化工进展 ›› 2015, Vol. 34 ›› Issue (02): 430-446.DOI: 10.16085/j.issn.1000-6613.2015.02.021
沈海民1, 方红果2, 武宏科1, 纪红兵3, 史鸿鑫1
收稿日期:
2014-06-03
修回日期:
2014-07-08
出版日期:
2015-02-05
发布日期:
2015-02-05
通讯作者:
沈海民(1983-),男,博士,讲师,研究方向为环糊精化学、仿生催化。E-mail:haimshen@zjut.edu.cn
基金资助:
SHEN Haimin1, FANG Hongguo2, WU Hongke1, JI Hongbing3, SHI Hongxin1
Received:
2014-06-03
Revised:
2014-07-08
Online:
2015-02-05
Published:
2015-02-05
摘要: 根据环糊精衍生物分子结构与形态的不同,分类综述了环糊精衍生物(以β-环糊精衍生物为主)的形态及其构筑策略研究进展,包括单取代环糊精衍生物、双取代环糊精衍生物、多取代环糊精衍生物、二聚体环糊精衍生物、多聚体环糊精衍生物和环糊精聚合物(包括固载化环糊精)。指出环糊精衍生物的构筑是基于环糊精构筑各种功能材料的基础与关键,是环糊精母体应用的进一步拓展。基于环糊精构筑各种超分子仿酶,不仅可以充分发挥环糊精结构上的先天优势,也可以实现有机合成反应从有机相到水相的顺利过渡,并提高反应的选择性,对有机合成化学的"绿色化"具有重要的意义,对其他功能材料的构筑也具有重要的参考价值和指导意义。
中图分类号:
沈海民, 方红果, 武宏科, 纪红兵, 史鸿鑫. 环糊精衍生物的分子形态及其构筑策略研究进展[J]. 化工进展, 2015, 34(02): 430-446.
SHEN Haimin, FANG Hongguo, WU Hongke, JI Hongbing, SHI Hongxin. Progress in the molecular morphology of cyclodextrin derivatives and their construction strategy[J]. Chemical Industry and Engineering Progree, 2015, 34(02): 430-446.
[1] Szejtli J. Introduction and general overview of cyclodextrin chemistry[J]. Chemical Reviews,1998,98(5):1743-1753. [2] Sallas F,Darcy R. Amphiphilic cyclodextrins:Advances in synthesis and supramolecular chemistry[J]. European Journal of Organic Chemistry,2008(6):957-969. [3] Flaherty R J,Nshime B,De La Marre M,et al. Cyclodextrins as complexation and extraction agents for pesticides from contaminated soil[J]. Chemosphere,2013,91(7):912-920. [4] Liu H H,Cai X Y,Chen J W. Mathematical model for cyclodextrin alteration of bioavailability of organic pollutants[J]. Environmental Science & Technology,2013,47(11):5835-5842. [5] Sanchez-Trujillo M A,Lacorte S,Villaverde J,et al. Decontamination of polycyclic aromatic hydrocarbons and nonylphenol from sewage sludge using hydroxypropyl-beta-cyclodextrin and evaluation of the toxicity of leachates[J]. Environmental Science and Pollution Research,2014,21(1):507-517. [6] Takahashi K. Organic reactions mediated by cyclodextrins[J]. Chemical Reviews,1998,98(5):2013-2033. [7] 纪红兵,黄丽泉,石东坡,等.β-环糊精超分子催化剂用于液相有机合成[J].有机化学,2008,28(12):2072-2080. [8] Bricout H,Hapiot F,Ponchel A,et al. Cyclodextrins as mass transfer additives in aqueous organometallic catalysis[J]. Current Organic Chemistry,2010,14(13):1296-1307. [9] Kakran M,Sahoo N G,Li L,et al. Dissolution enhancement of artemisinin with beta-cyclodextrin[J]. Chemical & Pharmaceutical Bulletin,2011,59(5):646-652. [10] Dong L N,Liu M,Chen A J,et al. Solubilities of quercetin in three beta-cyclodextrin derivative solutions at different temperatures[J]. Journal of Molecular Liquids,2013,177:204-208. [11] He J,Chipot C,Shao X G,et al. Cyclodextrin-mediated recruitment and delivery of amphotericin B[J]. Journal of Physical Chemistry C, 2013,117(22):11750-11756. [12] Khan A R,Forgo P,Stine K J,et al. Methods for selective modifications of cyclodextrins[J]. Chemical Reviews,1998,98(5):1977-1996. [13] Engeldinger E,Armspach D,Matt D. Capped cyclodextrins[J]. Chemical Reviews,2003,103(11):4147-4173. [14] Bellia F,La Mendola D,Pedone C,et al. Selectively functionalized cyclodextrins and their metal complexes[J]. Chemical Society Reviews,2009,38(9):2756-2781. [15] Dong Z Y,Luo Q,Liu J Q. Artificial enzymes based on supramolecular scaffolds[J]. Chemical Society Reviews,2012,41(23):7890-7908. [16] Martinez A,Mellet C O,Fernandez J M G. Cyclodextrin-based multivalent glycodisplays:Covalent and supramolecular conjugates to assess carbohydrate-protein interactions[J]. Chemical Society Reviews,2013,42(11):4746-4773. [17] 沈海民,纪红兵.环糊精衍生物在液相有机合成中的应用[J].有机化学,2011,31(6):791-803. [18] 沈海民,纪红兵.环糊精衍生物在金属催化有机合成中的应用[J].有机化学,2012,32(6):975-985. [19] 沈海民,纪红兵.β-环糊精衍生物诱导Na2MoO4催化H2O2不对称氧化苯甲硫醚[J].有机化学,2012,32(9):1684-1689. [20] Shen H M,Ji H B. Biomimetic asymmetric aldol reactions catalyzed by proline derivatives attached to beta-cyclodextrin in water[J]. Tetrahedron Letters,2012,53(28):3541-3545. [21] Shen H M,Ji H B. Amino alcohol-modified beta-cyclodextrin inducing biomimetic asymmetric oxidation of thioanisole in water[J]. Carbohydrate Research,2012,354:49-58. [22] Shen H M,Ji H B. Cyclodextrin-[RuCl2(Arene)]2 conjugates:Another way to enhance the enantioselectivity of aromatic ketones reduction by aromatic ligands'volume[J]. Tetrahedron,2013,69(39):8360-8367. [23] Chan W K,Yu W Y,Che C M,et al. A cyclodextrin-modified ketoester for stereoselective epoxidation of alkenes[J]. Journal of Organic Chemistry,2003,68(17):6576-6582. [24] Barr L,Easton C J,Lee K,et al. Metallocyclodextrin catalysts for hydrolysis of phosphate triesters[J]. Tetrahedron Letters,2002,43(43):7797-7800. [25] Masurier N,Estour F,Froment M T,et al. Synthesis of 2-substitutedβ-cyclodextrin derivatives with a hydrolytic activity against the organophosphorylester paraoxon[J]. European Journal of Medicinal Chemistry,2005,40(7):615-623. [26] Hamasaki K,Ueno A. Significant enantioselectivity in alanine ester hydrolysis catalyzed by imidazole attached β-cyclodextrins[J]. Chemistry Letters,1995(9):859-860. [27] Hu S S,Li J Y,Xiang J F,et al. Asymmetric supramolecular primary amine catalysis in aqueous buffer:Connections of selective recognition and asymmetric catalysis[J]. Journal of the American Chemical Society,2010,132(20):7216-7228. [28] Mojr V,Herzig V,Budesinsky M,et al. Flavin-cyclodextrin conjugates as catalysts of enantioselective sulfoxidations with hydrogen peroxide in aqueous media[J]. Chemical Communications,2010,46(40):7599-7601. [29] Mojr V,Budesinsky M,Cibulka R,et al. Alloxazine-cyclodextrin conjugates for organocatalytic enantioselective sulfoxidations[J]. Organic & Biomolecular Chemistry,2011,9(21):7318-7326. [30] Doyaguez E G,Fernandez-Mayoralas A. Proline-cyclodextrin conjugates:Synthesis and evaluation as catalysts for aldol reaction in water[J]. Tetrahedron,2012,68(36):7345-7354. [31] Zhang G F,Luan Y X,Han X W,et al. A palladium complex with functionalized beta-cyclodextrin:A promising catalyst featuring recognition abilities for Suzuki-Miyaura coupling reactions in water[J]. Green Chemistry,2013,15(8):2081-2085. [32] Petter R C,Salek J S,Sikorski C T,et al. Cooperative binding by aggregated mono-6-(alkylamino)-β-cyclodextrins[J]. Journal of the American Chemical Society,1990,112(10):3860-3868. [33] Shen B J,Tong L H,Jin D S. Synthesis and characterization of novel multifunctional host compounds. 1. β-Cyclodextrin derivative bearing diethanolamine moiety[J]. Chinese Chemical Letters,1991,2(3):205-208. [34] Brown S E,Coates J H,Coghlan D R,et al. Synthesis and properties of 6A-amino-6A-deoxy-α-and-β-cyclodextrin[J]. Australian Journal of Chemistry,1993,46(6):953-958. [35] Liu Y,Zhang Y M,Qi A D,et al. Molecular recognition study on a supramolecular system. 10. Inclusion complexation of modified β-cyclodextrins with amino acids:Enhanced enantioselectivity for L/D-Leucine[J]. Journal of Organic Chemistry,1997,62(6):1826-1830. [36] Cotner E S,Smith P J. Phosphotyrosine binding by ammonium-and guanidinium-modified cyclodextrins[J]. Journal of Organic Chemistry,1998,63(5):1737-1739. [37] Liu Y,Han B H.,Li B,et al. Molecular recognition study on supramolecular system. 14. Synthesis of modified cyclodextrins and their inclusion complexation thermodynamics with l-tryptophan and some naphthalene derivatives[J]. Journal of Organic Chemistry,1998,63(5):1444-1454. [38] Liu Y,Han B H,Sun S X,et al. Molecular recognition study on supramolecular systems. 20. Molecular recognition and enantioselectivity of aliphatic alcohols by L-tryptophan-modified β-cyclodextrin[J]. Journal of Organic Chemistry,1999,64(5):1487-1493. [39] Hoshino T,Miyauchi M,Kawaguchi Y,et al. Daisy chain necklace:Tri[2]rotaxane containing cyclodextrins[J]. Journal of the American Chemical Society,2000,122(40):9876-9877. [40] Liu Y,Kang S Z,Zhang H Y. Synthesis of β-cyclodextrin derivative bearing a cyclohexylamino moiety and its inclusion complexation with organic dye molecules[J]. Microchemical Journal,2001,70(2):115-121. [41] Peroche S,Parrot-Lopez H. Novel fluorinated amphiphilic cyclodextrin derivatives:Synthesis of mono-,di-and heptakis-(6-deoxy-6-perfluoroalkylthio)-β-cyclodextrins[J]. Tetrahedron Letters,2003,44(2):241-245. [42] Yoon J,Hong S,Martin K A,et al. A general method for the synthesis of cyclodextrinyl aldehydes and carboxylic acids[J]. Journal of Organic Chemistry,1995,60(9):2792-2795. [43] Carofiglio T,Fornasier R,Gennari G,et al. Synthesis and spectroscopic properties of a water-soluble porphyrin-modified β-cyclodextrin compound[J]. Tetrahedron Letters,1997,38(45):7919-7922. [44] Muderawan I W,Ong T T,Lee T C,et al. A reliable synthesis of 2-and 6-amino-β-cyclodextrin and permethylated-β-cyclodextrin[J]. Tetrahedron Letters,2005,46(46):7905-7907. [45] Park K K,Kim Y S,Lee S Y,et al. Preparation and self-inclusion properties of p-xylylenediamine-modified beta-cyclodextrins:Dependence on the side of modification[J]. Journal of the Chemical Society,Perkin Transactions 2,2001(11):2114-2118. [46] Ortega-Caballero F,Bols M. Cyclodextrin derivatives with cyanohydrin and carboxylate groups as artificial glycosidases[J]. Canadian Journal of Chemistry,2006,84(4):650-658. [47] Marinescu L,Molbach M,Rousseau C,et al. Supramolecular oxidation of anilines using hydrogen peroxide as stoichiometric oxidant[J]. Journal of the American Chemical Society,2005,127(50):17578-17579. [48] Ikeda H,Nihei T,Ueno A. Template-assisted stereoselective photocyclodimerization of 2-anthracenecarboxylic acid by bispyridinio-appended γ-cyclodextrin[J]. Journal of Organic Chemistry,2005,70(4):1237-1242. [49] Yang C,Ke C F,Liang W T,et al. Dual Supramolecular photochirogenesis:Ultimate stereocontrol of photocyclodimerization by a chiral scaffold and confining host[J]. Journal of the American Chemical Society,2011,133(35):13786-13789. [50] Lindback E,Zhou Y,Pedersen C M,et al. Artificial enzymes based on cyclodextrin with phenol as the catalytic group[J]. Tetrahedron Letters, 2012,53(37):5023-5026. [51] Zhou Y,Pedersen C M,Bols M. Artificial enzyme activity from cyclodextrins with cyanohydrins on the secondary rim[J]. Tetrahedron Letters,2013,54(20):2458-2461. [52] Tabushi I,Yamamura K,Nabeshima T. Characterization of regiospecific A,C-and A,D-disulfonate capping of β-cyclodextrin. Capping as an efficient production technique[J]. Journal of the American Chemical Society,1984,106(18):5267-5270. [53] Tabushi I,Kuroda Y,Yamada M,et al. A-(modified B6)-B-[ω-amino(ethylamino)]-β-cyclodextrin as an artificial B6 enzyme for chiral aminotransfer reaction[J]. Journal of the American Chemical Society,1985,107(19):5545-5546. [54] Yuan D Q,Yamada T,Fujita K. Amplification of the reactivity difference between two methylene groups of cyclodextrins via a cap[J]. Chemical Communications,2001,24:2706-2707. [55] Pearce A J,Sinay P. Diisobutylaluminum-promoted regioselective de-O-benzylation of perbenzylated cyclodextrins:A powerful new strategy for the preparation of selectively modified cyclodextrins[J]. Angewandte Chemie International Edition,2000,39(20):3610-3612. [56] Hardlei T,Bols M. Unusual hydrogen-bonding differences in stereoisomeric 6-C-alkylated cyclodextrins[J]. Journal of the Chemical Society,Perkin Transactions 1,2002,24:2880-2885. [57] Suresh P,Pitchumani K. Per-6-amino-β-cyclodextrin catalyzed asymmetric Michael addition of nitromethane and thiols to chalcones in water[J]. Tetrahedron:Asymmetry,2008,19(17):2037-2044. [58] Suresh P,Pitchumani K. Per-6-amino-β-cyclodextrin as an efficient supramolecular ligand and host for Cu(Ⅰ)-catalyzed N-arylation of imidazole with aryl bromides[J]. Journal of Organic Chemistry,2008,73(22):9121-9124. [59] Strimbu L,Liu J,Kaifer A E. Cyclodextrin-capped palladium nanoparticles as catalysts for the Suzuki reaction[J]. Langmuir,2003,19(2):483-485. [60] Reetz M T,Waldvogel S R. β-Cyclodextrin-modified diphosphines as ligands for supramolecular rhodium catalysts[J]. Angewandte Chemie International Edition,1997,36(8):865-867. [61] Wong Y T,Yang C,Ying K C,et al. Synthesis of a novel β-cyclodextrin-functionalized diphosphine ligand and its catalytic properties for asymmetric hydrogenation[J]. Organometallics,2002,21(9):1782-1787. [62] Fenger T H,Bjerre J,Bols M. Cyclodextrin aldehydes are oxidase mimics[J]. Chembiochem,2009,10(15):2494-2503. [63] Becker M M,Ravoo B J. Highly fluorinated cyclodextrins and their host-guest interactions[J]. Chemical Communications,2010,46(24):4369-4371. [64] Badi N,Jarroux N,Guegan P. Synthesis of per-2,3-di-O-heptyl-β and γ-cyclodextrins:A new kind of amphiphilic molecules bearing hydrophobic parts[J]. Tetrahedron Letters,2006,47(50):8925-8927. [65] Ashton P R,Koeniger R,Stoddart J F,et al. Amino acid derivatives of β-cyclodextrin[J]. Journal of Organic Chemistry,1996,61(3):903-908. [66] Roehri-Stoeckel C,Dangles O,Brouillard R. A simple synthesis of a highly water soluble symmetrical β-cyclodextrin derivative[J]. Tetrahedron Letters,1997,38(9):1551-1554. [67] Tastan P,Akkaya E U. A novel cyclodextrin homodimer with dual-mode substrate binding and esterase activity[J]. Journal of Molecular Catalysis A:Chemical,2000,157(1-2):261-263. [68] Dong Z Y,Liu J Q,Mao S Z,et al. Aryl thiol substrate 3-carboxy-4-nitrobenzenethiol strongly stimulating thiol peroxidase activity of glutathione peroxidase mimic 2,2'-ditellurobis(2-deoxy-β-cyclodextrin)[J]. Journal of the American Chemical Society,2004,126(50):16395-16404. [69] Yan J M,Breslow R. An enzyme mimic that hydrolyzes an unactivated ester with catalytic turnover[J]. Tetrahedron Letters,2000,41(13):2059-2062. [70] Tang S P,Zhou Y H,Chen H Y,et al. Ester hydrolysis by a cyclodextrin dimer catalyst with a tridentate N,N',N''-Zinc linking group[J]. Chemistry A:Asian Journal,2009,4(8):1354-1360. [71] Huang X,Liu X M,Luo Q A,et al. Artificial selenoenzymes:Designed and redesigned[J]. Chemical Society Reviews,2011,40(3):1171-1184. [72] Tang S P,Chen S,Wu G F,et al. Ester catalytic hydrolysis by a tridentate N,N',N''-copper bridged cyclodextrin dimer[J]. Inorganic Chemistry Communications,2011,14(1):184-188. [73] Hu P,Liu G F,Ji L N,et al. Efficient promotion of phosphate diester cleavage by a face-to-face cyclodextrin dimer without metal[J]. Chemical Communications,2012,48(44):5515-5517. [74] French R R,Holzer P,Leuenberger M G,et al. A supramolecular enzyme mimic that catalyzes the 15,15'double bond scission of β,β-carotene[J]. Angewandte Chemie International Edition,2000,39(7):1267-1269. [75] Ishimaru Y,Masuda T,Iida T. Synthesis of secondary face-to-face cyclodextrin dimers linked at each 2-position[J]. Tetrahedron Letters,1997,38(21):3743-3744. [76] Liu Y,You C C,Li B. Synthesis and molecular recognition of novel oligo(ethylenediamino) bridged bis(β-cyclodextrin)s and their copper(Ⅱ) complexes:Enhanced molecular binding ability and selectivity by multiple recognition[J]. Chemistry A:European Journal,2001,7(6):1281-1288. [77] Gao H,Wang Y N,Fan Y G,et al. Interactions of some modified mono-and bis-beta-cyclodextrins with bovine serum albumin[J]. Bioorganic and Medicinal Chemistry,2006,14(1):131-137. [78] Tang B,Liang H L,Xu K H,et al. An improved synthesis of disulfides linked β-cyclodextrin dimer and its analytical application for dequalinium chloride determination by spectrofluorimetry[J]. Analytica Chimica Acta,2005,554(1-2):31-36. [79] Yang J,Gabriele B,Belvedere S,et al. Catalytic oxidations of steroid substrates by artificial cytochrome P-450 enzymes[J]. Journal of Organic Chemistry,2002,67(15):5057-5067. [80] Nakajima H,Sakabe Y,Ikeda H,et al. Cyclodextrin trimers as receptors for arranging ester and catalyst at optimized location to achieve enhancement of hydrolytic activity[J]. Bioorganic and Medicinal Chemistry Letters,2004,14(7):1783-1786. [81] Breslow R,Zhang X,Xu R,et al. Selective catalytic oxidation of substrates that bind to metalloporphyrin enzyme mimics carrying two or four cyclodextrin groups and related metallosalens[J]. Journal of the American Chemical Society,1996,118(46):11678-11679. [82] Breslow R,Yan J M,Belvedere S. Catalytic hydroxylation of steroids by cytochrome P-450 mimics. Hydroxylation at C-9 with novel catalysts and steroid substrates[J]. Tetrahedron Letters,2002,43(3):363-365. [83] Sasaki K,Nagasaka M,Kuroda Y. New cyclodextrin dimer and trimer:Formation of biphenyl excimer and their molecular recognition[J]. Chemical Communications,2001(24):2630-2631. [84] Charbonnier F,Humbert T,Marsura A. A convenient one-pot synthesis of cyclam-β-cyclodextrins new ligands[J]. Tetrahedron Letters,1998,39(21):3481-3484. [85] Rawal G K,Zhang P,Ling C C. Controlled synthesis of linear alpha-cyclodextrin oligomers using copper-catalyzed huisgen 1,3-dipolar cycloaddition[J]. Organic Letters,2010,12(13):3096-3099. [86] 童林荟.环糊精化学-基础与应用[M]. 北京:科学出版社,2001. [87] Qiu H B,Yang C,Inoue Y,et al. Supramolecular photochirogenesis with cyclodextrin-silica composite. Enantiodifferentiating photocyclodimerization of 2-anthrancenecarboxylate with mesoporous silica wall-capped γ-cyclodextrin[J]. Organic Letters,2009,11(8):1793-1796. [88] Tudisco C,Oliveri V,Cantarella M,et al. Cyclodextrin anchoring on magnetic Fe3O4 nanoparticles modified with phosphonic linkers[J]. European Journal of Inorganic Chemistry,2012(32):5323-5331. [89] Badruddoza A Z M,Rahman M T,Ghosh S,et al. beta-Cyclodextrin conjugated magnetic,fluorescent silica core-shell nanoparticles for biomedical applications[J]. Carbohydrate Polymers,2013,95(1):449-457. [90] Wang Y Q,Han B H. Cyclodextrin-based porous nanocapsules[J]. Chinese Journal of Chemistry,2013,31(5):569-576. [91] Concheiro A,Alvarez-Lorenzo C. Chemically cross-linked and grafted cyclodextrin hydrogels:From nanostructures to drug-eluting medical devices[J]. Advanced Drug Delivery Reviews,2013,65(9):1188-1203. [92] 沈海民,武宏科,纪红兵,等. β-环糊精-Fe3O4 超分子体系的构筑及其应用研究进展[J]. 有机化学,2014,34(4):630-646. [93] 沈海民,纪红兵,武宏科,等. β-环糊精的固载及其应用最新研究进展[J]. 有机化学,2014,34(8):1549-1572. |
[1] | 赖槐东, 程德书, 王坚, 罗菊香. α-甲基苯乙烯马来酸酐共聚物微球固载β-环糊精的制备及应用[J]. 化工进展, 2023, 42(4): 2038-2046. |
[2] | 王妍, 秦振平, 刘越, 张文海, 郭红霞. 环糊精原位改性MoS2管式陶瓷复合膜的制备及性能[J]. 化工进展, 2023, 42(10): 5373-5380. |
[3] | 杨程瑞雪, 黄琪媛, 冉建速, 崔耘通, 王健健. 磷酸修饰二氧化硅负载钯催化剂用于木质素衍生物高效水相低温加氢脱氧[J]. 化工进展, 2023, 42(10): 5179-5190. |
[4] | 李佩珊, 张梦辰, 李铭杰, 郑文镳, 刘敏超, 谢高艺, 徐晓龙, 刘长宇, 郏建波. 基于二维材料膜构筑纳米流体通道的研究进展[J]. 化工进展, 2022, 41(7): 3745-3757. |
[5] | 许慧华, 石东坡, 吴浩, 尹先清, 郑延成, 陈武, 李赓. β-环糊精对曲拉通X-114紫外光谱抗干扰性能的影响[J]. 化工进展, 2022, 41(4): 2075-2081. |
[6] | 钱科, 邓苗, 乔志军, 方志梅, 屠建飞, 阮殿波. 环糊精基活性炭的制备及其电化学性能[J]. 化工进展, 2022, 41(4): 2000-2006. |
[7] | 冯海涛, 刘晓菊, 张弛, 王艳丽, 马晓燕. 复合固体推进剂用新型二茂铁类燃速催化剂研究进展[J]. 化工进展, 2021, 40(5): 2560-2573. |
[8] | 吴保意, 刘奥林, 张金梅, 李运才. 可溶性硅酸钠盐水溶液对金属腐蚀性分析[J]. 化工进展, 2020, 39(S2): 78-82. |
[9] | 邹联沛, 宋琳, 李小伟, 万雨岚, 李曼, 刘建勇, 欧阳创, 奚慧, 钱光人, 戴晓虎. 湿垃圾组分对厌氧消化抑制作用的研究进展[J]. 化工进展, 2020, 39(S2): 362-371. |
[10] | 罗继永, 张道海, 周密, 田琴, 秦舒浩. PBT/TPU/DOPO-MA阻燃复合材料的制备及性能[J]. 化工进展, 2020, 39(8): 3221-3229. |
[11] | 卞维柏, 潘建明. 选择性吸附提锂材料的研究进展[J]. 化工进展, 2020, 39(6): 2206-2217. |
[12] | 李鹏章, 李爱民, 陈博之, 戴建军, 唐敏. 基于活性污泥呼吸速率的化工废水水质评价方法[J]. 化工进展, 2020, 39(6): 2472-2478. |
[13] | 马思思, 汪祺, 邓雪松, 强荣荣, 郑甜甜, 林立刚. 具有动态属性的聚轮烷在膜领域应用进展[J]. 化工进展, 2020, 39(6): 2115-2124. |
[14] | 李恩田,徐洋,姚培,朱媛媛,张怿涵,朱霞石. β-环糊精协同乙烯基咪唑离子液体脱除溶剂油中的萘[J]. 化工进展, 2020, 39(4): 1321-1328. |
[15] | 郝好, 姚庆鑫, 高远, 谢建军. 酶催化超分子自组装及其在癌症诊疗中的应用研究进展[J]. 化工进展, 2020, 39(11): 4568-4574. |
阅读次数 | ||||||
全文 |
|
|||||
摘要 |
|
|||||
京ICP备12046843号-2;京公网安备 11010102001994号 版权所有 © 《化工进展》编辑部 地址:北京市东城区青年湖南街13号 邮编:100011 电子信箱:hgjz@cip.com.cn 本系统由北京玛格泰克科技发展有限公司设计开发 技术支持:support@magtech.com.cn |