双(2-苯并咪唑基)烷烃的合成和应用研究进展
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摘要
近年来,由双(2-苯并咪唑基)烷烃配体构筑的配合物以其多功能性在材料科学等领域引起人们的重视,而作为此类配合物的基础——双(2-苯并咪唑基)烷烃配体的合成与研究已成为人们研究的热点。通过对国内外关于双(2-苯并咪唑基)烷烃配体的传统合成方法和新合成方法的概述,发现其都是以邻苯二胺和脂肪二酸为原料,在不同的催化剂作用下进行的。通过分别对多聚磷酸催化法和微波辐射法的合成原理及存在问题的分析与研究,指出这两种合成方法所存在的不足和需要注意的一些问题。同时,为了更好地将双(2-苯并咪唑基)烷烃应用于生物学、医药、农药等领域,对至今已报道的关于双(2-苯并咪唑基)烷烃配体以及配合物的应用前景进行综述研究。
Recently,bis(2-benzimidazolyl) alkane complex with its versatility in materials science and other fields has drawn increasing attention of scientists.As the basis of the complex,the bis(2-benzimidazolyl) alkane ligand and its' appliaction has become a hot issue.Traditional methods and new methods are summarized at home and abroad so far.The results show that the bis(2-benzimidazolyl) alkane ligand was synthesized from o-phenylenediamine and fatty acid in different catalyst.The synthesis principle of two synthetic methods are analyzed and researched,including polyphosphate catalytic method and microwave radiation method.Then the shortages are also pointed out,and some of the issues that need attention.What's more,this paper outlines the application prospects of the bis(2-benzimidazolyl) alkane ligand and complex have been reported so far.In order to better apply the ligand to areas of biology,pharmaceuticals,and pesticides,to provide a theoretical basis.
Recently,bis(2-benzimidazolyl) alkane complex with its versatility in materials science and other fields has drawn increasing attention of scientists.As the basis of the complex,the bis(2-benzimidazolyl) alkane ligand and its' appliaction has become a hot issue.Traditional methods and new methods are summarized at home and abroad so far.The results show that the bis(2-benzimidazolyl) alkane ligand was synthesized from o-phenylenediamine and fatty acid in different catalyst.The synthesis principle of two synthetic methods are analyzed and researched,including polyphosphate catalytic method and microwave radiation method.Then the shortages are also pointed out,and some of the issues that need attention.What's more,this paper outlines the application prospects of the bis(2-benzimidazolyl) alkane ligand and complex have been reported so far.In order to better apply the ligand to areas of biology,pharmaceuticals,and pesticides,to provide a theoretical basis.
引文
[1]王敏,张一宾.具咪唑基杀菌剂的研究开发进展[J].现代农药,2003,2(1):36-38.
[2]叶佳许,孝良.苯并咪唑衍生物的合成研究进展[J].浙江化工,2012,43(10):21-24.
[3]Craig J M,William C,Sarah L H,et al.Coordination of Zn(II),Cd(II),Hg(II),and Ag(I)by Bis(benzimidazole)Ligands[J].Inorg Chem,1998,37(2):199-207.
[4]Payra P,Hung S C,Kwok W H,et al.Structural,Magnetic and Catalytic Properties of a Self-Recognizedμ-Oxo-Bridged Diiron(III)Bis(benzimidazole)Complex[J].Inorg Chem,2001,40(16):4036-4039.
[5]Robert T S,Maxim V L,Harvey J S,et al.A Geometrically Constraining Bis(benzimidazole)Ligand and Its Nearly Tetrahedral Complexes with Fe(II)and Mn(II)[J].Inorg Chem,2004,43(4):1472-1480.
[6]Nail M S,Rosario S,Frédéric G,et al.Near-Infrared Luminescence of Nine-Coordinate Neodymium Complexes with Benzimidazole-Substituted 8-Hydroxyquinolines[J].Inorg Chem,2008,47(19):9055-9068.
[7]Jiang L,Li Z X,Wang Y,et al.Structures and fluorescence properties of two novel metal-organic frameworks based on the bis(2-benzimidazole)and aromatic carboxylate ligands Inorg Chem Commun,2011,14:1077-1081.
[8]Suman S,Kumar B.Coordination Polymers of Flexible Bis(benzimidazole)Ligand:Halogen Bridging and Metal···Arene Interactions[J].Crystal Growth&Design,2011,11(12):5723-5732.
[9]Liu H Y,Wu H,Yang J,et al.PH-Dependent Assembly of 1D to 3D Octamolybdate Hybrid Materials Based on a New Flexible Bis-[(pyridyl)-benzimidazole]Ligand[J].Cryst Growth Des,2011,11(7):2920-2927.
[10]王卓渊.双苯并咪唑基二氧杂已烷及其配合物的合成、圆二色性和荧光性质[J].四川化工,2012,15(4):32-36.
[11]Feng G D,Jiang L,Li Z X,et al.Coordination polymers with bis(2-benzimidazole)ligand as bridging ligand:From 1D chain to 3D microporous structure[J].Inorg Chem Commun,2012,24:247-253.
[12]Guo Q Q,Xu C Y,Zhao B,et al.Syntheses,Characterizations,and Properties of Five Interpenetrating Complexes Based on1,4-Benzenedicarboxylic Acid and a Series of Benzimidazole-Based Linkers[J].Cryst Growth Des,2012,12(11):5439-5446.
[13]Chen T L,Yu X Y,Zhao X,et al.Syntheses,structures and luminescence properties of two series of 3D lanthanide coordination polymers based onbenzimidazole-5,6-dicarboxylic acid and oxalate[J].Inorg Chem Commun,2012,23:74-77.
[14]张勇,舒威虎,王继猛,等.含苯并咪唑基配体的锌配合物的晶体结构和催化对硝基苯磷酸酯水解的活性研究[J].无机化学学报,2013,29(2):419-423.
[15]Shi Q,Chen L L,Liu D F,et al.A new tetranuclear nickel complex based on the benzimidazole ligand for the controllable polymerization of methyl methacrylate[J].Inorg Chem Commun,2013,29:22-26.
[16]王璐,段冉冉,赵盼,等.含2-氨甲基苯并咪唑铜(Ⅱ)配合物的合成、表征、抑菌活性及与DNA作用的研究[J].华南农业大学学报,2014,35(2):90-95.
[17]刘希慧,卓馨.二(2’-吡啶基)苯并咪唑水合锌配合物的合成和结构表征[J].人工晶体学报,2014,43(1):248-261.
[18]赵越,翟玲玲,孙为银.含苯并咪唑基配体Zn(Ⅱ)、Cd(Ⅱ)配位聚合物的合成、结构以及荧光性质研究[J].无机化学学报,2014,30(1):99-105.
[19]Nail M S,Svetlana V E,Rosario S,et al.Tridentate Benzimidazole-Pyridine-Tetrazolates as Sensitizers of Europium Luminescence[J].Inorg Chem,2014,53(10):171-5178.
[20]Wang X X,Yu M,Li T,et al.A 3D chiral Zn(II)complex based on achiral ligands 2-(1H-imidazolyl-1-methyl)-1H-benzimidazole and adipate[J].Inorg Chem Commun,2014,40:187-189.
[21]Hennigar T L,Macquarrie D C.Supramolecular Isomerism in Coordination Polymers:Conformational Freedom of Ligands in[Co(NO3)2(1,2–bis(4–pyridyl)ethane)1.5]n[J].Angew Chem Int Ed,1997,36:972–973.
[22]Matthews C J,Clegg W,Heath S L,et al.Coordination of Zn(II),Cd(II),Hg(II),and Ag(I)by Bis(benzimidazole)Ligands[J].Inorg Chem,1998,37:199-207.
[23]Yang J,Ma J F,Liu Y Y,et al.Zheng.Four Novel 3D Copper(II)Coordination Polymers with Different Topologies[J].Eur J Inorg Chem,2005:2174-2180.
[24]Tian A X,Ying J,Peng J,et al.Assembly of the Highest Connectivity Wells-Dawson Polyoxometalate Coordination Polymer:The Use of Organic Ligand Flexibility[J].Inorg Chem,2008,47:3274-3283.
[25]Zhou X H,Du X D,Li G N,et al.Coordination Polymers Assembled from 3,5–Pyrazoledicarboxylic Acid and Bis(triazolyl)Ligands:Chiral and Meso–Structures Induced by Ligand Flexibility and a Six–Connected Self–Catenated Network[J].Cryst Growth Des,2009,9:4487-4496.
[26]Huang S L,Hou H W,Mi L W,et al.Enforced 2D supramolecular structures within hydrogen-bonded molecular cocrystals[J].Journal of Coord Chem,2009,62(12):1964-1971.
[27]Tian L,Niu Z,Yang N,et al.Crystal structures and luminescent properties of zinc(II)and cadmium(II)compounds constructed from 5-sulfoisophthalic acid and flexible bis-triazole ligands[J].Inorg Chim Acta,2011,370(1):230-235.
[28]Zhai Q G,Gao X,Li S N,et al.Solvothermal synthesis,crystal structures and photoluminescence properties of the novel Cd/X/α,ω-bis(benzotriazole)alkane hybrid family(X=Cl,Br and I)[J].Cryst Eng Comm,2011,13:1602-1616.
[29]Cao D P,Qin L,Yao X Q,et al.Synthesis,characterization and crystal structure of one Cu(II)complex with flexible tetrapyridine and fatty acid ligand[J].Inorg Chem Commun,2013,29:27-29.
[30]Yang Y T,Cheng F X,Tu C Z,et al.A novel(3,4)-connected Cd(II)-coordination polymer with 3-fold interpenetration assembled from 5-Nitrobenzene-1,2,3-tricarboxylate and flexible 1,6-bis(imidazol-1-yl)-hexane ligands[J].Inorg Chem Commun,2013,29:106-109.
[31]姜娈.双苯并咪唑类配体的合成与应用研究[J].合成材料老化与应用,2011,40(4):41-45.
[32]Shriner R L,Upson R W.Bis-benzimidazoles form dibasic acids[J].J Am Chem Soc,1941,63(8):2277-2278.
[33]Roderick W R,Nordeen C W.Bisbenzimidazoles potent inhibitors of rhinoviruses[J].J Med Chem,1972,15(6):655-658.
[34]胡光耀.双(2-苯并咪唑基)烷烃的合成及结构表征[J].生命科学与医药卫生,2011(2):67-69.
[35]易绣光,聂旭亮,温辉梁.双(2-苯并咪唑基)辛烷的合成及其晶体结构[J].井冈山大学学报:自然科学版,2011,32(2):44-45.
[36]Lane E S.A modified benzimidazole synthesis[J].J Chem Soc,1953,4:2238-2240.
[37]Vyas P C,Oza C K,Goyal A K.A simple synthesis of 2,2’-bis-benzimidazole[J].Chem I nd(London),1980,7:287-288.
[38]宋林清,谭祖干,徐贤伦.微波辐射下双(2-苯并咪唑基)烷烃的合成[J].合成化学,2001,9(2):175-176.
[39]王璐瑶,韩洁,李晓娟,等.双(2-苯并咪唑基)烷烃的简便合成方法[J].化学试剂,2005,27(5):317-320.
[40]吕维忠,刘波,韦少慧,等.微波辐射下双(2-苯并咪唑基)丙烷的合成与结构表征[J].化学研究与应用,2007,19(7):817-819.
[41]戴卫东,李泉,钱礼华.双(2-苯并咪唑基)乙烷的合成工艺研究[J].江西师范大学学报:自然科学版,2009,33(3):275-278.
[42]Hein D W,Alheim R J,Leavitt J J.The Use of Polyphosphoric Acid in the Synthesis of 2-Aryl-and2-Alkyl-substituted Benzimidazoles,Benzoxazoles and Benzothiazoles[J].J Am Chem Soc,1957,79(2):427-429.
[43]Lin S Y,Isome Y,Stewart E,et al.Microware-assisted one step high-throughput synthesis is of benzimidazoles[J].Tetrahedron Letters,2006,47:2883-2886.
[44]Gedyer R,Smith F,Westaway K.The use of microwave ovens for rapid organic synthesis[J].Tetrahedron Lett,1986,27(3):279-282.
[45]Geratz J D,Tidwell R R,Lowbardy R J,et al.Streptococal cell wall-induced systemic disease:Beneficial effects of transbis(5-amidino-2-benzidazolyl)ethene,a novel,macrophage-directed anti-inflammatory agent[J].Am J Pathol,1991,139(4):921-931.
[46]Guo Dong Feng,Luan Jiang,Qiang Chen,et al.A2D Wavy Parquet Architecture Based on the Biphenyl-3,3’,4,4’-tetracarboxylic Acid and Bis(2-benzimidazole)alkanes Ligands[J].Chinese J.Struct.Chem.(Jiegou Huaxue),2013,32(1):45-50.
[47]Zhou Q,Yang P.Crystal structure and DNA-binding studies of a new Cu(II)complex involving benzimidazole[J].Inorg Chim Acta,2006,359:1200-1206.
[48]Zimmer C,Wahnert U.Nonintercalating DNA-binding ligands:Specificity of the interaction and their use as tools in biophysical,biochemical and biological investigation of the genetic material[J].Prog Biophys Mol Biol,1986,47:31-112.
[49]高娟丽.双苯并咪唑类衍生物的合成及其抑菌活性研究[D].咸阳:西北农林科技大学,2012.
[50]段彩明,韩萍扬.N,N’-二(对甲苯磺酞)亚磺酰胺-S-(2-苯并咪唑基)钠在照相乳剂中的超增感应用[J].感光材料,1996(6):19-22.
[51]沈永嘉.苯并咪唑酮颜料及其应用[J].化工科技市场,2001(4):6-11.
[52]赵建喜,王艾戎.咪唑衍生物及其应用[J].绝缘材料,2002(5):36-39.
[53]卢艳华,庞正智,王磊.新型环氧树脂固化剂2-烷基苯并咪唑的研究[J].热固性树脂,2003,18(6):1-3.
[54]浦鸿汀,刘改花.磷酸掺杂新型聚苯并咪唑的质子导电性能的研究[J].功能材料,2005,36(2):217-202.
[2]叶佳许,孝良.苯并咪唑衍生物的合成研究进展[J].浙江化工,2012,43(10):21-24.
[3]Craig J M,William C,Sarah L H,et al.Coordination of Zn(II),Cd(II),Hg(II),and Ag(I)by Bis(benzimidazole)Ligands[J].Inorg Chem,1998,37(2):199-207.
[4]Payra P,Hung S C,Kwok W H,et al.Structural,Magnetic and Catalytic Properties of a Self-Recognizedμ-Oxo-Bridged Diiron(III)Bis(benzimidazole)Complex[J].Inorg Chem,2001,40(16):4036-4039.
[5]Robert T S,Maxim V L,Harvey J S,et al.A Geometrically Constraining Bis(benzimidazole)Ligand and Its Nearly Tetrahedral Complexes with Fe(II)and Mn(II)[J].Inorg Chem,2004,43(4):1472-1480.
[6]Nail M S,Rosario S,Frédéric G,et al.Near-Infrared Luminescence of Nine-Coordinate Neodymium Complexes with Benzimidazole-Substituted 8-Hydroxyquinolines[J].Inorg Chem,2008,47(19):9055-9068.
[7]Jiang L,Li Z X,Wang Y,et al.Structures and fluorescence properties of two novel metal-organic frameworks based on the bis(2-benzimidazole)and aromatic carboxylate ligands Inorg Chem Commun,2011,14:1077-1081.
[8]Suman S,Kumar B.Coordination Polymers of Flexible Bis(benzimidazole)Ligand:Halogen Bridging and Metal···Arene Interactions[J].Crystal Growth&Design,2011,11(12):5723-5732.
[9]Liu H Y,Wu H,Yang J,et al.PH-Dependent Assembly of 1D to 3D Octamolybdate Hybrid Materials Based on a New Flexible Bis-[(pyridyl)-benzimidazole]Ligand[J].Cryst Growth Des,2011,11(7):2920-2927.
[10]王卓渊.双苯并咪唑基二氧杂已烷及其配合物的合成、圆二色性和荧光性质[J].四川化工,2012,15(4):32-36.
[11]Feng G D,Jiang L,Li Z X,et al.Coordination polymers with bis(2-benzimidazole)ligand as bridging ligand:From 1D chain to 3D microporous structure[J].Inorg Chem Commun,2012,24:247-253.
[12]Guo Q Q,Xu C Y,Zhao B,et al.Syntheses,Characterizations,and Properties of Five Interpenetrating Complexes Based on1,4-Benzenedicarboxylic Acid and a Series of Benzimidazole-Based Linkers[J].Cryst Growth Des,2012,12(11):5439-5446.
[13]Chen T L,Yu X Y,Zhao X,et al.Syntheses,structures and luminescence properties of two series of 3D lanthanide coordination polymers based onbenzimidazole-5,6-dicarboxylic acid and oxalate[J].Inorg Chem Commun,2012,23:74-77.
[14]张勇,舒威虎,王继猛,等.含苯并咪唑基配体的锌配合物的晶体结构和催化对硝基苯磷酸酯水解的活性研究[J].无机化学学报,2013,29(2):419-423.
[15]Shi Q,Chen L L,Liu D F,et al.A new tetranuclear nickel complex based on the benzimidazole ligand for the controllable polymerization of methyl methacrylate[J].Inorg Chem Commun,2013,29:22-26.
[16]王璐,段冉冉,赵盼,等.含2-氨甲基苯并咪唑铜(Ⅱ)配合物的合成、表征、抑菌活性及与DNA作用的研究[J].华南农业大学学报,2014,35(2):90-95.
[17]刘希慧,卓馨.二(2’-吡啶基)苯并咪唑水合锌配合物的合成和结构表征[J].人工晶体学报,2014,43(1):248-261.
[18]赵越,翟玲玲,孙为银.含苯并咪唑基配体Zn(Ⅱ)、Cd(Ⅱ)配位聚合物的合成、结构以及荧光性质研究[J].无机化学学报,2014,30(1):99-105.
[19]Nail M S,Svetlana V E,Rosario S,et al.Tridentate Benzimidazole-Pyridine-Tetrazolates as Sensitizers of Europium Luminescence[J].Inorg Chem,2014,53(10):171-5178.
[20]Wang X X,Yu M,Li T,et al.A 3D chiral Zn(II)complex based on achiral ligands 2-(1H-imidazolyl-1-methyl)-1H-benzimidazole and adipate[J].Inorg Chem Commun,2014,40:187-189.
[21]Hennigar T L,Macquarrie D C.Supramolecular Isomerism in Coordination Polymers:Conformational Freedom of Ligands in[Co(NO3)2(1,2–bis(4–pyridyl)ethane)1.5]n[J].Angew Chem Int Ed,1997,36:972–973.
[22]Matthews C J,Clegg W,Heath S L,et al.Coordination of Zn(II),Cd(II),Hg(II),and Ag(I)by Bis(benzimidazole)Ligands[J].Inorg Chem,1998,37:199-207.
[23]Yang J,Ma J F,Liu Y Y,et al.Zheng.Four Novel 3D Copper(II)Coordination Polymers with Different Topologies[J].Eur J Inorg Chem,2005:2174-2180.
[24]Tian A X,Ying J,Peng J,et al.Assembly of the Highest Connectivity Wells-Dawson Polyoxometalate Coordination Polymer:The Use of Organic Ligand Flexibility[J].Inorg Chem,2008,47:3274-3283.
[25]Zhou X H,Du X D,Li G N,et al.Coordination Polymers Assembled from 3,5–Pyrazoledicarboxylic Acid and Bis(triazolyl)Ligands:Chiral and Meso–Structures Induced by Ligand Flexibility and a Six–Connected Self–Catenated Network[J].Cryst Growth Des,2009,9:4487-4496.
[26]Huang S L,Hou H W,Mi L W,et al.Enforced 2D supramolecular structures within hydrogen-bonded molecular cocrystals[J].Journal of Coord Chem,2009,62(12):1964-1971.
[27]Tian L,Niu Z,Yang N,et al.Crystal structures and luminescent properties of zinc(II)and cadmium(II)compounds constructed from 5-sulfoisophthalic acid and flexible bis-triazole ligands[J].Inorg Chim Acta,2011,370(1):230-235.
[28]Zhai Q G,Gao X,Li S N,et al.Solvothermal synthesis,crystal structures and photoluminescence properties of the novel Cd/X/α,ω-bis(benzotriazole)alkane hybrid family(X=Cl,Br and I)[J].Cryst Eng Comm,2011,13:1602-1616.
[29]Cao D P,Qin L,Yao X Q,et al.Synthesis,characterization and crystal structure of one Cu(II)complex with flexible tetrapyridine and fatty acid ligand[J].Inorg Chem Commun,2013,29:27-29.
[30]Yang Y T,Cheng F X,Tu C Z,et al.A novel(3,4)-connected Cd(II)-coordination polymer with 3-fold interpenetration assembled from 5-Nitrobenzene-1,2,3-tricarboxylate and flexible 1,6-bis(imidazol-1-yl)-hexane ligands[J].Inorg Chem Commun,2013,29:106-109.
[31]姜娈.双苯并咪唑类配体的合成与应用研究[J].合成材料老化与应用,2011,40(4):41-45.
[32]Shriner R L,Upson R W.Bis-benzimidazoles form dibasic acids[J].J Am Chem Soc,1941,63(8):2277-2278.
[33]Roderick W R,Nordeen C W.Bisbenzimidazoles potent inhibitors of rhinoviruses[J].J Med Chem,1972,15(6):655-658.
[34]胡光耀.双(2-苯并咪唑基)烷烃的合成及结构表征[J].生命科学与医药卫生,2011(2):67-69.
[35]易绣光,聂旭亮,温辉梁.双(2-苯并咪唑基)辛烷的合成及其晶体结构[J].井冈山大学学报:自然科学版,2011,32(2):44-45.
[36]Lane E S.A modified benzimidazole synthesis[J].J Chem Soc,1953,4:2238-2240.
[37]Vyas P C,Oza C K,Goyal A K.A simple synthesis of 2,2’-bis-benzimidazole[J].Chem I nd(London),1980,7:287-288.
[38]宋林清,谭祖干,徐贤伦.微波辐射下双(2-苯并咪唑基)烷烃的合成[J].合成化学,2001,9(2):175-176.
[39]王璐瑶,韩洁,李晓娟,等.双(2-苯并咪唑基)烷烃的简便合成方法[J].化学试剂,2005,27(5):317-320.
[40]吕维忠,刘波,韦少慧,等.微波辐射下双(2-苯并咪唑基)丙烷的合成与结构表征[J].化学研究与应用,2007,19(7):817-819.
[41]戴卫东,李泉,钱礼华.双(2-苯并咪唑基)乙烷的合成工艺研究[J].江西师范大学学报:自然科学版,2009,33(3):275-278.
[42]Hein D W,Alheim R J,Leavitt J J.The Use of Polyphosphoric Acid in the Synthesis of 2-Aryl-and2-Alkyl-substituted Benzimidazoles,Benzoxazoles and Benzothiazoles[J].J Am Chem Soc,1957,79(2):427-429.
[43]Lin S Y,Isome Y,Stewart E,et al.Microware-assisted one step high-throughput synthesis is of benzimidazoles[J].Tetrahedron Letters,2006,47:2883-2886.
[44]Gedyer R,Smith F,Westaway K.The use of microwave ovens for rapid organic synthesis[J].Tetrahedron Lett,1986,27(3):279-282.
[45]Geratz J D,Tidwell R R,Lowbardy R J,et al.Streptococal cell wall-induced systemic disease:Beneficial effects of transbis(5-amidino-2-benzidazolyl)ethene,a novel,macrophage-directed anti-inflammatory agent[J].Am J Pathol,1991,139(4):921-931.
[46]Guo Dong Feng,Luan Jiang,Qiang Chen,et al.A2D Wavy Parquet Architecture Based on the Biphenyl-3,3’,4,4’-tetracarboxylic Acid and Bis(2-benzimidazole)alkanes Ligands[J].Chinese J.Struct.Chem.(Jiegou Huaxue),2013,32(1):45-50.
[47]Zhou Q,Yang P.Crystal structure and DNA-binding studies of a new Cu(II)complex involving benzimidazole[J].Inorg Chim Acta,2006,359:1200-1206.
[48]Zimmer C,Wahnert U.Nonintercalating DNA-binding ligands:Specificity of the interaction and their use as tools in biophysical,biochemical and biological investigation of the genetic material[J].Prog Biophys Mol Biol,1986,47:31-112.
[49]高娟丽.双苯并咪唑类衍生物的合成及其抑菌活性研究[D].咸阳:西北农林科技大学,2012.
[50]段彩明,韩萍扬.N,N’-二(对甲苯磺酞)亚磺酰胺-S-(2-苯并咪唑基)钠在照相乳剂中的超增感应用[J].感光材料,1996(6):19-22.
[51]沈永嘉.苯并咪唑酮颜料及其应用[J].化工科技市场,2001(4):6-11.
[52]赵建喜,王艾戎.咪唑衍生物及其应用[J].绝缘材料,2002(5):36-39.
[53]卢艳华,庞正智,王磊.新型环氧树脂固化剂2-烷基苯并咪唑的研究[J].热固性树脂,2003,18(6):1-3.
[54]浦鸿汀,刘改花.磷酸掺杂新型聚苯并咪唑的质子导电性能的研究[J].功能材料,2005,36(2):217-202.