4,4'-二叠氮二苯乙烯-2,2-二磺酸钠的应用及发展前景
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摘要
4,4'-二叠氮二苯乙烯-2,2-二磺酸钠(DAS)是一种带有磺酸基团的芳香类双叠氮化合物。分子中的叠氮基既可在Cu(Ⅰ)催化的点击化学反应体系中与端炔基形成三唑结构,也能在紫外辐射条件下于两端生成高活性氮宾自由基并插入聚合物链段。本文简单介绍了DAS参与的点击化学反应,简述了DAS的光化学交联原理及其相较于其他化学交联剂的优点,重点论述了近些年DAS在光刻、电池隔膜、分子印迹、医用材料、药物缓释和离子交换膜等领域相关的研究应用及发展前景。此外,提出将DAS与石墨烯、金属有机框架材料(MOF)、聚电解质及脂肪族聚合物等结合应用;设计与DAS结构相似的新型叠氮类分子;深入地探究光化学反应机理;实现叠氮基团的选择性插入等是未来研究的重要趋势。
4,4'-aiazostilbene-2,2'-disulfonic acid disodium salt(DAS) is an aromatic compound with two azido and sulfonic acid groups. When reacting with terminal alkynyl via Cu(Ⅰ)-catalyzed click chemistry reaction, the azido group produces triazole. Under UV irradiation, it also generates highly active nitrene radicals, which can be easily inserted into polymer chains. In this paper, the click chemistry reaction on DAS is briefly introduced. In addition, the photochemical cross-linking mechanism of DAS and its advantages are demonstrated. The recent applications of DAS in different fields of lithography,separators of batteries, molecular imprinting, medical materials, drug release, ion exchange membranes,and etc., are introduced and its developing prospect is made. Furthermore, combining DAS with graphene,metal organic framework material(MOF), polyelectrolyte, aliphatic polymer, and etc., and designing novel azide molecules similar to DAS are suggested to extend its applications. An outlook of exploring the UV reaction mechanism and the insertion of azide groups through controlling the conditions has been proposed.
4,4'-aiazostilbene-2,2'-disulfonic acid disodium salt(DAS) is an aromatic compound with two azido and sulfonic acid groups. When reacting with terminal alkynyl via Cu(Ⅰ)-catalyzed click chemistry reaction, the azido group produces triazole. Under UV irradiation, it also generates highly active nitrene radicals, which can be easily inserted into polymer chains. In this paper, the click chemistry reaction on DAS is briefly introduced. In addition, the photochemical cross-linking mechanism of DAS and its advantages are demonstrated. The recent applications of DAS in different fields of lithography,separators of batteries, molecular imprinting, medical materials, drug release, ion exchange membranes,and etc., are introduced and its developing prospect is made. Furthermore, combining DAS with graphene,metal organic framework material(MOF), polyelectrolyte, aliphatic polymer, and etc., and designing novel azide molecules similar to DAS are suggested to extend its applications. An outlook of exploring the UV reaction mechanism and the insertion of azide groups through controlling the conditions has been proposed.
引文
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[13] SINGH A, BISOI S, BANERJEE S, et al. Hydroquinone based sulfonated copolytriazoles with enhanced proton conductivity[J].Macromolecular Materials and Engineering, 2017, 302(11):1700208.
[14] SAHA S, BANERJEE S, KOMBER H, et al. Flexible diazide based sulfonated polytriazoles and their proton exchange membrane properties[J]. Macromolecular Chemistry and Physics, 2017, 218(14):1700070.
[15] SAHA S, MUKHERJEE R, SINGH A, et al. Synthesis, characterization and investigation of proton exchange properties of sulfonated polytriazoles from a new semifluorinated diazide[J] Monomer Polymer Engineering and Science, 2017, 57(3):312-323.
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[18] BROMBERG L. Zein-poly(N-isopropylacrylamide)conjugates[J].Journal of Physical Chemistry B, 1997, 101(4):504-507.
[19] BARANAC-STOJANOVIC M, STOJANOVIC M, ALEKSIC J.Theoretical study of azido gauche effect and its origin[J]. New Journal of Chemistry, 2017, 41(11):4644-4661.
[20] TAKAHASHI K, ISHII R, NAKAMURA T, et al. Flexible electronic substrate film fabricated using natural clay and wood components with cross-linking polymer[J]. Advanced Materials, 2017, 29(17):1606512.
[21] LU Q W, HE, Y B, YU Q P. et al. Dendrite-free, high-rate, long-life lithium metal batteries with a 3D cross-linked network polymer electrolyte[J]. Advanced Materials, 2017, 29(13):1604460.
[22] LU Y H, YANG Y, ZHANG T F, et al. Photoprompted hot electrons from bulk cross-linked graphene materials and their efficient catalysis for atmospheric ammonia synthesis[J]. ACS Nano, 2016, 10(11):10507-10515.
[23] BISWAS S, ARIEF I, PANJA S S, et al. Absorption-dominated electromagnetic wave suppressor derived from ferrite-doped crosslinked graphene framework and conducting carbon[J]. ACS Applied Materials&Interfaces, 2017, 9(3):3030-3039.
[24] LEE H, DELLATORE S M, MILLER W M, et al. Mussel-inspired surface chemistry for multifunctional coatings[J]. Science, 2007, 318(5849):426-430.
[25] LIU M Y, ZENG G J, WANG K, et al. Recent developments in polydopamine:an emerging soft matter for surface modification and biomedical applications[J]. Nanoscale, 2016, 8(38):16819-16840.
[26] MILLER D J, DREYER D R, BIELAWSKI C W, et al. Surface modification of water purification membranes[J]. Angew. Chem. Int.Ed. Engl., 2017, 56(17):4662-4711.
[27] SHI W J, CAO L Y, ZHANG H, et al. Surface modification of twodimensional metal-organic layers creates biomimetic catalytic microenvironments for selective oxidation[J]. Angew. Chem. Int. Ed.Engl., 2017, 56(33):9704-9709.
[28] ZHI J H, ZHANG L Z, YANG Y Y, et al. Mechanical durability of superhydrophobic surfaces:the role of surface modification technologies[J]. Applied Surface Science, 2017, 392:286-296.
[29] QIAN Y N, LI L H, SONG Y, et al. Surface modification of nanofibrous matrices via layer-by-layer functionalized silk assembly for mitigating the foreign body reaction[J]. Biomaterials, 2018, 164:22-37.
[30] FU J H, JI J, YUAN W Y, et al. Construction of anti-adhesive and antibacterial multilayer films via layer-by-layer assembly of heparin and chitosan[J]. Biomaterials, 2005, 26(33):6684-6692.
[31] ZHANG X, CHEN H, ZHANG H. Layer-by-layer assembly:from conventional to unconventional methods[J]. Chemical Communications,2007, 14(14):1395-1405.
[32] STUPP S I, PALMER L C. Supramolecular chemistry and selfassembly in organic materials design[J]. Chemistry of Materials, 2014,26(1):507-518.
[33] ZHANG F, JIA Z, SRINIVASAN M P. Application of direct covalent molecular assembly in the fabrication of polyimide ultrathin films[J].Langmuir, 2005, 21(8):3389-3395.
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