两类对Fe（Ⅲ）有比率荧光响应的杂环分子的合成及性质研究
|
摘要
如今,随着经济的发展和社会的进步,越来越多的人意识到环境对经济、社会发展和人民生活质量提高的重要性,而工业化的发展尤其是重工业的发展对水体、大气以及生物体带来不同程度的影响,各种污染严重威胁着人们的生活。因此,方便快速的检测对水体、大气及生物体的有害物质成为各领域学者们研究的焦点。随着人们对于荧光化合物认识的逐渐深入,人们发现探针的分子结构和环境对其光谱行为以及发光强度都会带来规律性的影响,故而人们在设计荧光传感器分子时,常常通过化学手段对探针进行分子结构上的修饰,以期获得新的探针达到更为优良的检测效果。
本文设计合成的2-(10-氯代蒽基-)-5-(2-吡啶基)-1,3,4-噻二唑在紫外下显示明亮的黄绿色荧光,同时测试显示其在微摩浓度下对Fe3+有比率荧光选择性,并表现出很高的专一性,质谱测试也反映出荧光分子与Fe3+是1：1的配位模式；而本文设计并合成得到的另一类分子：4-(9-蒽基)-2-(2-吡啶基)噻唑在紫外下显示出明亮的蓝紫色荧光,荧光测试也显示其对Cu2+、Hg2+和Fe3+具有很好的比率荧光选择性。其中Cu2+、Hg2+猝灭的是蒽部分的荧光发射,而与之正好相反的是Fe3+却猝灭的是吡啶-噻唑部分的荧光发射；同时在水中时,噻唑的荧光较甲醇中增强了近1000倍,而进一步加入各种金属离子时体系荧光又有不同程度的猝灭,故本部分以H20和各种金属离子(Mn+)为两个输入信号,以噻唑的特征荧光发射作为输出信号,构建了一个典型的双输入INH(抑制型)荧光分子逻辑门。
Nowadays,with the development of economy and the progress of society, more and more people realize the importance of environment to the development of economy and the quality of people's life.The development of industry, especially heavy industry brought impact on waters,atmosphere and organisms and people's life are threatened seriously. So a rapid and convenient method for the detection of hazardous materials in the waters,atmosphere and organs becomes the focus of scientists of all fields.As people gradually for the fluorescent compounds-depth understanding,it was discovered the molecular structure and probe environment and the luminous intensity of their spectral behavior will bring the law in effect,when people design the fluorescent sensor molecules,they often modify the molecular structure of probe in order to obtain new probes to be better detection results.
Using the simple approach, the following two kinds of new compounds were prepared:2-(10-chloroanthracen-9-yl)-5-(pyridin-2-yl)-1,3,4-thiadiazole and 4-(anthracen-9-yl)-2-(pyridin-2-yl)thiazole.The former probe,emitting yellow-green fluorescence under the ultraviolet light,showed a high ratiometric fluorescent selectivity to iron(Ⅲ) without interferences of the background metal ions.The latter molecule was synthesized and characterized and the absorption spectra and the effects of metal ions on the fluorescent intensity were studied.The experimental results showed that fluorescence intensity decreased upon addition of twelve kinds of metal ions to different extent in methanol solutions,while the quenched behaviors of Cu2+, Hg2+and Fe3+were exceptional.In neutral aqueous solutions,the fluorescent intensity of system enhanced approximately 1000-fold than previous conditions. On the basis of these studies, an INH fluorescent molecular logic gate was fabricated with H2O and metal ions (Mn+) inputs and with emission of APT as the output signal.
本文设计合成的2-(10-氯代蒽基-)-5-(2-吡啶基)-1,3,4-噻二唑在紫外下显示明亮的黄绿色荧光,同时测试显示其在微摩浓度下对Fe3+有比率荧光选择性,并表现出很高的专一性,质谱测试也反映出荧光分子与Fe3+是1：1的配位模式；而本文设计并合成得到的另一类分子：4-(9-蒽基)-2-(2-吡啶基)噻唑在紫外下显示出明亮的蓝紫色荧光,荧光测试也显示其对Cu2+、Hg2+和Fe3+具有很好的比率荧光选择性。其中Cu2+、Hg2+猝灭的是蒽部分的荧光发射,而与之正好相反的是Fe3+却猝灭的是吡啶-噻唑部分的荧光发射；同时在水中时,噻唑的荧光较甲醇中增强了近1000倍,而进一步加入各种金属离子时体系荧光又有不同程度的猝灭,故本部分以H20和各种金属离子(Mn+)为两个输入信号,以噻唑的特征荧光发射作为输出信号,构建了一个典型的双输入INH(抑制型)荧光分子逻辑门。
Nowadays,with the development of economy and the progress of society, more and more people realize the importance of environment to the development of economy and the quality of people's life.The development of industry, especially heavy industry brought impact on waters,atmosphere and organisms and people's life are threatened seriously. So a rapid and convenient method for the detection of hazardous materials in the waters,atmosphere and organs becomes the focus of scientists of all fields.As people gradually for the fluorescent compounds-depth understanding,it was discovered the molecular structure and probe environment and the luminous intensity of their spectral behavior will bring the law in effect,when people design the fluorescent sensor molecules,they often modify the molecular structure of probe in order to obtain new probes to be better detection results.
Using the simple approach, the following two kinds of new compounds were prepared:2-(10-chloroanthracen-9-yl)-5-(pyridin-2-yl)-1,3,4-thiadiazole and 4-(anthracen-9-yl)-2-(pyridin-2-yl)thiazole.The former probe,emitting yellow-green fluorescence under the ultraviolet light,showed a high ratiometric fluorescent selectivity to iron(Ⅲ) without interferences of the background metal ions.The latter molecule was synthesized and characterized and the absorption spectra and the effects of metal ions on the fluorescent intensity were studied.The experimental results showed that fluorescence intensity decreased upon addition of twelve kinds of metal ions to different extent in methanol solutions,while the quenched behaviors of Cu2+, Hg2+and Fe3+were exceptional.In neutral aqueous solutions,the fluorescent intensity of system enhanced approximately 1000-fold than previous conditions. On the basis of these studies, an INH fluorescent molecular logic gate was fabricated with H2O and metal ions (Mn+) inputs and with emission of APT as the output signal.
引文
[1].P. Aisen, M. Wessling-Resnick, E. A. Leibold, Iron metabolism. Curr. Opin. Chem. Biol,1999,3,200-206.
[2].Meneghini, R. Iron homeostasis, oxidative stress, and DNA damage. Free Radical Biol. Med.,1997,23,783-792.
[3].Karlberg T, Lecerof D, Gora M, Silvegren G, Labbe-Bois R, Hansson M, Al-Karadaghi S. Metal Binding to Saccharomyces cerevisiae Ferrochelatase. Biochemistry.2002,41,13499-13506.
[4].Lynch SR. Interaction of Iron with Other Nutrients. Nutr Rev.,1997 Apr; 55(4): 102-110.
[5].J. R. Burdo and J. R. Connor, Brain iron uptake and homeostatic mechanisms:An overview. Biometals,2003,16,63-75.
[6].Yu Xiang,Aijun Tong, A New Rhodamine-Based Chemosensor Exhibiting Selective FeⅢ-Amplified Fluorescence.Org.Lett,2006,8,1549-1552.
[7]Jie Mao,Weisheng Liu, Tuning the Selectivity of Two Chemosensors to Fe(III) and Cr(III).Org.Lett.,2007 Vol 94567-4570
[8].Hee Jung Jung, Yonsei University, Highly Fe3+selective ratiometric fluorescent probe based on imine-linked benzimidazole. Tetrahedron Letters,49(2008) 2960-2964.
[9].Weiying Lin, A Fluorescence-Enhanced Chemodosimeter for Fe3+Based on Hydrolysis of Bis(coumarinyl) Schiff Base. Eur. J. Org. Chem.,2008,2689-2692.
[10].Weiying Lin, A novel ratiometric fluorescent Fe3+sensor based on a phenanthroimidazole chromophore. Analytica Chimica Acta,2009 Vol 634262-266.
[11].A.P.de Silva, H.Q.N.Gunaratne, T.Gunnlaugsson,A.J.M.Huxley. Signaling Recognition Events with Fluorescent Sensors and Switches. Chem.Rev.,1997, 97:1515-1566.
[12]Luigi Fabbrizzi,Antonio Poggo. Sensors and switches from supramolecular chemistry. Chemical Society Reviews,1995,24,197-202.
[13]Maria Espinosa Bosch, Antonio Jesus Ruiz Sanchez, Fuensanta Sanche zhez Rojas, et al., Recent Development in Optical Fiber Biosensors[J]. Sensors, 2007,7:797-859.
[14]Gunnlaugsson T, MacDonail D A, Parker D. Luminescent molecular logic gates: the two-input inhibit (INH) function.J. Chem. Soc, Chem. Commun.,2000,93-94.
[15]de Silva A P, Dixon IM, Gunaratne H Q N, et al.Integration of Logic Functions and Sequential Operation of Gates at the Molecular-Scale. J. Am. Chem. Soc, 1999,121:1393-1394.
[16]Roque A, Pina F, Alves S, et al.Micelle effect on the'write-lock-read-unlock-erase'cycle of 4'-hydroxyflavylium ion. J. Mater. Chem.,1999,9:2265-2270.
[17]Credi A, Balzani V, Langford S J, et al.Logic Operations at the Molecular Level. An XOR Gate Based on a Molecular Machine.J. Am. Chem, Soc,1997,119: 2679-2680.
[18]Pina F, Melo M J, Maestri M, et al. Artificial Chemical Systems Capable of Mimicking Some Elementary Properties of Neurons.J. Am. Chem. Soc,2000, 122:4496-4498.
[19]de Silva A P,Gunaratne H Q N, McCoy C P.A molecular photoionic AND gate based on fluorescent signalling. Nature,1993,364:42-44.
[20]Magri D C, Callan J F, de Silva A P,et al.The Anthracen-9-ylmethyloxy Unit: An Underperforming Motif Within the Fluorescent PET (Photoinduced Electron Transfer) Sensing Framework. Journal of Fluorescence,2005,75:769-775.
[21]Uchiyama S, McClean G D, Iwai K, et al.Membrane Media Create Small Nanospaces for Molecular Computation.J. Am. Chem. Soc,2005,127:8920-8921.
[22]Gust D, Moore T A, Moore A L. Molecular switches controlled by light. Chem. Commun.,2006,1169-1178.
[23]宗国强,吕功煊.基于N-(9-蒽甲基)-L-组氨酸的NOR荧光逻辑门.物理化学学报，2008,24：1902-1906.
[24]H Takakusa, K Kikuchi,Y Urano, S Sakamoto, et al., Design and Synthesis of an Enzyme-Cleavable Sensor Molecule for Phosphodiesterase Activity Based on Fluorescence Resonance Energy Transfer. J. Am.Chem. Soc;2002,124(8); 1653-1657.
[25]H Takakusa, K Kikuchi, Y Urano, H Kojima, T Nagano. A Novel Design Method of Ratiometric Fluorescent Probes Based on Fluorescence Resonance Energy Transfer Switching by Spectral Overlap Integral. Chem.Eur.J.,2003,9, No.71479-1485.
[26]Adachi C, Tsutsui T., Saito S., Blue light-emitting organic electroluminescent devices. Appl. Phys.Lett,1990,56,799.
[27]Bettenhausen J.Strohriegl P., Efficient synthesis of starburst oxadiazole compounds. Adv.Mater.,1996,8,507.
[28]Kido J., Nagai K., Okamoto Y., Skotheim T., Electroluminescence from Polysilane Film Doped with Europium Complex. Chem. Lett,1991,1267.
[29]卢勇,陈静对2-吡啶甲酰肼的合成研究.化学工程与装备，2006年第三期.
[30]Xin J. F.; Ma, J. Z. H.; Hang, S. F., Review of the Methods of Preparing Acyl Chlorides. HEBEI CHEMICAL ENGINEERING AND INDUSTRY,200629(11).
[31]Bentiss, F.; Lagrenee, M., RAPID SYNTHESIS OF 2,5-DISUBSTITUTED 1,3,4-OXADIAZOLES UNDER MICROWAVE IRRADIATION. Synth. Commun.,2001,31,935-938.
[32]李希晨,杨新玲,开振鹏,凌云,N-叔丁基苯基呋喃甲酰肼的合成研究,化学通报，2006年9期.
[33]余书强,芳酰基偶氮化合物和芳基酰肼的合成研究.[硕士学位论文].河南师范大学2004.
[34]J. M. Hoover, A. DiPasquale, J. M. Mayer, Platinum-Catalyzed Intramolecular Hydrohydrazination:Evidence for Alkene Insertion into a Pt-N Bond./. Am. Chem. Soc,2010,132 (14),5043-5053.
[35]Era M., Tsutsui T., Saito S., Organic-inorganic heterostructure electroluminescent device using a layered perovskite semiconductor (C6H5C2H4NH3)2Pbl4. Appl. Phys.Lett.,1994,65,676.
[36]Kido J.,Hayase H.,Hongawa K.,Nagai K.,Okuyama K.,Bright red light-emitting organic electroluminescent devices having a europium complex as an emitter. Appl. Phys. Lett,1994,65,2124.
[37]邱早早,含葡萄糖及苯并氮杂卓骨架的1,2,4-三唑、1,3,4-噁二唑、1,3,4-噻二唑杂环衍生物的合成及抗菌活性.[硕士学位论文].兰州大学2005.
[38]Mazzone G.,Puglisi G.,A new synthesis of symmetrical 2,5-diaryl-1,3,4-thiadiazoles.J.Heterocyclic chem.,1983,20,1399.
[39]Pedersen B.S.,Lawesson S.O.Studies on organophosphorus compounds—XXⅦ: Synthesis of thiono-, thiolo-and dithiolactones. Tetrahedron,1979,35,1339.
[40]Zoltan Kaleta, Brian T. Makowski.,Synthesis and Application of a Fluorous Lawesson's Reagent:Convenient Chromatography-Free Product Purification. Org. Lett, Vol.8, No.6,2006.1093-1095.
[41]Stephen F. M, David R. T., Thiadiazoles and thiadiazolines. Part 3. Synthesis of triazol-3-yl-A2-1,3,4-thiadiazolines and anew synthesis of unsymmetrical 2,5-di-substituted 1,3,4-thiadiazoles. J. CHEM. SOC. PERKIN TRANS I.,1982,1987.
[42]V. Polshettiwar, R. S.Varma.,Greener and rapid access to bio-active heterocycles:one-pot solvent-free synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles.Tetrahedron Letters 49(2008)879-883.
[43]V Balzani, Gomez-Lopez, J. F.Stoddart. Molecular Machines.Ace. Chem. Res.,1998,31:405-414.
[44]V Balzani, A. Credi, F.M.Raytno,Artificial Molecular Machines.Angew. Chem. Int. Ed.,2000,39:3348-3391.
[45]Raymo, F.M.Digital Processing and Communication with Molecular Switches. Adv. Mater.,2002,14:401.
[46]deSilva, A. P.;McClenaghan, N. D.Molecular-Scale Logic Gates.Chem. Eur. J., 2004,10:574.
[47]王文秀.一种选择性检测次氯酸的水溶性荧光分子探针.[硕士学位论文]延边大学化学系,2009.
[48]于海涛,新型有机电致发光材料的合成、结构表征及性质研究.[博士学位论文]南开大学化学系,2002.
[49]W. Lin, L. Long, L. Yuan, Z. Cao, J. Feng, A novel ratiometric fluorescent Fe3+ sensor based on a phenanthroimidazole chromophore. Analytica Chimica Acta., 2009,634,262-266.
[50]P. Healy, B, Skelton, A.white, Structural Studies in the Iron(Ⅲ)/Chloride/α,α Diimine System. Ⅲ*Crystal Structures of Tris(2,2'-bipyridine)iron(Ⅱ)μ-Oxo-bis[trichloroferrate(Ⅲ)] and of'Compound A',μ-Oxo-bis[cis-chlorobis-(1,10-phenanthroline)iron(Ⅲ)] Chloride Solvate. Aust:J. Chem.,1983,36,2057-2064,
[51]M.Collomb, A.Deronzier, K. Gorgy, J.Lepreutre, J.Pecaut, Electrochemical properties of [FeⅢ(L)2Cl2][PF6] and [Fe2Ⅲ,ⅢO(L)4Cl2][PF6]2 [L=2,2'-bipyridine (bpy)and 4,4'-dimethyl-2,2'-bipyridine (dmbpy)].Crystal structures of the dmbpy derivatives. New J. Chem.,1999,785-790.
[52]Zhao, Z. J.; Xing, Y. J.; Wang, Z. X.; Lu, P.Dual-Fluorescent Donor-Acceptor Dyad with Tercarbazole Donor and Switchable Imide Acceptor:Promising Structure for an Integrated Logic Gate. Org. Lett,2007,9:547.
[53]Guo, X. F.;Zhang, D. Q.; Zhang, G. X.;Zhu, D.B.,Monomolecular Logic:"Half-Adder" Based on Multistate/Multifunctional Photochromic Spiropyrans. J. Phys. Chem. B,2004,108:11942.
[54]Qu, D. H.; Ji, F. Y.; Wang, Q. C; Tian, H. A Double INHIBIT Logic Gate Employing Configuration and Fluorescence Changes. Adv. Mater.,2006,18:2035.
[55]Zhao, L.;Sui, D.;Chai, J.;Wang, Y.;Jiang, S.Digital Logic Circuit Based on a Single Molecular System of Salicylidene Schiff Base.J. Phys. Chem. B,2006, 110:24299.
[56]Wang, H. M.; Zhang, D. Q.; Guo, X. F.; Zhu, L. Y.,Tuning the fluorescence of 1-imino nitroxide pyrene with two chemical inputs:mimicking the performance of an "AND"gate. Chem. Commun.,2004:670.
[57]Zhou, X. Y.; Yu, B. R.; Zhang, H. H., Liu, W. S., Both Visual and Fluorescent Sensor for Zn2+Based on Quinoline Platform. Inorg. Chem.,2010,49,4002-4007.
[58]Peng, X. J.; Du, J. J.;Fan, J. L.;A Selective Fluorescent Sensor for Imaging Cd2+ In Living Cells.J. Am. Chem. Soc,2007,129,1500-1501.
[2].Meneghini, R. Iron homeostasis, oxidative stress, and DNA damage. Free Radical Biol. Med.,1997,23,783-792.
[3].Karlberg T, Lecerof D, Gora M, Silvegren G, Labbe-Bois R, Hansson M, Al-Karadaghi S. Metal Binding to Saccharomyces cerevisiae Ferrochelatase. Biochemistry.2002,41,13499-13506.
[4].Lynch SR. Interaction of Iron with Other Nutrients. Nutr Rev.,1997 Apr; 55(4): 102-110.
[5].J. R. Burdo and J. R. Connor, Brain iron uptake and homeostatic mechanisms:An overview. Biometals,2003,16,63-75.
[6].Yu Xiang,Aijun Tong, A New Rhodamine-Based Chemosensor Exhibiting Selective FeⅢ-Amplified Fluorescence.Org.Lett,2006,8,1549-1552.
[7]Jie Mao,Weisheng Liu, Tuning the Selectivity of Two Chemosensors to Fe(III) and Cr(III).Org.Lett.,2007 Vol 94567-4570
[8].Hee Jung Jung, Yonsei University, Highly Fe3+selective ratiometric fluorescent probe based on imine-linked benzimidazole. Tetrahedron Letters,49(2008) 2960-2964.
[9].Weiying Lin, A Fluorescence-Enhanced Chemodosimeter for Fe3+Based on Hydrolysis of Bis(coumarinyl) Schiff Base. Eur. J. Org. Chem.,2008,2689-2692.
[10].Weiying Lin, A novel ratiometric fluorescent Fe3+sensor based on a phenanthroimidazole chromophore. Analytica Chimica Acta,2009 Vol 634262-266.
[11].A.P.de Silva, H.Q.N.Gunaratne, T.Gunnlaugsson,A.J.M.Huxley. Signaling Recognition Events with Fluorescent Sensors and Switches. Chem.Rev.,1997, 97:1515-1566.
[12]Luigi Fabbrizzi,Antonio Poggo. Sensors and switches from supramolecular chemistry. Chemical Society Reviews,1995,24,197-202.
[13]Maria Espinosa Bosch, Antonio Jesus Ruiz Sanchez, Fuensanta Sanche zhez Rojas, et al., Recent Development in Optical Fiber Biosensors[J]. Sensors, 2007,7:797-859.
[14]Gunnlaugsson T, MacDonail D A, Parker D. Luminescent molecular logic gates: the two-input inhibit (INH) function.J. Chem. Soc, Chem. Commun.,2000,93-94.
[15]de Silva A P, Dixon IM, Gunaratne H Q N, et al.Integration of Logic Functions and Sequential Operation of Gates at the Molecular-Scale. J. Am. Chem. Soc, 1999,121:1393-1394.
[16]Roque A, Pina F, Alves S, et al.Micelle effect on the'write-lock-read-unlock-erase'cycle of 4'-hydroxyflavylium ion. J. Mater. Chem.,1999,9:2265-2270.
[17]Credi A, Balzani V, Langford S J, et al.Logic Operations at the Molecular Level. An XOR Gate Based on a Molecular Machine.J. Am. Chem, Soc,1997,119: 2679-2680.
[18]Pina F, Melo M J, Maestri M, et al. Artificial Chemical Systems Capable of Mimicking Some Elementary Properties of Neurons.J. Am. Chem. Soc,2000, 122:4496-4498.
[19]de Silva A P,Gunaratne H Q N, McCoy C P.A molecular photoionic AND gate based on fluorescent signalling. Nature,1993,364:42-44.
[20]Magri D C, Callan J F, de Silva A P,et al.The Anthracen-9-ylmethyloxy Unit: An Underperforming Motif Within the Fluorescent PET (Photoinduced Electron Transfer) Sensing Framework. Journal of Fluorescence,2005,75:769-775.
[21]Uchiyama S, McClean G D, Iwai K, et al.Membrane Media Create Small Nanospaces for Molecular Computation.J. Am. Chem. Soc,2005,127:8920-8921.
[22]Gust D, Moore T A, Moore A L. Molecular switches controlled by light. Chem. Commun.,2006,1169-1178.
[23]宗国强,吕功煊.基于N-(9-蒽甲基)-L-组氨酸的NOR荧光逻辑门.物理化学学报，2008,24：1902-1906.
[24]H Takakusa, K Kikuchi,Y Urano, S Sakamoto, et al., Design and Synthesis of an Enzyme-Cleavable Sensor Molecule for Phosphodiesterase Activity Based on Fluorescence Resonance Energy Transfer. J. Am.Chem. Soc;2002,124(8); 1653-1657.
[25]H Takakusa, K Kikuchi, Y Urano, H Kojima, T Nagano. A Novel Design Method of Ratiometric Fluorescent Probes Based on Fluorescence Resonance Energy Transfer Switching by Spectral Overlap Integral. Chem.Eur.J.,2003,9, No.71479-1485.
[26]Adachi C, Tsutsui T., Saito S., Blue light-emitting organic electroluminescent devices. Appl. Phys.Lett,1990,56,799.
[27]Bettenhausen J.Strohriegl P., Efficient synthesis of starburst oxadiazole compounds. Adv.Mater.,1996,8,507.
[28]Kido J., Nagai K., Okamoto Y., Skotheim T., Electroluminescence from Polysilane Film Doped with Europium Complex. Chem. Lett,1991,1267.
[29]卢勇,陈静对2-吡啶甲酰肼的合成研究.化学工程与装备，2006年第三期.
[30]Xin J. F.; Ma, J. Z. H.; Hang, S. F., Review of the Methods of Preparing Acyl Chlorides. HEBEI CHEMICAL ENGINEERING AND INDUSTRY,200629(11).
[31]Bentiss, F.; Lagrenee, M., RAPID SYNTHESIS OF 2,5-DISUBSTITUTED 1,3,4-OXADIAZOLES UNDER MICROWAVE IRRADIATION. Synth. Commun.,2001,31,935-938.
[32]李希晨,杨新玲,开振鹏,凌云,N-叔丁基苯基呋喃甲酰肼的合成研究,化学通报，2006年9期.
[33]余书强,芳酰基偶氮化合物和芳基酰肼的合成研究.[硕士学位论文].河南师范大学2004.
[34]J. M. Hoover, A. DiPasquale, J. M. Mayer, Platinum-Catalyzed Intramolecular Hydrohydrazination:Evidence for Alkene Insertion into a Pt-N Bond./. Am. Chem. Soc,2010,132 (14),5043-5053.
[35]Era M., Tsutsui T., Saito S., Organic-inorganic heterostructure electroluminescent device using a layered perovskite semiconductor (C6H5C2H4NH3)2Pbl4. Appl. Phys.Lett.,1994,65,676.
[36]Kido J.,Hayase H.,Hongawa K.,Nagai K.,Okuyama K.,Bright red light-emitting organic electroluminescent devices having a europium complex as an emitter. Appl. Phys. Lett,1994,65,2124.
[37]邱早早,含葡萄糖及苯并氮杂卓骨架的1,2,4-三唑、1,3,4-噁二唑、1,3,4-噻二唑杂环衍生物的合成及抗菌活性.[硕士学位论文].兰州大学2005.
[38]Mazzone G.,Puglisi G.,A new synthesis of symmetrical 2,5-diaryl-1,3,4-thiadiazoles.J.Heterocyclic chem.,1983,20,1399.
[39]Pedersen B.S.,Lawesson S.O.Studies on organophosphorus compounds—XXⅦ: Synthesis of thiono-, thiolo-and dithiolactones. Tetrahedron,1979,35,1339.
[40]Zoltan Kaleta, Brian T. Makowski.,Synthesis and Application of a Fluorous Lawesson's Reagent:Convenient Chromatography-Free Product Purification. Org. Lett, Vol.8, No.6,2006.1093-1095.
[41]Stephen F. M, David R. T., Thiadiazoles and thiadiazolines. Part 3. Synthesis of triazol-3-yl-A2-1,3,4-thiadiazolines and anew synthesis of unsymmetrical 2,5-di-substituted 1,3,4-thiadiazoles. J. CHEM. SOC. PERKIN TRANS I.,1982,1987.
[42]V. Polshettiwar, R. S.Varma.,Greener and rapid access to bio-active heterocycles:one-pot solvent-free synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles.Tetrahedron Letters 49(2008)879-883.
[43]V Balzani, Gomez-Lopez, J. F.Stoddart. Molecular Machines.Ace. Chem. Res.,1998,31:405-414.
[44]V Balzani, A. Credi, F.M.Raytno,Artificial Molecular Machines.Angew. Chem. Int. Ed.,2000,39:3348-3391.
[45]Raymo, F.M.Digital Processing and Communication with Molecular Switches. Adv. Mater.,2002,14:401.
[46]deSilva, A. P.;McClenaghan, N. D.Molecular-Scale Logic Gates.Chem. Eur. J., 2004,10:574.
[47]王文秀.一种选择性检测次氯酸的水溶性荧光分子探针.[硕士学位论文]延边大学化学系,2009.
[48]于海涛,新型有机电致发光材料的合成、结构表征及性质研究.[博士学位论文]南开大学化学系,2002.
[49]W. Lin, L. Long, L. Yuan, Z. Cao, J. Feng, A novel ratiometric fluorescent Fe3+ sensor based on a phenanthroimidazole chromophore. Analytica Chimica Acta., 2009,634,262-266.
[50]P. Healy, B, Skelton, A.white, Structural Studies in the Iron(Ⅲ)/Chloride/α,α Diimine System. Ⅲ*Crystal Structures of Tris(2,2'-bipyridine)iron(Ⅱ)μ-Oxo-bis[trichloroferrate(Ⅲ)] and of'Compound A',μ-Oxo-bis[cis-chlorobis-(1,10-phenanthroline)iron(Ⅲ)] Chloride Solvate. Aust:J. Chem.,1983,36,2057-2064,
[51]M.Collomb, A.Deronzier, K. Gorgy, J.Lepreutre, J.Pecaut, Electrochemical properties of [FeⅢ(L)2Cl2][PF6] and [Fe2Ⅲ,ⅢO(L)4Cl2][PF6]2 [L=2,2'-bipyridine (bpy)and 4,4'-dimethyl-2,2'-bipyridine (dmbpy)].Crystal structures of the dmbpy derivatives. New J. Chem.,1999,785-790.
[52]Zhao, Z. J.; Xing, Y. J.; Wang, Z. X.; Lu, P.Dual-Fluorescent Donor-Acceptor Dyad with Tercarbazole Donor and Switchable Imide Acceptor:Promising Structure for an Integrated Logic Gate. Org. Lett,2007,9:547.
[53]Guo, X. F.;Zhang, D. Q.; Zhang, G. X.;Zhu, D.B.,Monomolecular Logic:"Half-Adder" Based on Multistate/Multifunctional Photochromic Spiropyrans. J. Phys. Chem. B,2004,108:11942.
[54]Qu, D. H.; Ji, F. Y.; Wang, Q. C; Tian, H. A Double INHIBIT Logic Gate Employing Configuration and Fluorescence Changes. Adv. Mater.,2006,18:2035.
[55]Zhao, L.;Sui, D.;Chai, J.;Wang, Y.;Jiang, S.Digital Logic Circuit Based on a Single Molecular System of Salicylidene Schiff Base.J. Phys. Chem. B,2006, 110:24299.
[56]Wang, H. M.; Zhang, D. Q.; Guo, X. F.; Zhu, L. Y.,Tuning the fluorescence of 1-imino nitroxide pyrene with two chemical inputs:mimicking the performance of an "AND"gate. Chem. Commun.,2004:670.
[57]Zhou, X. Y.; Yu, B. R.; Zhang, H. H., Liu, W. S., Both Visual and Fluorescent Sensor for Zn2+Based on Quinoline Platform. Inorg. Chem.,2010,49,4002-4007.
[58]Peng, X. J.; Du, J. J.;Fan, J. L.;A Selective Fluorescent Sensor for Imaging Cd2+ In Living Cells.J. Am. Chem. Soc,2007,129,1500-1501.