环糊精单分子或多分子层膜的制备及应用

doi:10.16085/j.issn.1000-6613.2015.04.022

摘要/Abstract

摘要： 环糊精因为其独特的包结和识别性能一直受到极大的关注,将环糊精固定在固体基底表面有利于更好地实现其包结选择性,发挥环糊精的潜在应用性能.本文重点综述了在金、硅及聚合物等固体基底表面组装与制备环糊精单分子或多分子层的方法和机理研究进展,主要包括:Langmuir-Blodgett法,Layer-by-Layer法,化学吸附等方法,并对这些方法进行了评价,比较了其优缺点,简要介绍了这些环糊精分子层的应用状况,且对形成单分子或多分子层膜的作用力进行了详细分析.最后围绕膜从制备到应用方面,对环糊精单分子层或多分子层膜的发展趋势进行了展望,认为对常规方法作出改进及采用更加简单有效的新方法制备性能更加稳定的取向性环糊精单/多分子层膜是未来的重点研究方向.

关键词: 环糊精, 单分子/多分子层, 膜, 表面, 分离

Abstract: For the excellent complex and recognition function,cyclodextrins have attracted wide research interest. In order to utilize these special properties of cyclodextrins more effectively,immobilization of cyclodextrins,with specific orientation,upon solid substrate is necessary in many potential applications. This paper summarizes the common methods to prepare monolayer/multilayers of cyclodextrins on solid substrate,including the Langmuir-Blodgett method,Layer-by-Layer technique,and chemical adsorption. These methods are compared and evaluated. The application situation of these systems is introduced. Finally,based on preparations and applications,the future research directions of cyclodextrins monolayer/multilayers membranes are discussed. Improving routine methods and developing simpler methods will be the key research of this area in the future.

Key words: cyclodextrins, monolayer/multilayers, membrane, surface, separation

中图分类号:

O647.1

黄铁凡, 张林, 陈欢林, 高从堦. 环糊精单分子或多分子层膜的制备及应用[J]. 化工进展, 2015, 34(04): 1029-1036.

HUANG Tiefan, ZHANG Lin, CHEN Huanlin, GAO Congjie. Preparation and applications of cyclodextrins monolayer/multilayers membranes[J]. Chemical Industry and Engineering Progree, 2015, 34(04): 1029-1036.

参考文献

[1] 周玉青,韩萍芳,吕效平. 超声协同交联β-环糊精处理苯酚废水[J]. 化工进展,2014,33(3):758-761.
[2] 毛扬帆,李明春,辛梅华等. O-季铵化改性壳聚糖固载环糊精的制备及其载药性能[J]. 化工进展,2010,29(9):1705-1709.
[3] 周志军,蔡荣锡,张林,等. 含环糊精膜的制备与应用[J]. 化学进展,2007,19:1436-1442.
[4] Zhang L,Li L,Liu N,et al. Pervaporation behavior of PVA membrane containing β-cyclodextrin for separating xylene isomeric mixtures[J]. AIChE J.,2013,59:604-612.
[5] Olejnik P,Gniadek M,Palys B. Layers of polyaniline nanotubes deposited by Langmuir-Blodgett method[J]. J. Phys. Chem. C.,2012,116:10424-10429.
[6] Schalchli A,Benattar J,Tchoreloff P,et al. Structure of a monomolecular layer of amphiphilic cyclodextrins[J]. Langmuir,1993,9:1968-1970.
[7] Alexandre S,Coleman W,Kasselouri A,et al. Scanning force microscopy investigation of amphiphilic cyclodextrin Langmuir-Blodgett films[J]. Thin Solid Films,1996,284:765-768.
[8] Kawabata Y,Matsumoto M,Nakamura T,et al. Langmuir-Blodgett films of amphiphilic cyclodextrins[J]. Thin Solid Films,1988,159:353-358.
[9] Shtykov S,Klimov B,Gorin D,et al. Properties of monomolecular layers and Langmuir-Blodgett films on the basis of β-cyclodextrins with various numbers of alkyl chains[J]. Russ. J. Phys. Chem.,2004,78:1632-1636.
[10] Yashchenok A,Gorin D,Pankin K,et al. Transfer ratio of Langmuir-Blodgett films as an indicator of the single-crystal silicon surface modified by polyionic layers[J]. Semiconductors,2007,41:684-688.
[11] Matsumoto M,Matsuzawa Y,Noguchi S,et al. Structure of hybrid Langmuir-Blodgett films of amphiphilic cyclodextrin and water-soluble azobenzene[J]. Mol. Crys. Liq. Crys.,2004,425:475-482.
[12] Matsuzawa Y,Noguchi S,Sakai H,et al. Hybrid Langmuir and Langmuir-Blodgett films composed of amphiphilic cyclodextrins and hydrophobic azobenzene derivative[J]. Thin Solid Films,2006,510:292-296.
[13] Valli L,Giancane G,Mazzaglia A,et al. Photoresponsive multilayer films by assembling cationic amphiphilic cyclodextrins and anionic porphyrins at the air/water interface[J]. Mater. Chem.,2007,17:1660-1663.
[14] Parazak D,Khan A,Dsouza V,et al. Comparison of host-guest Langmuir-Blodgett multilayer formation by two different amphiphilic cyclodextrins[J]. Langmuir,1996,12:4046-4049.
[15] Le Bras Y,Salle M,Leriche P,et al. Functionalization of the cyclodextrin platform with tetrathiafulvalene units:An efficient access towards redox active Langmuir-Blodgett films[J]. J. Mater. Chem.,1997,7:2393-2396.
[16] Badis M,Van der Heyden A,Heck R,et al. Formation of Langmuir layers and surface modification using new upper-rim fully tethered bipyridinyl or bithiazolyl cyclodextrins and their fluorescent metal complexes[J]. Langmuir,2004,20:5338-5346.
[17] Shtykov S,Kalach A,Pankin K,et al. Use of Langmuir-Blodgett films as modifiers for piezoresonance sensors[J]. J. Anal. Chem.,2007,62:490-493.
[18] Niino H,Miyasaka H,Ouchi A,et al. Photopolymerization in a Langmuir-Blodgett film of an amphiphilic cyclodextrin derivative containing a diacetylene group[J]. Thin Solid Films,1989,179:53-57.
[19] 王天雷,刘梅堂,马鸿文. 层层自组装技术制备类水滑石基新型薄膜材料的研究进展[J]. 化工进展,2013,32(7):1584-1603.
[20] Kusumocahyo S,Sumaru K,Kanamori T,et al. Synthesis and characterization of an ultrathin polyion complex membrane containing β-cyclodextrin for separation of organic isomers[J]. J. Mem. Sci.,2004,230:171-174.
[21] Smith R,Riollano M,Leung A,et al. Layer-by-Layer platform technology for small-molecule delivery[J]. Angew. Chem.,Int. Ed.,2009,48:8974-8977.
[22] Crespo-Biel O,Dordi B,Reinhoudt D,et al. Supramolecular layer-by-layer assembly:Alternating adsorptions of guest- and host-functionalized molecules and particles using multivalent supramolecular interactions[J]. J. Am. Chem. Soc.,2005,127:7594-7600.
[23] Crespo-Biel O,Dordi B,Maury P,et al. Noncovalent nanoarchitectures on surfaces:From 2D to 3D nanostructures[J]. Chem. Mater.,2006,18:2545-2551.
[24] Dorokhin D,Hsu S,Tomczak N,et al. Fabrication and luminescence of designer surface patterns with β-cyclodextrin functionalized quantum dots via multivalent supramolecular coupling[J]. ACS Nano.,2010,4:137-142.
[25] Rojas M,Koniger R,Stoddart J,et al. Supported monolayers containing preformed bindingsites. Synthesis and interfacial binding-properties of a thiolated β-cyclodextrin derivative[J]. J. Am. Chem. Soc.,1995,117:336-343.
[26] Beulen M,Bugler J,Lammerink B,et al. Self-assembled monolayers of heptapodant β-cyclodextrins on gold[J]. Langmuir,1998,14:6424-6429.
[27] Beulen M,Bugler J,de Jong M,et al. Host-guest interactions at self-assembled monolayers of cyclodextrins on gold[J]. Chem.:Eur J.,2000,6:1176-1183.
[28] Qian J,Hentschke R,Knoll W. Superstructures of cyclodextrin derivatives on Au(111):A combined random planting molecular dynamics approach[J]. Langmuir,1997,13:7092-7098.
[29] Mendez-Ardoy A,Steentjes T,Kudemac T,et al. Self-assembled monolayers on gold of β-cyclodextrin adsorbates with different anchoring groups[J]. Langmuir,2014,30:3467-3476.
[30] Domi Y,Yoshinaga Y,Shimazu K. Characterization and optimization of mixed thiol-derivatized β-cyclodextrin/pentanethiol monolayers with high-density guest-accessible cavities[J]. Langmuir,2009,25:8094-8100.
[31] Fernandez I,Araque E,Martinez-Ruiz P,et al. Gold surface patterned with cyclodextrin-based molecular nanopores for electrochemical assay of transglutaminase activity[J]. Electrochem. Comm.,2014,40:13-16.
[32] Maeda Y,Fukuda T,Yamamoto H,et al. Regio- and stereoselective complexation by a self-assembled monolayer of thiolated cyclodextrin on a gold electrode[J]. Langmuir,1997,13:4187-4189.
[33] Endo H,Nakaji-Hirabayashi T,Morokoshi S,et al. Orientational effect of surface-confined cyclodextrin on the inclusion of bisphenols[J]. Langmuir,2005,21:1314-1321.
[34] Ng S,Sun T,Chan H. Chiral discrimination of enantiomers with a self-assembled monolayer of functionalized β-cyclodextrins on Au surfaces[J]. Tetra. Lett.,2002,43:2863-2866.
[35] Domi Y,Ikeura K,Okamura K,et al. Strong inclusion of inorganic anions into β-cyclodextrin immobilized to gold electrode[J]. Langmuir,2011,27:10580-10586.
[36] Fang C,Bandaru N,Ellis A,et al. β-Cyclodextrin decorated nanostructured SERS substrates facilitate selective detection of endocrine disruptor chemicals[J]. Biosens. Bioelectron.,2013,42:632-639.
[37] Jung J,Yi S,Jang H,et al. Facile and oriented antibody immobilization on alpha-cyclodextrin-modified sensors surfaces[J]. Macromolecul. Res.,2013,21:130-133.
[38] Huang J,Feng Z,Yang L,et al. A sensitive and selective non-enzyme cholesterol amperometric biosensor based on host-guest effect of β-cyclodextrin for cholesterol[J],Anal. Methods:UK,2012,4:4264-4268.
[39] Diez P,Piuleac C,Martinez-Ruiz P,et al. Supramolecular immobilization of glucose oxidase on gold coated with cyclodextrin-modified cysteamine core PAMAM G-4 dendron/Pt nanoparticles for mediatorless biosensor design[J]. Anal. Bioanal. Chem.,2013,405:3773-3781.
[40] Onclin S,Mulder A,Huskens J,et al. Molecular printboards:Monolayers of β-cyclodextrins on silicon oxide surfaces[J]. Langmuir,2004,20:5460-5466.
[41] Auletta T,Dordi B,Mulder A,et al. Writing patterns of molecules on molecular printboards[J]. Angew. Chem.,Int. Ed.,2004,43:369-373.
[42] Mulder A,Onclin S,Peter M,et al. Molecular printboards on silicon oxide:Lithographic patterning of cyclodextrin monolayers with multivalent,fluorescent guest molecules[J]. Small,2005,1:242-253.
[43] Tahir M,Lee Y. Immobilisation of β-cyclodextrin on glass:Characterisation and application for cholesterol reduction from milk[J]. Food Chem.,2013,139:475-481.
[44] Tahir M,Kwon C,Jeong D,et al. Cholesterol reduction from milk using β-cyclodextrin immobilized on glass[J],J. Dairy Sci.,2013,96:4191-4196.
[45] Schofield W,Badyal J. Controlled fragrant molecule release from surface-tethered cyclodextrin host-guest inclusion complexes[J]. Acs Appl. Mater. Inter.,2011,3:2051-2056.
[46] Schofield W,Bain C,Badyal J. Cyclodextrin-functionalized hierarchical porous architectures for high-throughput capture and release of organic pollutants from wastewater[J]. Chem. Mater.,2012,24:1645-1653.
[47] Wang Y,Chung T,Wang H. Polyamide-imide membranes with surface immobilized cyclodextrin for butanol isomer separation via pervaporation[J]. AIChE J.,2011,57:1470-1484.
[48] Kiasat A,Zarinderakht N,Sayyahi S. β-Cyclodextrin immobilized onto dowex resin:A unique microvessel and heterogeneous catalyst in nucleophilic substitution reactions[J]. Chin. J. Chem.,2012,30:699-702.
[49] Teng M,Li F,Zhang B,et al. Electrospun cyclodextrin-functionalized mesoporous polyvinyl alcohol/SiO₂ nanofiber membranes as a highly efficient adsorbent for indigo carmine dye[J],Colloid Surface A,2011,385:229-234.