超分子凝胶作为一类新型的智能自组装软材料,从分子水平到微纳米水平的组装过程中,手性发挥了重要的作用.一般情况下,手性信号都是直接从分子转换到纳米纤维中,但也有一些有趣的现象,即混合两种对映体可以调控得到不同手性形态的纤维结构,甚至一些本身不具备手性的构筑块同样可以通过外界诱导得到具有手性结构的组装体.对纤维手性自组装机理的研究不仅揭示了分子手性到纤维微纳米手性转换这一重要过程,而且对新型的手性材料和微纳米器件的开发也有启发作用.有关微纳米水平的手性材料在手性识别、不对称催化、生物大分子结晶和无机材料的手性模板剂、生物医用等领域的应用研究也逐渐得到重视.主要综述了近二十年来有关手性超分子凝胶的研究,主要从凝胶因子的手性自组装、手性在分子水平和微纳米水平上的形貌调控和表征方法、超分子凝胶的手性应用几个方面进行概述,并对手性超分子凝胶的应用和研究前景进行了展望.
参考文献
| [1] | Lara A.Estroff;andrew D.Hamilton .Water Gelation by Small Organic Molecules[J].Chemical Reviews,2004(3):1201-1217. |
| [2] | Beatriu Escuder;Francisco Rodriguez-Llansola;Juan F. Miravet .Supramolecular gels as active media for organic reactions and catalysis[J].New Journal of Chemistry,2010(6):1044-1054. |
| [3] | Lauren E. Buerkle;Stuart J. Rowan .Supramolecular gels formed from multi-component low molecular weight species[J].Chemical Society Reviews,2012(18):6089-6102. |
| [4] | Steed, J.W. .Supramolecular gel chemistry: Developments over the last decade[J].Chemical communications,2011(5):1379-1383. |
| [5] | Parthasarathi Dastidar .Supramolecular gelling agents: can they be designed?[J].Chemical Society Reviews,2008(12):2699-2715. |
| [6] | Chen, X.;Huang, Z.;Chen, S.-Y.;Li, K.;Yu, X.-Q.;Pu, L. .Enantioselective gel collapsing: A new means of visual chiral sensing[J].Journal of the American Chemical Society,2010(21):7297-7299. |
| [7] | Jayawarna, V;Ali, M;Jowitt, TA;Miller, AE;Saiani, A;Gough, JE;Ulijn, RV .Nanostructured hydrogels for three-dimensional cell culture through self-assembly of fluorenylmethoxycarbonyl-dipeptides[J].Advanced Materials,2006(5):611-614. |
| [8] | Xing B;Yu C W;Chow K H.Hydrophobic Interaction and Hydrogen Bonding Cooperatively Confer a Vancomycin Hydrogel: A Potential Candidate for Biomaterials[J].Journal of the American Chemical Society,2002(124):14846-14847. |
| [9] | Khademhosseini A;Langer R .Microengineered hydrogels for tissue engineering.[J].Biomaterials,2007(34):5087-5092. |
| [10] | Altunbas A;Lee SJ;Rajasekaran SA;Schneider JP;Pochan DJ .Encapsulation of curcumin in self-assembling peptide hydrogels as injectable drug delivery vehicles.[J].Biomaterials,2011(25):5906-5914. |
| [11] | Dou, X.;Li, P.;Zhang, D.;Feng, C.-L. .C _2-symmetric benzene-based hydrogels with unique layered structures for controllable organic dye adsorption[J].Soft matter,2012(11):3231-3238. |
| [12] | Kjeld J. C. van Bommel;Arianna Friggeri;Seiji Shinkai .Organic Templates for the Generation of Inorganic Materials[J].Angewandte Chemie International Edition,2003(9):980-999. |
| [13] | Brizard A;Oda R;Hue I.Chirality Effects in Self-assembled Fibrillar Networks[J].Topics in Current Chemistry,2005(256):167-218. |
| [14] | David K. Smith .Lost in translation? Chirality effects in the self-assembly of nanostructured gel-phase materials[J].Chemical Society Reviews,2009(3):684-694. |
| [15] | Wang Y;Xu J;Chen H.Emerging Chirality in Nanoscience[J].ChemSocRev,2012(42):2930-2962. |
| [16] | Frkanec, L;Zinic, M .Chiral bis(amino acid)- and bis(amino alcohol)-oxalamide gelators. Gelation properties, self-assembly motifs and chirality effects[J].Chemical communications,2010(4):522-537. |
| [17] | yoza Kenji;Amanokura Natsuki;Ono Yoshiyuki .Sugar-Integrated Gelators of Organic Solvents-Their Remarkable Diversity in Gelation Ability and Aggregate Structure[J].Chemistry: A European journal,1999(9):2722-2729. |
| [18] | Tomoyuki Koga M M;Nobuyuki Higashi.Structural Control of Self-Assembled Nanofibers by Artificial b-Sheet Peptides Composed of D-or L-Isomer[J].Journal of the American Chemical Society,2005(127):17596-17597. |
| [19] | Maaike de Loos;Jan van Esch;Richard M.Kellogg;Ben L.Feringa .Chiral Recognition in Bis-Urea-Based Aggregates and Organogels through Cooperative Interactions[J].Angewandte Chemie International Edition,2001(3):613-616. |
| [20] | Dzoli Z;Wolsperger K;Zini M.Synergic Effect in Gelation by Two-Component Mixture of Chiral Gelators[J].New Journal of Chemistry,2006(30):1411. |
| [21] | (C)aplar V;(Z)ini(C) M;Pozzo J L.Chiral Gelators Constructed from ll-Aminoundecanoic (AUDA),Lauric and Amino Acid Units.Synthesis,Gelling Properties and Preferred Gelation of Racemates vs.the Pure Enantiomers[J].European Journal of Organic Chemistry,2004(19):4048-4059. |
| [22] | Bose PP;Drew MGB;Das AK;Banerjee A .Formation of triple helical nanofibers using self-assembling chiral benzene-1,3,5-tricarboxamides and reversal of the nanostructure's handedness using mirror image building blocks[J].Chemical communications,2006(30):3196-3198. |
| [23] | A.R.hirst;D.K.smith;M.c.Feiters;H.P.M.Geurts .Two-Component Dendritic Gel:Effect of Stereochemistry on the Supramolecular Chiral Assembly[J].Chemistry: A European journal,2004(23):5901-5910. |
| [24] | Arianna Friggeri;Cornelia van der Pol;Kjeld J.C.van Bommel;Andre Heeres;Marc C.A.Stuart;Ben L.Feringa;Jan van Esch .Cyclohexane-Based Low Molecular Weight Hydrogelators:A Chirality Investigation[J].Chemistry: A European journal,2005(18):5353-5361. |
| [25] | Boettcher C;Schade B;Fuhrhop J H.Comparative Cryo-Electron Microscopy of Noncovalent N-Dodecanoyl-(d-and t-) serine Assemblies in Vitreous Toluene and Water[J].Langmuir,2001(17):873-877. |
| [26] | Lloyd, G.O.;Piepenbrock, M.-O.M.;Foster, J.A.;Clarke, N.;Steed, J.W. .Anion tuning of chiral bis(urea) low molecular weight gels[J].Soft matter,2012(1):204-216. |
| [27] | Koumoto K;Yamashita T;Kimura T.TEM and SEM Observations of Super-Structures Constructed in Organogel Systems From A Combination of Boronic-Acid-Appended Bola-Amphiphiles With Chiral Diols[J].Nanotechnology,2001(12):25. |
| [28] | Svenson S;Messersmith P B.Formation of Polymerizable Phospholipid Nanotubules and Their Transformation into a Network Gel[J].Langmuir,1999(15):4464-4471. |
| [29] | Aurelie Brizard;Carole Aime;Thomas Labrot;Ivan Huc;Damien Berthier;Franck Artzner;Bernard Desbat;Reiko Oda .Counterion, Temperature, and Time Modulation of Nanometric Chiral Ribbons from Gemini-Tartrate Amphiphiles[J].Journal of the American Chemical Society,2007(12):3754-3762. |
| [30] | Adhikari, B.;Nanda, J.;Banerjee, A. .Multicomponent hydrogels from enantiomeric amino acid derivatives: Helical nanofibers, handedness and self-sorting[J].Soft matter,2011(19):8913-8922. |
| [31] | George John;Jong Hwa Jung;Hiroyuki Minamikawa;Kaname Yoshida;Toshimi Shimizu .Morphological Control of Helical Solid Bilayers in High-Axial-Ratio Nanostructures Through Binary Self-Assembly[J].Chemistry: A European journal,2002(23):5494-5500. |
| [32] | Thomas BN.;Clark NA.;Lindemann CM. .Left- and right-handed helical tubule intermediates from a pure chiral phospholipid[J].Physical review.E.Statistical physics, plasmas, fluids, and related interdisciplinary topics,1999(3 Pt.a):3040-3047. |
| [33] | Thomas BN.;Lindemann CM.;Corcoran RC.;Cotant CL.;Kirsch JE. Persichini PJ. .Phosphonate lipid tubules II[J].Journal of the American Chemical Society,2002(7):1227-1233. |
| [34] | Spector MS.;Singh A.;Rodriguez JM.;Price RR.;Schnur JM.;Selinger JV. .Controlling the morphology of chiral lipid tubules[J].Langmuir: The ACS Journal of Surfaces and Colloids,1998(13):3493-3500. |
| [35] | Pakhomov S;Hammer RP;Mishra BK;Thomas BN .Chiral tubule self-assembly from an achiral diynoic lipid.[J].Proceedings of the National Academy of Sciences of the United States of America,2003(6):3040-3042. |
| [36] | Gronwald O.;Shinkai S. .Sugar-integrated gelators of organic solvents[J].Chemistry: A European journal,2001(20):4328-4334. |
| [37] | Fuhrhop J H;Boettcher C.Stereochemistry and Curvature Effects in Supramolecular Organization and Separation Processes of Micellar N-Alkylaldonamide Mixtures[J].Journal of the American Chemical Society,1990(112):1768-1776. |
| [38] | Takuya Nakashima;Nobuo Kimizuka .Light-Harvesting Supramolecular Hydrogels Assembled from Short-Legged Cationic L-Glutamate Derivatives and Anionic Fluorophores[J].Advanced Materials,2002(16):1113-1116. |
| [39] | Lara A. Estroff;Leslie Leiserowitz;Lia Addadi;Steve Weiner;Andrew D. Hamilton .Characterization of an Organic Hydrogel: A Cryo-Transmission Electron Microscopy and X-ray diffraction Study[J].Advanced Materials,2003(1):38-42. |
| [40] | Placin F.;Desvergne JP.;Belin C.;Buffeteau T.;Desbat B.;Ducasse L. Lassegues JC. .Molecular arrangement in the gel fibers of 2,3-didecyloxyanthracene (DDOA): A spectroscopic and theoretical approach[J].Langmuir: The ACS Journal of Surfaces and Colloids,2003(11):4563-4572. |
| [41] | Berthier D.;Buffeteau T.;Leger JM.;Oda R.;Huc I. .From chiral counterions to twisted membranes[J].Journal of the American Chemical Society,2002(45):13486-13494. |
| [42] | Spector M S;Singh A;Messersmith P B.Chiral Self-Assembly of Nanotubules and Ribbons From Phospholipid Mixtures[J].Nano Letters,2001(01):375-378. |
| [43] | Ihara H.;Sakurai T.;Yamada T.;Hashimoto T.;Takafuji M.;Sagawa T. Hachisako H. .Chirality control of self-assembling organogels from a lipophilic L-glutamide derivative with metal chlorides[J].Langmuir: The ACS Journal of Surfaces and Colloids,2002(19):7120-7123. |
| [44] | Gronwald O;Shinkai S .Bifunctional' Sugar-Integrated Gelators for Organic Solvents and Water-On the Role of Nitro-Substituents in l-O-methyl-4,6-O-(Nitro Benzylidene)-Monosaccharides for the Improvement of Gelation Ability[J].Journal of the Chemical Society Perkin Transactions,2001,2(10):1933-1937. |
| [45] | de Loos M;van Esch J;Kellogg R M.Chiral Recognition in Bis-Urea-Based Aggregates and Organogels through Cooperative Interactions[J].Angewandte Chemie International Edition,2001(113):633-636. |
| [46] | Jintoku, H.;Takafuji, M.;Oda, R.;Ihara, H .Enantioselective recognition by a highly ordered porphyrin-assembly on a chiral molecular gel[J].Chemical communications,2012(40):4881-4883. |
| [47] | Jin, Q.;Zhang, L.;Zhu, X.;Duan, P.;Liu, M. .Amphiphilic schiff base organogels: Metal-ion-mediated chiral twists and chiral recognition[J].Chemistry: A European journal,2012(16):4916-4922. |
| [48] | Yoshiyuki Ono;Kazuaki Nakashima;Masahito Sano;Yasumasa Kanekiyo;Kazuhiko Inoue;Junichi Hojo;Seiji Shinkai .Organic gels are useful as a template for the preparation of hollow fiber silica[J].Chemical communications,1998(13):1477-1478. |
| [49] | Yoshivuki Ono K N;Masahito San;Junichi Hojo.Template Effect of Cholesterol-Based Organogels ou Sol-Gel Polymerization Creates Novel Silica with A Helical Structure[J].Chemistry Letters,1999(10):1119-1120. |
| [50] | Jong Hwa Jung Y O;Seiji Shinkai.Sol-Gel Polycondensatin of Tetraethoxysilane in A Cholesterol-Based Organogel System Results in Chiral Spiral Silica[J].Angewandte Chemie International Edition,2000(39):1862-1865. |
| [51] | Jong Hwa Jung;Hedeki Kobayashi;Mitsutoshi Masuda;Toshimi Shimizu;Seiji Shinkai .Helical Ribbon Aggregate Composed of a Crown-Appended Cholesterol Derivative Which Acts as an Amphiphilic Gelator of Organic Solvents and as a Template for Chiral Silica Transcription[J].Journal of the American Chemical Society,2001(36):8785-8789. |
| [52] | Jong Hwa Jung Y O;Kenji Hanabusa;Shinkai S.Creation of Both Right-Handed and Left-Handed Silica Structures by SolGel Transcription of Organogel Fibers Comprised of Chiral Diaminocyclohexaue[J].Journal of the American Chemical Society,2000(122):5008-5009. |
| [53] | Satoshi Kobayashi K;KNobuhiro Hamasaki H;Shirai M.H Preparation of TiO2 Hollow-Fibers Using Supramolecular Assemblies[J].Chemistry of Materials,2000(12):1523-1525. |
| [54] | Jong Hwa Jung;Hideki Kobayashi;Kjeld J C van Bommel.Creation of Novel Helical Ribbon and Double-Layered Nanotube TiO2 Structures Using an Organogel Template[J].Chemistry of Materials,2002(14):1445-1447. |
| [55] | Joel J.E.Moreau;Luc Vellutini;Michel Wong Chi Man .New Hybrid Organic-Inorganic Solids with Helical Morphology via H-Bond Mediated Sol-Gel Hydrolysis of Silyl Derivatives of Chiral (R,R)- or (S,S)-Diureidocyclohexane[J].Journal of the American Chemical Society,2001(7):1509-1510. |
| [56] | Yonggang Yang;Masahiro Suzuki;Hiroaki Fukui;Hirofusa Shirai;Kenji Hanabusa .Preparation of Helical Mesoporous Silica and Hybrid Silica Nanofibers Using Hydrogelator[J].Chemistry of Materials: A Publication of the American Chemistry Society,2006(5):1324-1329. |
| [57] | Rodriguez-Llansola F;Miravet J F;Escuder B A.Supramolecular Hydrogel as a Reusable Heterogeneous Catalyst for the Direct Aldol Reaction[J].Chemical Communications,2009(47):7303-7305. |
| [58] | Itaru Sato;Kousuke Kadowaki;Hiroki Urabe;Jong Hwa Jung;Yoshiyuki Ono;Seiji Shinkai;Kenso Soai .Highly enantioselective synthesis of organic compound using right- and left-handed helical silica[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2003(4):721-724. |
| [59] | Liang, GL;Yang, ZM;Zhang, RJ;Li, LH;Fan, YJ;Kuang, Y;Gao, Y;Wang, T;Lu, WW;Xu, B .Supramolecular Hydrogel of a D-Amino Acid Dipeptide for Controlled Drug Release in Vivo[J].Langmuir: The ACS Journal of Surfaces and Colloids,2009(15):8419-8422. |
| [60] | Luo Z;Wang S;Zhang S .Fabrication of self-assembling D-form peptide nanofiber scaffold d-EAK16 for rapid hemostasis.[J].Biomaterials,2011(8):2013-2020. |
上一张
下一张
上一张
下一张
计量
- 下载量()
- 访问量()
文章评分
- 您的评分：
-
10%
-
20%
-
30%
-
40%
-
50%