噻吩席夫碱结构中含有富电子的硫杂环和席夫碱特性基团(CN),在加工过程中,还可以引入其他特殊官能团,这使得其具有独特的化学性质和生物性质。同时噻吩席夫碱又是良好的金属有机配体,可与大多数过渡金属离子形成配合物,因此良好的分子可设计性和易加工性,使噻吩席夫碱及其配合物得到广泛应用。介绍了噻吩席夫碱及其配合物的结构特性及制备方法,综述了该类化合物在抑菌活性、抗氧化性、电致变色、分子荧光探针和金属缓蚀剂中的应用进展,并展望了噻吩席夫碱未来的研究方向。
Thiophene Schiff base has unique chemical and biological properties because it contains electron rich S heterocycle and Schiff base characteristic group (CN).At the same time,thiophene Schiff base itself is a good metal organic ligand,which can form complexes with most transition metal ions.Therefore,with good molecular designability and processability,thiophene Schiff base and its complexes have been applied in various fields,which is the focus of the current research on Schiff base compounds.The structural characteristics,preparation and application of thiophene Schiff bases and their complexes were introduced.The research progress of these compounds in antibacterial activity,antioxidant activity,electrochromism,molecular fluorescence probe and metal corrosion inhibitor was mainly described.The application of thiophene Schiff bases in different fields was analyzed and summarized.The future application of thiophene Schiff bases was proposed.Finally,the prospect was put forward.
[1] Da Silva C M,Da Silva D L,Modolo L V,et al.Schiff bases:a short review of their antimicrobial activities[J].Journal of Advanced Research,2011,2(1):1-8.
[2] Tezcan F,Yerlikaya G,Mahmood A,et al.A novel thiophene Schiff base as an efficient corrosion inhibitor for mild steel in 1.0M HCl:electrochemical and quantum chemical studies[J].Journal of Molecular Liquids,2018,269:398-406.
[3] Djamel,Daoud,Tahar,et al.Adsorption and corrosion inhibition of new synthesized thiophene Schiff base on mild steel steel X52 in HCl and H2SO4 solutions[J].2014,79:50-58.
[4] Daoud D,Douadi T,Hamani H,et al.Corrosion inhibition of mild steel by two new S-heterocyclic compounds in 1M HCl:experimental and computational study[J].Corrosion Science,2015,94:21-37.
[5] 陈世亮,刘峥,刘洁.对羧基苯甲醛缩-2-噻吩甲酰腙的合成、结构及量子化学计算[J].应用化学,2013,30(1):54-60.
[6] Khalaf M M,Abd El-Lateef H M.Investigation of anti-corrosive potentials of Cu(Ⅱ)-Schiff base complex assembled on magnetic Fe3O4,Fe3O4/TiO2 and Fe3O4/SiO2 nanocubes on carbon steel pipelines in 3.0M HCl[J].Journal of Molecular Liquids,2020,318:114251.
[7] Aouniti A,Elmsellem H,Tighadouini S,et al.Schiff's base derived from 2-acetyl thiophene as corrosion inhibitor of steel in acidic medium[J].Journal of Taibah University for Science,2016,10(5):774-785.
[8] Singh A K,Thakur S,Pani B,et al.Green synthesis and corrosion inhibition study of 2-amino-N′-((thiophen-2-yl)methy-lene)benzohydrazide[J].New Journal of Chemistry,2018,42(3):2113-2124.
[9] Singh A K,Thakur S,Pani B,et al.2-hydroxy-N′-((thiophene-2-yl)methylene)benzohydrazide:ultrasound-assisted synthesis and corrosion inhibition study[J].ACS Omega,2018,3(4):4695-4705.
[10] Boulguemh I E,Beghidja A,Khattabi L,et al.Monomeric and dimeric copper(Ⅱ) complexes based on bidentate N-(propan-2-ylidene) thiophene carbohydrazide Schiff base ligand:synthesis,structure,magnetic properties,antioxidant and anti-Alzheimer activities[J].Inorganica Chimica Acta,2020,507:119519.
[11] Rathi P,Singh D P.Synthesis,antimicrobial,antioxidant and molecular docking studies of thiophene based macrocyclic Schiff base complexes[J].Journal of Molecular Structure,2015,1100:208-214.
[12] Mustafa Bingöl,Turan N.Schiff base and metal(Ⅱ) complexes containing thiophene-3-carboxylate:synthesis,characterization and antioxidant activities[J].Journal of Molecular Structure,2020,1205:127542.
[13] 杨健国,潘富友,李钧敏.Cu-(Ⅱ)2′-(2-噻吩亚甲基)水杨酰腙Schiff碱配合物的合成、表征、晶体结构及抑菌活性研究[J].无机化学学报,2005,21(10):1593-1596.
[14] Mesbah M,Douadi T,Sahli F,et al.Synthesis,characterization,spectroscopic studies and antimicrobial activity of three new Schiff bases derived from heterocyclic moiety[J].Journal of Molecular Structure,2018,1151:41-48.
[15] 杨小兰,钟国清,梁凯.含噻吩双水杨醛席夫碱化合物的合成与抑菌活性[J].精细化工,2013,30(12):1399-1402;1434.
[16] 朱守记,王小淑,徐士超,等.3-对?烯-1-胺及其席夫碱衍生物的抑菌活性研究[J].生物质化学工程,2019,53(4):45-49.
[17] Shanty A A,Mohanan P V.Heterocyclic Schiff bases as non toxic antioxidants:solvent effect,structure activity relationship and mechanism of action[J].Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy,2018,192:181-187.
[18] Hammud H H,El Shazly S,Sonji G,et al.Thiophene aldehyde-diamino uracil Schiff base:a novel fluorescent probe for detection and quantification of cupric,silver and ferric ions[J].Spectrochim Acta A Mol Biomol Spectrosc,2015,150:94-103.
[19] Tiwari K,Mishra M,Singh V P.A highly sensitive and selective fluorescent sensor for Al3+ ions based on thiophene-2-carboxylic acid hydrazide Schiff base[J].RSC Advances,2013,3(30):12124-12132.
[20] Chemchem M,Yahaya I,Aydiner B,et al.A novel and synthetically facile coumarin-thiophene-derived Schiff base for selective fluorescent detection of cyanide anions in aqueous solution:synthesis,anion interactions,theoretical study and DNA-binding properties[J].Tetrahedron,2018,74(48):6897-6906.
[21] Zhang J,Liu Z,Han G C,et al.Inhibition of copper corrosion by the formation of Schiff base self-assembled monolayers[J].Applied Surface Science,2016,389(15):601-608.
[22] Abd El Wanees S,Seda S H.Corrosion inhibition of zinc in aqueous acidic media using a novel synthesized Schiff base-an experimental and theoretical study[J].Journal of Dispersion Science and Technology,2019,40(12):1813-1826.
[23] Issaadi S,Douadi T,Zouaoui A,et al.Novel thiophene symmetrical Schiff base compounds as corrosion inhibitor for mild steel in acidic media[J].Corrosion Science,2011,53(4):1484-1488.
[24] Benmahammed I,Douadi T,Issaadi S,et al.Electrochemical,DFT and MD simulation investigations of the corrosion inhibition properties of heterocyclic sulfide derivatives for mild steel in acidic medium[J].Surface Review and Letters,2020,27(6):127542.
[25] Chao Y C,Chuang C H,Hsu H L,et al.Enhanced thermal stability of organic photovoltaics via incorporating triphenylamine derivatives as additives[J].Solar Energy Materials and Solar Cells,2016,157:666-675.
[26] Wu X,Wang W,Li B,et al.Synthesis and electrochromic,acidochromic properties of Schiff bases containing triphenylamine and thiophene units[J].Spectrochim Acta A Mol Biomol Spectrosc,2015,140:398-406.
[27] Tremblay M H,Skalski T,Gautier Y,et al.Investigation of triphenylamine-thiophene-azomethine derivatives:toward understanding their electrochromic behavior[J].The Journal of Physical Chemistry C,2016,120(17):9081-9087.
[28] 崔普选,魏小平,林达,等.噻吩-2-甲醛缩邻苯二胺敏感膜铬(Ⅲ)离子选择性电极的研制与应用[J].分析测试学报,2009,28(5):585-588.
[29] 杨旸,游毅.含席夫碱的噻吩两亲分子表面活性剂的合成[J].合成化学,2006,14(5):534-535.
[30] 黑嘉慧,杨莉宁,李珺.噻吩醛缩乙二胺席夫碱及其配合物的合成与光催化性能[J].应用化学,2019,36(8):949-957.
[31] Aktas Kamiloglu A,Saka E T,Acar I,et al.Synthesis,characterization,and photocatalytic activity of Co(Ⅱ) and Cu(Ⅱ) phthalocyanines linked with thiophene-Schiff base substituents for 4-nitrophenol oxidation[J].Journal of Coordination Chemistry,2019,72(16):2778-2790.
基金资助
国家自然科学基金(21664009)