 42(28):10138-10143.
[108]	TOMINAGA T, UEDA T, MOCHIDA T. Effect of substituents and anions on the phase behavior of Ru(Ⅱ) sandwich complexes:exploring the boundaries between ionic liquids and ionic plastic crystals[J]. Phys. Chem. Chem. Phys., 2017, 19(6):4352-4359.
[109]	PISTOIA G, DEROSSI M, SCROSATI B. Study of the behavior of ethylene carbonate as a nonaqueous battery solvent[J]. J. Electrochem. Soc., 1970, 117(4):500-502
[110]	LIDE D R. CRC Handbook of Chemistry and Physics[M]. 86th ed. Boca Raton:CRC Press, 2005.
[111]	DZYULA S V, BARTSCH R A. Influence of structural variations in 1-alkyl(aralkyl)-3-methylimidazolium hexafluorophosphates and bis(trifluorormethyl-sulfonyl)imides on physical properties of the ionic liquids[C]. Chemphyschem., 2002, 3(2):161-166.
[112]	SHEN M M, CHE S Y, ZHANG Y Y, et al. Effect of the temperature and coordination atom on the physicochemical properties of chelate-based ionic liquids and their binary mixtures with water[J]. J. Chem. Eng. Data, 2014, 59(12):3960-3968.
[113]	SI D W, CHEN K X, YAO J, et al. Structures and electronic properties of lithium chelate-based ionic liquids[J]. J. Phys. Chem. B, 2016, 120(16):3904-3913.
[114]	CHEN H, WANG X Y, YAO J, et al. Elucidating interactions between DMSO and chelate-based ionic liquids[J]. Chemphyschem., 2015, 16(18):3836-3841.
[115]	LAN X, MOCHIDA T, FUNASAKO Y, et al. Thermochromic magnetic ionic liquids from cationic nickel(Ⅱ) complexes exhibiting intramolecular coordination equilibrium[J]. Chem.-Eur. J., 2016, 23(4):823-831.