氮杂杯[4]芳烃衍生物的合成及其与RDX、HMX的配合研究
摘要
论文合成了氮杂杯[4]芳烃及其衍生物，并对其与黑索今、奥克托今的配合性能进行了研究。
三聚氯氰和对苯二胺为原料，碳酸钾为缚酸剂，四氢呋喃为溶剂，冰浴条件下合成N，N′-二（4,6-二氯-1,3,5－均三嗪-2-基）-1,4－苯二胺(comp.1)，产率90.0%，mp：319℃；comp.1和对苯二胺（摩尔为1:1）为原料，丙酮为溶剂，室温下反应，合成四氮杂杯[2]p-二氨基芳烃[2]三嗪(comp.3)，产率为45.5%，mp>300℃。产物结构经IR和1HNMR表征。
三聚氯氰和间苯二胺为原料，碳酸钾为缚酸剂，四氢呋喃为溶剂，冰浴条件下合成N，N′-二（4,6-二氯-1,3,5－均三嗪-2-基）-1,3－苯二胺(comp.2)，产率85.8%，mp：220℃；comp.2和间苯二胺（摩尔为1:1）为原料，丙酮为溶剂，室温下反应，合成四氮杂杯[2]m-二氨基芳烃[2]三嗪(comp.4)，产率30.0%，mp>300℃。产物结构经IR和1HNMR表征。
comp.3、omp.4分别和叠氮钠（摩尔比为1:3）在40~50℃下反应，DMF为溶剂，分别生成四氮杂杯[2] p-二氨基芳烃[2]-2-叠氮基-1,3,5-三嗪，四氮杂杯[2] m-二氨基芳烃[2]-2-叠氮基-1,3,5-三嗪(comp.5、comp.6)，产率为90.0%，mp均>300℃；高压反应釜中，将comp.3、comp.4分别溶于DMF，通氨气，80℃下反应，分别生成四氮杂杯[2] p-二氨基芳烃[2]-2-氨基-1,3,5-三嗪，四氮杂杯[2] m-二氨基芳烃[2]-2-氨基-1,3,5-三嗪(comp.7、comp.8)，产物结构经IR和1HNMR表征。
采用荧光光谱法研究了氮杂杯[4]芳烃及其衍生物与黑索今、奥克托今在溶液中的配合性能。结果表明，当comp.5加到黑索今的DMF溶液中时，能够得到稳定的配合物；采用XRD研究了氮杂杯[4]芳烃及其衍生物与黑索今、奥克托今的配合性能，结果表明主客体之间发生了相互作用。
In this paper,we synthesized aza-bridged calix[4]arene and its derivation.Andstudied supramolecular complex with RDX and HMX.
Using cyanuric chloride and p-phenylenediamine as materials,potassium carbonatewas taken as neutralisatal reagents,THF as solvent,synthesized N,N′-di(4,6-di chlorine-1,3,5-s-triazine-2-base)-1,4-dipheylamine(comp.1),the yield may up to 90.0%,mp is319℃;synthesized azacalix[4]arenes (comp.3) by comp.1 and p-phenylenediamine (themole ratio 1:1),in room temperature, acetone as solvent ,the yield is 45.5%,mp>300℃.The product were characterized through IR and 1H NMR.
Using cyanuric chloride and m-phenylenediamine as materials,potassium carbonatewas taken as neutralisatal reagents,THF as solvent,synthesized N,N′-di(4,6-di chlorine-1,3,5-s-triazine-2-base)-1,3dipheylamine (comp.2), the yield is 85.8%,mp is 300℃;synthesized azacalix[4]arenes (comp.4) by comp.2 and m-phenylenediamine (the moleratio 1:1),in room temperature,acetone as solvent,the yield is 30.0%, mp>300℃.Theproduct were characterized through IR and 1H NMR.
Taking comp.3、comp.4 and sodium azide(the mole ratio 1:3) as materials,DMF assolvent.in 40~50℃, synthesized comp.5,comp.6, the yield is 90.0% , mp>300;In highpressure kettle, 80℃,dissolved comp.3,comp.4 to DMF,then connect ammonia t oDMF,get comp.7,comp.8. The product were characterized through IR and 1H NMR.
The complex properties of aza-bridged calix[4]arene and RDX,HMX in solution wereinvestigated by fluorescence spectrum.The experiment results showed that when comp.5is added into the solution of RDX,it can get a steady compound.We also investigated thecomplex by XRD.The experiment results showed that there was reciprocity between hostand guest.
三聚氯氰和对苯二胺为原料，碳酸钾为缚酸剂，四氢呋喃为溶剂，冰浴条件下合成N，N′-二（4,6-二氯-1,3,5－均三嗪-2-基）-1,4－苯二胺(comp.1)，产率90.0%，mp：319℃；comp.1和对苯二胺（摩尔为1:1）为原料，丙酮为溶剂，室温下反应，合成四氮杂杯[2]p-二氨基芳烃[2]三嗪(comp.3)，产率为45.5%，mp>300℃。产物结构经IR和1HNMR表征。
三聚氯氰和间苯二胺为原料，碳酸钾为缚酸剂，四氢呋喃为溶剂，冰浴条件下合成N，N′-二（4,6-二氯-1,3,5－均三嗪-2-基）-1,3－苯二胺(comp.2)，产率85.8%，mp：220℃；comp.2和间苯二胺（摩尔为1:1）为原料，丙酮为溶剂，室温下反应，合成四氮杂杯[2]m-二氨基芳烃[2]三嗪(comp.4)，产率30.0%，mp>300℃。产物结构经IR和1HNMR表征。
comp.3、omp.4分别和叠氮钠（摩尔比为1:3）在40~50℃下反应，DMF为溶剂，分别生成四氮杂杯[2] p-二氨基芳烃[2]-2-叠氮基-1,3,5-三嗪，四氮杂杯[2] m-二氨基芳烃[2]-2-叠氮基-1,3,5-三嗪(comp.5、comp.6)，产率为90.0%，mp均>300℃；高压反应釜中，将comp.3、comp.4分别溶于DMF，通氨气，80℃下反应，分别生成四氮杂杯[2] p-二氨基芳烃[2]-2-氨基-1,3,5-三嗪，四氮杂杯[2] m-二氨基芳烃[2]-2-氨基-1,3,5-三嗪(comp.7、comp.8)，产物结构经IR和1HNMR表征。
采用荧光光谱法研究了氮杂杯[4]芳烃及其衍生物与黑索今、奥克托今在溶液中的配合性能。结果表明，当comp.5加到黑索今的DMF溶液中时，能够得到稳定的配合物；采用XRD研究了氮杂杯[4]芳烃及其衍生物与黑索今、奥克托今的配合性能，结果表明主客体之间发生了相互作用。
In this paper,we synthesized aza-bridged calix[4]arene and its derivation.Andstudied supramolecular complex with RDX and HMX.
Using cyanuric chloride and p-phenylenediamine as materials,potassium carbonatewas taken as neutralisatal reagents,THF as solvent,synthesized N,N′-di(4,6-di chlorine-1,3,5-s-triazine-2-base)-1,4-dipheylamine(comp.1),the yield may up to 90.0%,mp is319℃;synthesized azacalix[4]arenes (comp.3) by comp.1 and p-phenylenediamine (themole ratio 1:1),in room temperature, acetone as solvent ,the yield is 45.5%,mp>300℃.The product were characterized through IR and 1H NMR.
Using cyanuric chloride and m-phenylenediamine as materials,potassium carbonatewas taken as neutralisatal reagents,THF as solvent,synthesized N,N′-di(4,6-di chlorine-1,3,5-s-triazine-2-base)-1,3dipheylamine (comp.2), the yield is 85.8%,mp is 300℃;synthesized azacalix[4]arenes (comp.4) by comp.2 and m-phenylenediamine (the moleratio 1:1),in room temperature,acetone as solvent,the yield is 30.0%, mp>300℃.Theproduct were characterized through IR and 1H NMR.
Taking comp.3、comp.4 and sodium azide(the mole ratio 1:3) as materials,DMF assolvent.in 40~50℃, synthesized comp.5,comp.6, the yield is 90.0% , mp>300;In highpressure kettle, 80℃,dissolved comp.3,comp.4 to DMF,then connect ammonia t oDMF,get comp.7,comp.8. The product were characterized through IR and 1H NMR.
The complex properties of aza-bridged calix[4]arene and RDX,HMX in solution wereinvestigated by fluorescence spectrum.The experiment results showed that when comp.5is added into the solution of RDX,it can get a steady compound.We also investigated thecomplex by XRD.The experiment results showed that there was reciprocity between hostand guest.
引文
[1] Steed J W,Atwood J L.超分子化学[M].化学工业出版社, 2006,7:1～4.
[2] 刘育,尤长城,张衡益. 超分子化学—合成受体的分子识别与组装[M].天津：南开大学出版社,2002:306-320.
[3] Backeland L H.Address of acceptance the ch emical constution of resinous phenoliccondensation products[J].Ind.Eng.Chem.1913,5:506.
[4] Balram Dhawan, Shou-I Chen, C David Gutsche. Calixarenes.19. Studies of the formationof calixarenes via condensation of p -alkylphenols and formaldehyde[J]. Makromol. Chem.1987, 188: 921~950.
[5] Gutsche C D, Lorenz J, Bauer. Calixarenes. 13. The Conformational Properties of Calix -
[4]arenes, Calix[6]arenes, Calix[8]arenes, and Oxacalixarenes[J]. J. Am. Chem. Soc,1985,107:6052-6059.
[6] Alekseeva E A, Mazepa A V, Gren A I.. Synthesis and Conformational Characte risticsofBenzyl-Substituted p-tert-Butylcalixarenes[J]. Russian Journal of General Chemistry,2001,11:1786-1792.
[7] Gutsche C D, Lorenz J, Bauer. Calixarenes. 14. The Conformational Properties of theEthers and Esters of the Calix[6]arenes and the Calix[ 8]arenes[J]. J.Am.Chem.Soc,1985,107 ,6059-6063.
[8] 郭勋,刘芳,陆国元.杯芳烃衍生物研究进展[J].有机化学,2005,25（9）,1021-1028.
[9] Gutsche C D.Calixarenes,The Royalsociety of Chemistry[M],Cambridge,England,1989.
[10] Gutsche C D. Solvent extraction of alkaline -earth ions by dicarboxylated calix[4] arenes[J].Aldrichimica Acta ,1995,28,3.
[11] T Sone, Y Ohba, K Moriya, et al. Synthesis and properties of sulfur -bridged analogs ofp-tert-butylcalix[4]arene[J].Tetrahedron,1997,53:10689 -10692.
[12] H Kumagai, M Hasegawa, S Miyanari, e t al. Facile synthesis of p-tert- butylthia calix[4]-arene by the reaction of p- tert-butylphenol with elemental sulfur in the presence of baes[J].Tretrahedron Lett,1997,39 :3971 -3 975.
[13] Iki N,Miyano S,Selective oxidation of thiacalix[4]arenes to th e sulfinyl and sulfonyl-calix[4]arenes and their coordination ability to metal ions[J].J.Chem.Soc.Perkin Trans.1998,2,2745.
[14] Delaigue X, Hossini M W.Multicavitands ⅲ :Synthesis and NMR studies of atri-directional koiland composed of three p -tert butylcalix[4]arenes units fused by twosilicon atoms[J].Chem.Soc.1994:1579 -1580.
[15] H Kumagai, M Hasegawa.Surface orientation and complex formation of new calixarenederivative containing sulfur ligands[J].Tetrahedron lett.1997,38,3971.
[16] Jeffrey L,Katz,Synthesis of Functionalized Oxacalix[4]arenes[J]. Oranic Letter,2005,7(1):91-94.
[17] Komatsu, N T.New synthetic route to homooxacalix[n]arenas via reductive coupling ofdiformylphenols [J].Tetra Lett,2001,42(9):1733-1736.
[18] 刘世岚,李海兵,钟振林.氧杂同杯芳烃的研究进展[J].有机化学,2004,4（24）:386-395.
[19] E E Boros,A O Davis.Isolation and characterization of a new oxacalixarene[J].Org.Chem.1996,61,2553-2555.
[20] J L Katz,M B Feldman,R R Conry.Structure and C -H-pinteractions in DMF inclusioncomplexes of homoazacalix[4]arenes[ J].Org.Lett,2005,7:91-94.
[21] A.Toth,C.Floriani,A.Chiesi -villa,C.Guastini.Dinuclear copper(I )benzoate complexesbinding isocyanides and azocompounds[J].Organic Chemistry,1987,26 :23 6 -241.
[22] Floriant C .Transitionm etal. Complexes as bifunctional carr iers of polar organometallic:their application To large molecule modifications and to hydrocardonactivationc arbon[J].Puer and applied chemistry,1998,28 : 13 76 -1 381.
[23] B .R .Cameron,F .C .J. Van Veggel,D .N .R einhoudt.Transitionm etalcomplexes Oflower rim 1,3-diphos phinite and 1 ,3- diphosphino calix[4]arenas[J].J. Org. Chem.,1995,60 :2802-2805.
[24] Hajek F, Graf E., Hosseini M. W., et al. Synthesis and X -ray analysis of unsymmetricallinear koiland baesd on double fusion of two difeernt calix[ 4]arene by two silicon atoms[J].Tetra Lett, 1997,38 :4555-4559.
[25] Giannini L, Solari E. Ethylene rearrangements to MC, M=C, and M C functiona litiesover a tungsten- Oxo surface illustrated by the W (Ⅳ )calix[4]aerne fragment[J].J. Am.Chem.Soc.,1998,35:2825 .
[26] P D Beer,P A Gale.Anion precognition and sensing:the state of the art and futureperspectives[J].Angew Chem .Int .E D.Eng.l,2001,40 (3):486 -516.
[27] P D Beer,M G Drew .Synthesis and anion coordination chemistry of new calix[4]arenePyridinium receptors[J].J. Chem.Soc.Perkin.Trans.2, 2000,3(5):11 -51.
[28] P Thuery,M Nierlich.Synthesis and cation complexation studies of a new tetra (2-pyridyl-methyl)amide calix[4]arene[J].Chem,2001:637 -643.
[29] H Takemura,Y Kozima,T Inazu.Synthesis and disprop ortionation of ABAC-typeoxavalixarenes[J].Tetrahed.Lett,1999,40:6431 -6434.
[30] M X Wang,X H Zheng,Q Y Zheng.Flourene -containing sulfonated poly(arylene ether1,3,4-oxadiazole) as proton-exchange membrane for PEM fuel cell application[J].Chem.Int.Ed, 2004,43:838.
[31] M X Wang,H B Yang.A geral and high yielding fragment coupling synthesis ofheteroatom-bridged calixarenes and the unprecedented examples of calixarenes cavityfine-tuned by bridg[J].Jam.Chem.Soc,2004,126:15412 -15422.
[32] Gale P A,Kral V.Synthesis,Steucture,and [60]Fullerene complexation properties ofazacalix[m]arene[n] pyridines[J].Chem.Commun,1998:1 -8.
[33] Turner B,Eichen Y,Angew.Synthesis of heteroatom -bridged calixarenes[J]. Chem. IntEd,1998,37:2475-2479 .
[34] Sessler J L,Gale P A.Synthesis and properties of Me2Ge-bridged arenes[J].Pure&ApplChem,1998,70:2401-2408.
[35] Miyaji H,Jr P A,Sessler J L.Heteroatom -bridged calixarenes[J].Chem Commun,1999:1723-1724.
[36] Anellip L, Lunazzi L,Montanari F,et al.Dou -bly and triply bridged polyoxa-poly-azaheterophanes de-rived from 2,4,6-trichloro-s-triazine [J].J Org Chem, 1984, 49:4197-4203.
[37] Lowikd W P,Lowe C R.Synthesis of macrocylic,tria -zine-based recrptor molecules[J].Eur J Org Chem,2001,23:2825-2839.
[38] Graubaum H,Lutze G,Titfelba ch F,et al.New ayacyclophanes form cyanuric chloride anddiamines[J]. J Prakt Chem/Chem-ztg,1995,337(5):401-404.
[39] 戈蔓,花成文,苟小锋,等.四氮杂杯[2]芳烃[4]三嗪的合成和表征[J], 西北大学学报:自然科学版,2007,37(2):228-230.
[40] 詹威强,胡幼元.三聚氯氰衍生物在精细化工中的应用现状及发展趋势[J].化学工业与工程技术,2001, 2（22）:5-9.
[41] 赵美法.三聚氯氰及其下游产品的开发与应用[J].化工中间体, 2002 ,17:16-22.
[42] 戈蔓.四氮杂杯芳烃和四氮杂环蕃的合成研究[D].西北大学硕士学位论文,2005.
[43] 华北工学院工业炸药培训教材编审委员会.工业炸药工艺学[M].华北工学院出版社:79-80.
[44] 任特生.硝胺及硝酸醋炸药化学与工艺学[M].北京:兵器工业出版社, 1994,27-165.
[45] 任福德.Gaussian-98/03 计算的操作及应用（内部资料）.2006:6-15.
[46] 王进. 叠氮硝酸酯对硝胺改性双基推进剂燃烧性能的影响[J]. 火炸药学报,200l,24(2):22-24.
[47] 许金钩,王尊本.荧光分析法[M].科学出版社,2006.
[48] 方国勇,徐丽娜.对于3-硝基-1,2,4-三唑-5-酮与NH3 及H2O 分子间相互作用的理论研究[J]. 化学学报.2005 1055-1061.
[49] Sándor Kunsági-Máté, István Bitter, Alajos Grün. Cavity shaped host -guest interaction ofdistally dialkylatedcalix[4]arenes with 1 -chloro-4-(trifluoromethyl) benzene[J].Analytica Chimica Acta, 2001, 443: 227 -234.
[2] 刘育,尤长城,张衡益. 超分子化学—合成受体的分子识别与组装[M].天津：南开大学出版社,2002:306-320.
[3] Backeland L H.Address of acceptance the ch emical constution of resinous phenoliccondensation products[J].Ind.Eng.Chem.1913,5:506.
[4] Balram Dhawan, Shou-I Chen, C David Gutsche. Calixarenes.19. Studies of the formationof calixarenes via condensation of p -alkylphenols and formaldehyde[J]. Makromol. Chem.1987, 188: 921~950.
[5] Gutsche C D, Lorenz J, Bauer. Calixarenes. 13. The Conformational Properties of Calix -
[4]arenes, Calix[6]arenes, Calix[8]arenes, and Oxacalixarenes[J]. J. Am. Chem. Soc,1985,107:6052-6059.
[6] Alekseeva E A, Mazepa A V, Gren A I.. Synthesis and Conformational Characte risticsofBenzyl-Substituted p-tert-Butylcalixarenes[J]. Russian Journal of General Chemistry,2001,11:1786-1792.
[7] Gutsche C D, Lorenz J, Bauer. Calixarenes. 14. The Conformational Properties of theEthers and Esters of the Calix[6]arenes and the Calix[ 8]arenes[J]. J.Am.Chem.Soc,1985,107 ,6059-6063.
[8] 郭勋,刘芳,陆国元.杯芳烃衍生物研究进展[J].有机化学,2005,25（9）,1021-1028.
[9] Gutsche C D.Calixarenes,The Royalsociety of Chemistry[M],Cambridge,England,1989.
[10] Gutsche C D. Solvent extraction of alkaline -earth ions by dicarboxylated calix[4] arenes[J].Aldrichimica Acta ,1995,28,3.
[11] T Sone, Y Ohba, K Moriya, et al. Synthesis and properties of sulfur -bridged analogs ofp-tert-butylcalix[4]arene[J].Tetrahedron,1997,53:10689 -10692.
[12] H Kumagai, M Hasegawa, S Miyanari, e t al. Facile synthesis of p-tert- butylthia calix[4]-arene by the reaction of p- tert-butylphenol with elemental sulfur in the presence of baes[J].Tretrahedron Lett,1997,39 :3971 -3 975.
[13] Iki N,Miyano S,Selective oxidation of thiacalix[4]arenes to th e sulfinyl and sulfonyl-calix[4]arenes and their coordination ability to metal ions[J].J.Chem.Soc.Perkin Trans.1998,2,2745.
[14] Delaigue X, Hossini M W.Multicavitands ⅲ :Synthesis and NMR studies of atri-directional koiland composed of three p -tert butylcalix[4]arenes units fused by twosilicon atoms[J].Chem.Soc.1994:1579 -1580.
[15] H Kumagai, M Hasegawa.Surface orientation and complex formation of new calixarenederivative containing sulfur ligands[J].Tetrahedron lett.1997,38,3971.
[16] Jeffrey L,Katz,Synthesis of Functionalized Oxacalix[4]arenes[J]. Oranic Letter,2005,7(1):91-94.
[17] Komatsu, N T.New synthetic route to homooxacalix[n]arenas via reductive coupling ofdiformylphenols [J].Tetra Lett,2001,42(9):1733-1736.
[18] 刘世岚,李海兵,钟振林.氧杂同杯芳烃的研究进展[J].有机化学,2004,4（24）:386-395.
[19] E E Boros,A O Davis.Isolation and characterization of a new oxacalixarene[J].Org.Chem.1996,61,2553-2555.
[20] J L Katz,M B Feldman,R R Conry.Structure and C -H-pinteractions in DMF inclusioncomplexes of homoazacalix[4]arenes[ J].Org.Lett,2005,7:91-94.
[21] A.Toth,C.Floriani,A.Chiesi -villa,C.Guastini.Dinuclear copper(I )benzoate complexesbinding isocyanides and azocompounds[J].Organic Chemistry,1987,26 :23 6 -241.
[22] Floriant C .Transitionm etal. Complexes as bifunctional carr iers of polar organometallic:their application To large molecule modifications and to hydrocardonactivationc arbon[J].Puer and applied chemistry,1998,28 : 13 76 -1 381.
[23] B .R .Cameron,F .C .J. Van Veggel,D .N .R einhoudt.Transitionm etalcomplexes Oflower rim 1,3-diphos phinite and 1 ,3- diphosphino calix[4]arenas[J].J. Org. Chem.,1995,60 :2802-2805.
[24] Hajek F, Graf E., Hosseini M. W., et al. Synthesis and X -ray analysis of unsymmetricallinear koiland baesd on double fusion of two difeernt calix[ 4]arene by two silicon atoms[J].Tetra Lett, 1997,38 :4555-4559.
[25] Giannini L, Solari E. Ethylene rearrangements to MC, M=C, and M C functiona litiesover a tungsten- Oxo surface illustrated by the W (Ⅳ )calix[4]aerne fragment[J].J. Am.Chem.Soc.,1998,35:2825 .
[26] P D Beer,P A Gale.Anion precognition and sensing:the state of the art and futureperspectives[J].Angew Chem .Int .E D.Eng.l,2001,40 (3):486 -516.
[27] P D Beer,M G Drew .Synthesis and anion coordination chemistry of new calix[4]arenePyridinium receptors[J].J. Chem.Soc.Perkin.Trans.2, 2000,3(5):11 -51.
[28] P Thuery,M Nierlich.Synthesis and cation complexation studies of a new tetra (2-pyridyl-methyl)amide calix[4]arene[J].Chem,2001:637 -643.
[29] H Takemura,Y Kozima,T Inazu.Synthesis and disprop ortionation of ABAC-typeoxavalixarenes[J].Tetrahed.Lett,1999,40:6431 -6434.
[30] M X Wang,X H Zheng,Q Y Zheng.Flourene -containing sulfonated poly(arylene ether1,3,4-oxadiazole) as proton-exchange membrane for PEM fuel cell application[J].Chem.Int.Ed, 2004,43:838.
[31] M X Wang,H B Yang.A geral and high yielding fragment coupling synthesis ofheteroatom-bridged calixarenes and the unprecedented examples of calixarenes cavityfine-tuned by bridg[J].Jam.Chem.Soc,2004,126:15412 -15422.
[32] Gale P A,Kral V.Synthesis,Steucture,and [60]Fullerene complexation properties ofazacalix[m]arene[n] pyridines[J].Chem.Commun,1998:1 -8.
[33] Turner B,Eichen Y,Angew.Synthesis of heteroatom -bridged calixarenes[J]. Chem. IntEd,1998,37:2475-2479 .
[34] Sessler J L,Gale P A.Synthesis and properties of Me2Ge-bridged arenes[J].Pure&ApplChem,1998,70:2401-2408.
[35] Miyaji H,Jr P A,Sessler J L.Heteroatom -bridged calixarenes[J].Chem Commun,1999:1723-1724.
[36] Anellip L, Lunazzi L,Montanari F,et al.Dou -bly and triply bridged polyoxa-poly-azaheterophanes de-rived from 2,4,6-trichloro-s-triazine [J].J Org Chem, 1984, 49:4197-4203.
[37] Lowikd W P,Lowe C R.Synthesis of macrocylic,tria -zine-based recrptor molecules[J].Eur J Org Chem,2001,23:2825-2839.
[38] Graubaum H,Lutze G,Titfelba ch F,et al.New ayacyclophanes form cyanuric chloride anddiamines[J]. J Prakt Chem/Chem-ztg,1995,337(5):401-404.
[39] 戈蔓,花成文,苟小锋,等.四氮杂杯[2]芳烃[4]三嗪的合成和表征[J], 西北大学学报:自然科学版,2007,37(2):228-230.
[40] 詹威强,胡幼元.三聚氯氰衍生物在精细化工中的应用现状及发展趋势[J].化学工业与工程技术,2001, 2（22）:5-9.
[41] 赵美法.三聚氯氰及其下游产品的开发与应用[J].化工中间体, 2002 ,17:16-22.
[42] 戈蔓.四氮杂杯芳烃和四氮杂环蕃的合成研究[D].西北大学硕士学位论文,2005.
[43] 华北工学院工业炸药培训教材编审委员会.工业炸药工艺学[M].华北工学院出版社:79-80.
[44] 任特生.硝胺及硝酸醋炸药化学与工艺学[M].北京:兵器工业出版社, 1994,27-165.
[45] 任福德.Gaussian-98/03 计算的操作及应用（内部资料）.2006:6-15.
[46] 王进. 叠氮硝酸酯对硝胺改性双基推进剂燃烧性能的影响[J]. 火炸药学报,200l,24(2):22-24.
[47] 许金钩,王尊本.荧光分析法[M].科学出版社,2006.
[48] 方国勇,徐丽娜.对于3-硝基-1,2,4-三唑-5-酮与NH3 及H2O 分子间相互作用的理论研究[J]. 化学学报.2005 1055-1061.
[49] Sándor Kunsági-Máté, István Bitter, Alajos Grün. Cavity shaped host -guest interaction ofdistally dialkylatedcalix[4]arenes with 1 -chloro-4-(trifluoromethyl) benzene[J].Analytica Chimica Acta, 2001, 443: 227 -234.