Small molecular ions based ionic self-assembly in preparation of functional supramolecular materials

doi:10.16085/j.issn.1000-6613.2016.08.28

Abstract

Abstract: Ionic self-assembly(ISA)is a powerful tool to create functional supramolecular materials. In this context,the ISA between oppositely charged small molecular ions has attracted enormous attention because of the designable structure and tunable function of small ions. In this paper,the characteristics of ISA technique are briefly introduced,and the developments of small molecular ions based ISA in preparation of functional supramolecular materials are summarized,including the ISA between dye and surfactant,the ISA based on planar charged species and the ISA based on polyoxometallate. So far,great efforts have been made in developing charged building blocks and multi-functional materials. However,there is still a great need in further developing techniques for the practical applications of functional supramolecular materials by the ISA between oppositely charged small molecular ions.

Key words: ionic self-assembly(ISA), small molecular ions, functional supramolecular materials, surfactants, planar charged species

摘要： 离子自组装是合成功能超分子材料的有力途径，而带相反电荷的小分子离子之间的离子自组装由于具有良好的结构可设计性和功能可调节性，是离子自组装制备功能超分子材料领域的研究热点。本文首先对离子自组装的特点进行了简单的介绍，然后分3类对小分子离子自组装制备功能超分子材料领域进行了综述，主要包括染料与表面活性剂自组装制备功能材料，平面刚性离子自组装制备功能材料以及多金属酸盐离子自组装制备功能材料。目前，小分子离子自组装在组装单元的选择以及材料功能扩展角度已取得了长足的进步，但如何实现利用小分子离子自组装从微观结构到宏观材料的跨度，制备出能在实际生产中应用的功能超分子材料，还有待进一步发展。

关键词: 离子自组装, 小分子离子, 功能超分子材料, 表面活性剂, 平面刚性离子

CLC Number:

O641.3
TB34

ZHANG Li, CUI Shangke, ZHOU Qingcheng. Small molecular ions based ionic self-assembly in preparation of functional supramolecular materials[J]. Chemical Industry and Engineering Progree, 2016, 35(08): 2488-2494.

张丽, 崔尚科, 周庆成. 小分子离子自组装制备功能超分子材料[J]. 化工进展, 2016, 35(08): 2488-2494.

References

[1] FAUL C F J,ANTONIETTI M. Ionic self-assembly:facile synthesis of supramolecular materials[J]. Advanced Materials,2003,15(9):673-683.
[2] SCHNEIDER H J. Linear free energy relationships and pairwise interactions in supramolecular chemistry[J]. Chemical Society Reviews,1994,23(4):227-234.
[3] RYBTCHINSKI B. Adaptive supramolecular nanomaterials based on strong noncovalent interactions[J]. ACS Nano,2011,5(9):6791-6818.
[4] FAUL C F. Ionic self-assembly for functional hierarchical nanostructured materials[J]. Accounts of Chemical Research,2014,47(12):3428-3438.
[5] 陈绪猛,陆学民,路庆华. 离子自组装方法在偶氮光响应材料制备中的应用[J]. 化学进展,2010,22(6)1125-1132.
[6] FAUL C F J,ANTONIETTI M. Facile synthesis of optically functional,highly organized nanostructures:dye - surfactant complexes[J]. Chemistry A:European Journal,2002,8(12):2764-2768.
[7] FAUL C F J,ANTONIETTI M,GUAN Y. Ionic self-assembly of dye-surfactant complexes:influence of tail lengths and dye architecture on the phase morphology[J]. Langmuir,2002,18(15):5939-5945.
[8] ZAKREVSKYY Y,STUMPE J,FAUL C F. A supramolecular approach to optically anisotropic materials:photosensitive ionic self-assembly complexes[J]. Advanced Materials,2006,18(16):2133-2136.
[9] ZAKREVSKYY Y,FAUL C,STUMPE J. Film forming photosensitive materials for the light induced generation of optical anisotrophy:WO2006/117403[P]. 2006-11-08.
[10] ZAKREVSKYY Y,FAUL C F,GUAN Y,et al. Alignment of a perylene‐based ionic self‐assembly complex in thermotropic and lyotropic liquid-crystalline phases[J]. Advanced Functional Materials,2004,14(9):835-841.
[11] GUAN Y,ZAKREVSKYY Y,STUMPE J,et al. Perylenediimide-surfactant complexes:thermotropic liquid-crystalline materials via ionic self-assembly[J]. Chemical Communications,2003,7:894-895.
[12] HUANG Y,YAN Y,SMARSLY B M,et al. Helical supramolecular aggregates,mesoscopic organisation and nanofibers of a perylenebisimide-chiral surfactant complex via ionic self-assembly[J]. Journal of Materials Chemistry,2009,19(16):2356-2362.
[13] ECHUE G,LLOYD-JONES G C,FAUL C F J. Chiral perylene diimides:building blocks for ionic self-assembly[J]. Chemistry A:European Journal,2015,21(13):5118-5128.
[14] FU G,WANG M,WANG Y,et al. Ionic self-assembled derivatives of perylenetetracarboxylic dianhydride:facile synthesis,morphology and structures[J]. New Journal of Chemistry,2009,33(4):784-792.
[15] REN X,YU W,ZHANG Z,et al. Gelation and fluorescent organogels of a complex of perylenetetracarboxylic tetraacid with cationic surfactants[J]. Colloids & Surfaces A:Physicochemical & Engineering Aspects,2011,375(1):156-162.
[16] CAMEREL F,ZIESSEL R. Ionic self-assembly of ammonium-based amphiphiles and negatively charged bodipy and porphyrin luminophores[J]. Chemistry A:European Journal,2007,13(8):2189-2200.
[17] ZHANG L,QI H,HAO J,et al. Water-stable,adaptive,and electroactive supramolecular ionic material and its application in biosensing[J]. ACS Applied Materials & Interfaces,2014,6(8):5988-5995.
[18] 张国栋,靳荣华,张在龙. 咪唑类室温离子液体中有序聚集体的组装及应用[J]. 化工进展,2012,31(s1):429-437.
[19] ANDERSON J L,DING R,ELLERN A,et al. Structure and properties of high stability geminal dicationic ionic liquids[J]. Journal of the American Chemical Society,2005,127(2):593-604.
[20] LI Z,HETONG Q,YUEXIANG W,et al. Effective visualization assay for alcohol content sensing and methanol differentiation with solvent stimuli-responsive supramolecular ionic materials[J]. Analytical Chemistry,2014,86(15):7280-7285.
[21] WANG Z,MEDFORTH C J,SHELNUTT J A. Porphyrin nanotubes by ionic self-assembly[J]. Journal of the American Chemical Society,2004,126(49):15954-15955.
[22] OLAYA A J,SCHAMING D,BREVET P F,et al. Self-assembled molecular rafts at liquid|liquid interfaces for four-electron oxygen reduction[J]. Journal of the American Chemical Society,2012,134(1):498-506.
[23] LAUCERI R,FASCIGLIONE G F,D'URSO A,et al. Kinetic investigation of porphyrin interaction with chiral templates reveals unexpected features of the induction and self-propagation mechanism of chiral memory[J]. Journal of the American Chemical Society,2008,130(32):10476-10477.
[24] MARTIN K E,WANG Z,BUSANI T,et al. Donor-Acceptor biomorphs from the ionic self-assembly of porphyrins[J]. Journal of the American Chemical Society,2010,132(23):8194-8201.
[25] 王丽,李巍,刘东志,等. 溶液自组装法制备卟啉纳米材料研究进展 [J]. 化工进展,2013,32(9):2160-2165.
[26] TIAN Y,MARTIN K E,SHELNUTT J Y T,et al. Morphological families of self-assembled porphyrin structures and their photosensitization of hydrogen generation[J]. Chemical Communications,2011,47(21):6069-6071.
[27] WANG Z,HO K J,MEDFORTH C J,et al. Porphyrin nanofiber bundles from phase-transfer ionic self-assembly and their photocatalytic self-metallization[J]. Advanced Materials,2006,18(19):2557-2560.
[28] OZTEK M T,HAMPTON M D,SLATTERY D K,et al. Hydrogen storage with hetero porphyrin aggregates[J]. International Journal of Hydrogen Energy,2011,36(11):6705-6710.
[29] GUAN Y,YU S H,ANTONIETTI M,et al. Synthesis of supramolecular polymers by ionic self-assembly of oppositely charged dyes[J]. Chemistry A:European Journal,2005,11(4):1305-1311.
[30] GRINSTAFF M W,WATHIER M. Synthesis and properties of supramolecular ionic networks[J]. Journal of the American Chemical Society,2008,130(30):9648-9649.
[31] WU D Q,WOJCIECH P,VOLKER E,et al. Controllable columnar organization of positively charged polycyclic aromatic hydrocarbons by choice of counterions[J]. Journal of the American Chemical Society,2009,131(28):9620-9621.
[32] MULLEN K,FENG X,WU D Q. Two-dimensional nanostructures from positively charged polycyclic aromatic hydrocarbons[J]. Angewandte Chemie,2011,123(12):2843-2846.
[33] DONG B,MAEDA H. Ion-based materials comprising planar charged species[J]. Chemical Communications,2013,49(39):4085- 4099.
[34] DONG B,SAKURAI T,BANDO Y,et al. Ion-based materials derived from positively and negatively charged chloride complexes of π-conjugated molecules[J]. Journal of the American Chemical Society,2013,135(39):14797-14805.
[35] DONG B,TERASHIMA Y,HAKETA Y,et al. Charge‐based assemblies comprising planar receptor-anion complexes with bulky alkylammonium cations[J]. Chemistry A:European Journal,2012,18(12):3460-3463.
[36] HAKETA Y,HONSHO Y,SEKI S,et al. Ion materials comprising planar charged species[J]. Chemistry A:European Journal,2012,18(23):7016-7020.
[37] ZHANG T,BROWN J,OAKLEY R J,et al. Towards functional nanostructures:ionic self-assembly of polyoxometalates and surfactants[J]. Current Opinion in Colloid & Interface Science,2009,14(2):62-70.
[38] BU W,WU L,TANG A C. Polyoxometalates matrixed into surfactants:synthesis,characterizations,and conformations of surfactants[J]. Journal of Colloid and Interface Science,2004,269(2):472-475.
[39] SUN H,LI H,BU W,et al. Self-organized microporous structures based on surfactant-encapsulated polyoxometalate complexes[J]. The Journal of Physical Chemistry B,2006,110(49):24847-24854.
[40] BU W,LI H,SUN H,et al. Polyoxometalate-based vesicle and its honeycomb architectures on solid surfaces[J]. Journal of the American Chemical Society,2005,127(22):8016-8017.
[41] LI W,LI H,WU L. Structural characterization of dimethyldioctadecylammonium-encapsulated terbium-substituted heteropolyoxotungatates in solid,Langmuir-Blodgett and solvent-casting films[J]. Colloids and Surfaces A:Physicochemical and Engineering Aspects,2006,272(3):176-181.
[42] ZHANG T,SPITZ C,ANTONIETTI M,et al. Highly photoluminescent polyoxometaloeuropate-surfactant complexes by ionic self-assembly[J]. Chemistry A:European Journal,2005,11(3):1001-1009.
[43] ZHANG T,LIU S,KURTH D G,et al. Organized nanostructured complexes of polyoxometalates and surfactants that exhibit photoluminescence and electrochromism[J]. Advanced Functional Materials,2009,19(4):642-652.
[44] HE T,MA Y,CAO Y,et al. Preparation and electrochromism of alkylammonium molybdate thin films [J]. Journal of Non-Crystalline Solids,2003,315(1):7-12.
[45] ZHANG T R,FENG W,FU Y Q,et al. Self-assembled organic-inorganic composite superlattice thin films incorporating photo-and electro-chemically active phosphomolybdate anion [J]. Journal of Materials Chemistry,2002,12(5):1453-1458.
[46] CHEN Z,LOO B H,MA Y,et al. Photochromism of novel molybdate/alkylamine composite thin films [J]. ChemPhysChem,2004,5(7):1020-1026.
[47] NOGUCHI T,CHIKARA C,KUROIWA K,et al. Controlled morphology and photoreduction characteristics of polyoxometalate(POM)/lipid complexes and the effect of hydrogen bonding at molecular interfaces [J]. Chemical Communications,2011,47(22):6455-6457.
[48] ZHANG J,LI W,WU C,et al. Redox-controlled helical self-assembly of a polyoxometalate Complex[J]. Chemistry A:European Journal,2013,19(25):8129-8135.