化工学报 ›› 2018, Vol. 69 ›› Issue (1): 203-217.DOI: 10.11949/j.issn.0438-1157.20171056
姚加1, 王冠淇1, 陈航1, 李浩然1,2
收稿日期:
2017-08-08
修回日期:
2017-09-20
出版日期:
2018-01-05
发布日期:
2018-01-05
通讯作者:
李浩然
基金资助:
国家自然科学基金项目(21573196,J1210042);浙江科技创新团队项目(2011R50007);国家高技术研究发展计划项目(SS2015AA020601);中央高校基本科研业务费专项资金项目。
YAO Jia1, WANG Guanqi1, CHEN Hang1, LI Haoran1,2
Received:
2017-08-08
Revised:
2017-09-20
Online:
2018-01-05
Published:
2018-01-05
Contact:
10.11949/j.issn.0438-1157.20171056
Supported by:
supported by the National Natural Science Foundation of China (21573196, J1210042), the Program for Zhejiang Leading Team of S&T Innovation (2011R50007), the National High Technology Research and Development Program of China (SS2015AA020601) and the Fundamental Research Funds for the Central Universities, China.
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。
中图分类号:
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.
YAO Jia, WANG Guanqi, CHEN Hang, LI Haoran. Chelate ionic liquids: synthesis, properties and applications[J]. CIESC Journal, 2018, 69(1): 203-217.
[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. |
[1] | 王琪, 张斌, 张晓昕, 武虎建, 战海涛, 王涛. 氯铝酸-三乙胺离子液体/P2O5催化合成伊索克酸和2-乙基蒽醌[J]. 化工学报, 2023, 74(S1): 245-249. |
[2] | 车睿敏, 郑文秋, 王小宇, 李鑫, 许凤. 基于离子液体的纤维素均相加工研究进展[J]. 化工学报, 2023, 74(9): 3615-3627. |
[3] | 陈美思, 陈威达, 李鑫垚, 李尚予, 吴有庭, 张锋, 张志炳. 硅基离子液体微颗粒强化气体捕集与转化的研究进展[J]. 化工学报, 2023, 74(9): 3628-3639. |
[4] | 程业品, 胡达清, 徐奕莎, 刘华彦, 卢晗锋, 崔国凯. 离子液体基低共熔溶剂在转化CO2中的应用[J]. 化工学报, 2023, 74(9): 3640-3653. |
[5] | 王俐智, 杭钱程, 郑叶玲, 丁延, 陈家继, 叶青, 李进龙. 离子液体萃取剂萃取精馏分离丙酸甲酯+甲醇共沸物[J]. 化工学报, 2023, 74(9): 3731-3741. |
[6] | 陈杰, 林永胜, 肖恺, 杨臣, 邱挺. 胆碱基碱性离子液体催化合成仲丁醇性能研究[J]. 化工学报, 2023, 74(9): 3716-3730. |
[7] | 宋明昊, 赵霏, 刘淑晴, 李国选, 杨声, 雷志刚. 离子液体脱除模拟油中挥发酚的多尺度模拟与研究[J]. 化工学报, 2023, 74(9): 3654-3664. |
[8] | 杨绍旗, 赵淑蘅, 陈伦刚, 王晨光, 胡建军, 周清, 马隆龙. Raney镍-质子型离子液体体系催化木质素平台分子加氢脱氧制备烷烃[J]. 化工学报, 2023, 74(9): 3697-3707. |
[9] | 米泽豪, 花儿. 基于DFT和COSMO-RS理论研究多元胺型离子液体吸收SO2气体[J]. 化工学报, 2023, 74(9): 3681-3696. |
[10] | 陆俊凤, 孙怀宇, 王艳磊, 何宏艳. 离子液体界面极化及其调控氢键性质的分子机理[J]. 化工学报, 2023, 74(9): 3665-3680. |
[11] | 郑佳丽, 李志会, 赵新强, 王延吉. 离子液体催化合成2-氰基呋喃反应动力学研究[J]. 化工学报, 2023, 74(9): 3708-3715. |
[12] | 吴文涛, 褚良永, 张玲洁, 谭伟民, 沈丽明, 暴宁钟. 腰果酚生物基自愈合微胶囊的高效制备工艺研究[J]. 化工学报, 2023, 74(7): 3103-3115. |
[13] | 张缘良, 栾昕奇, 苏伟格, 李畅浩, 赵钟兴, 周利琴, 陈健民, 黄艳, 赵祯霞. 离子液体复合萃取剂选择性萃取尼古丁的研究及DFT计算[J]. 化工学报, 2023, 74(7): 2947-2956. |
[14] | 王志龙, 杨烨, 赵真真, 田涛, 赵桐, 崔亚辉. 搅拌时间和混合顺序对锂离子电池正极浆料分散特性的影响[J]. 化工学报, 2023, 74(7): 3127-3138. |
[15] | 龙臻, 王谨航, 任俊杰, 何勇, 周雪冰, 梁德青. 离子液体协同PVCap抑制天然气水合物生成实验研究[J]. 化工学报, 2023, 74(6): 2639-2646. |
阅读次数 | ||||||
全文 |
|
|||||
摘要 |
|
|||||