基于芘荧光功能团探针的合成及性能研究
|
摘要
近年来人们针对生物体及环境中的一些特殊类别物质设计的识别探针已经被广泛研究。在这方面,尤其是对重金属及过渡金属如：Hg2+、Pb2+、Cd2+、Cu2+进行识别的化学探针尤为重要。而在这些探针的研究过程中,往往都存在着离子之间互相干扰的问题,尤其是Hg2+和Cu2+之间的相互干扰,基于这方面的限制,探针的选择性往往得不到很有效的突破。
芘基团作为一个非常好的荧光功能基团,由于其特殊的excimer性质,常常用于荧光探针的设计之中。本论文设计并合成了分别以吡啶-哌嗪为识别基团(Binding subunit),以芘为信号单元(Signalling subunit),通过酰胺基连接的结构的荧光探针(SCY-1和SCY-2),由最初原料芘经过硝基化、还原、氯乙酰化、胺化、溴代一系列反应合成得到目标产物,并通过1H NMR、13C NMR和HRMS等方式对其表征验证了结构的正确。
主要通过荧光发射光谱对探针SCY-1的monmer-excimer性质进行了系统研究,考察了对Hg2+和Cu2+的识别和区分效果并研究。结果表明,探针SCY-1适合于在中性和弱碱性作为金属离子的选择性识别。并且也研究了Hg2+和Cu2+与探针SCY-1的配位能力及配位方式,结果发现探针SCY-1与Hg2+的配位能力比Cu2+要强。探针SCY-1对汞离子和铜离子的检测限分别为1.2×10-6M和3.2×10-6M,并且都是以1：2的配位方式进行配位。
对于所合成出的探针SCY-2,由于溶解度差的限制,使测试无法进行,未能得出预期的对铜离子增强的效果。
The development of artificial receptors for the sensing and recognition of environmentally and biologically important species has been actively investigated in recent years. In this regard, chemosensors that can highly sensitively and selectively detect heavy and transition metal ions (HTM) such as Hg2+, Pb2+, Cd2+, and Cu2+ are especially important. In the course of the study of these probes, there is often mutual interference between the ions, especially between Hg2+ and Cu2+ mutual interference. Based on this constraint, the selectivity of the probe is often not very effective breakthrough.
In this dissertation, two probes (SCY-1) have been developed, in which pyridine-piperazine unit is utilized as binding subunit, pyrene as signaling subunit linked with amide group. Their chemical structures were characterized by 1HNMR,13CNMR and HRMS.
The monomer-excimer emission was studied with fluorescence emission spectra including the selective recognition of mercury and copper ions. It has also been demonstrated that SCY-1 is suitable for use in neutral and alkaline metal ions as selective recognition, and compounds SCY-1 and Hg2+ coordination ability and are stronger than Cu2+. The detection limit of SCY-1 to Hg2+ is 1.2×10-6M and that to Cu2+ is 3.2×10-6M. The coordinated ways of SCY-1 to the two ions are both 1:2.
For the limitation of solubility, the test of SCY-2 can not be conducted. We haven't achieve the expected effect.
芘基团作为一个非常好的荧光功能基团,由于其特殊的excimer性质,常常用于荧光探针的设计之中。本论文设计并合成了分别以吡啶-哌嗪为识别基团(Binding subunit),以芘为信号单元(Signalling subunit),通过酰胺基连接的结构的荧光探针(SCY-1和SCY-2),由最初原料芘经过硝基化、还原、氯乙酰化、胺化、溴代一系列反应合成得到目标产物,并通过1H NMR、13C NMR和HRMS等方式对其表征验证了结构的正确。
主要通过荧光发射光谱对探针SCY-1的monmer-excimer性质进行了系统研究,考察了对Hg2+和Cu2+的识别和区分效果并研究。结果表明,探针SCY-1适合于在中性和弱碱性作为金属离子的选择性识别。并且也研究了Hg2+和Cu2+与探针SCY-1的配位能力及配位方式,结果发现探针SCY-1与Hg2+的配位能力比Cu2+要强。探针SCY-1对汞离子和铜离子的检测限分别为1.2×10-6M和3.2×10-6M,并且都是以1：2的配位方式进行配位。
对于所合成出的探针SCY-2,由于溶解度差的限制,使测试无法进行,未能得出预期的对铜离子增强的效果。
The development of artificial receptors for the sensing and recognition of environmentally and biologically important species has been actively investigated in recent years. In this regard, chemosensors that can highly sensitively and selectively detect heavy and transition metal ions (HTM) such as Hg2+, Pb2+, Cd2+, and Cu2+ are especially important. In the course of the study of these probes, there is often mutual interference between the ions, especially between Hg2+ and Cu2+ mutual interference. Based on this constraint, the selectivity of the probe is often not very effective breakthrough.
In this dissertation, two probes (SCY-1) have been developed, in which pyridine-piperazine unit is utilized as binding subunit, pyrene as signaling subunit linked with amide group. Their chemical structures were characterized by 1HNMR,13CNMR and HRMS.
The monomer-excimer emission was studied with fluorescence emission spectra including the selective recognition of mercury and copper ions. It has also been demonstrated that SCY-1 is suitable for use in neutral and alkaline metal ions as selective recognition, and compounds SCY-1 and Hg2+ coordination ability and are stronger than Cu2+. The detection limit of SCY-1 to Hg2+ is 1.2×10-6M and that to Cu2+ is 3.2×10-6M. The coordinated ways of SCY-1 to the two ions are both 1:2.
For the limitation of solubility, the test of SCY-2 can not be conducted. We haven't achieve the expected effect.
引文
[1]Zhou, Y., Zhu, C. Y., Gao, X. S., You, X. Y., Yao, C. Hg2+-Selective Ratiometric and "Off-On" Chemosensor Based on the Azadiene-Pyrene Derivative [J]. Organic Letters.,2010,12(11):2566-2569
[2]Jiang, P. G., Chen, L. Z., Lin, J., Liu, Q., Ding, J., Gao, X., Guo, Z. J. Novel Zinc Fluorescent Probe Bearing Dansyl and Aminoquinoline Groups. Chem. Commun. 2002,1424-1425
[3]Zhang, H., Han, L. F., Zachariasse, K. A., Jiang, Y. B.8-Hydroxyquinoline Benzoates as Highly Sensitive Fluorescent Chemosensors for Transition Metal Ions. Org. Lett.2005,7(19):4217-4420
[4]He, Q., Miller, E. W., Wong, A. P., Chang, C. J. A Selective Fluorescent Sensor for Detecting Lead in Living Cells. J. Am. Chem. Soc.2006,128(29):9316-9317
[5]Martinez, R., Zapata, F., Caballero, A., Espinosa, A., Tairraga, A., Molina, P. 2-Aza-1,3-butadiene Derivatives Featuring an Anthracene or Pyrene Unit:Highly Selective Colorimetric and Fluorescent Signaling of Cu2+ Cation. Org. Lett.2006, 8(15):3235-3238
[6]Avirah, R. R., Jyothish, K., Ramaiah, D. Dual-Mode Semisquaraine-Based Sensor for Selective Detection of Hg2+ in a Micellar Medium. Org. Lett.2007,9(1):121-124
[7]Yoon, S., Miller, E. W., He, Q., Do, P. H., Chang, C. J. A Bright and Specific Fluorescent Sensor for Mercury in Water, Cells, and Tissue. Angew. Chem., Int. Ed. 2007,46, (35):6558-6661
[8]Shiraishi, Y., Maehara, H., Ishizumi, K., Hirai, T. Hg (Ⅱ)-Selective Excimer Emission of a Bisnaphthyl Azadiene Derivative. Org. Lett.2007,9(16):3125-3128
[9]Nolan, E. M., Lippard, S. J. A "Turn-On" Fluorescent Sensor for the Selective Detection of Mercuric Ion in Aqueous Media. J. Am. Chem. Soc.2003,125(47): 14270-14271
[10]Zhang, D., Yin, S., Shuai, Z., Zhu, D. 1,3-Dithiole-2-thione Derivatives Featuring an Anthracene Unit:New Selective Chemodosimeters for Hg(II) Ion. Chem. Commun. 2005(16):2161-2163
[11]Yoon, S., Albers, A. E., Wong, A. P., Chang, C. J. Screening Mercury Levels in Fish with a Selective Fluorescent Chemosensor. J. Am. Chem. Soc.2005,127(46): 16030-16031
[12]Guliyev, R., Coskun, A., Akkaya, E. U. Design Strategies for Ratiometric Chemosensors:Modulation of Excitation Energy Transfer at the Energy Donor Site. J. Am. Chem. Soc.,2009,131(25):9007-9013
[13]Xu, Z. C., Yoon, J. Y., Spring, D. R. Fluorescent Chemosensors for Zn2+. Chem. Soc. Rev.2010,39(6):1996-2006
[14]Thomas, S. W., Joly, G. D., Swager, T. M. Chemical Sensors Based on Amplifying Fluorescent Conjugated Polymers. Chem. Soc. Rev.2007,107(4):1339-1352
[15]Martinez-Mannez, R., Sancenon, F. Transition-Metal-Catalyzed Reactions in Steroid Synthesis. Chem. Rev.,2003,103(10):4119-4130
[16]de Silva, A. P., Nimal Gunaratne, H. Q., Gunnlaugsson, T., Huxley, A. J. M., McCoy, C. P., Rademacher, J. T., Rice, T. E. Introduction:Molecular Recognition. Chem. Rev.1997,97(5):1515-1566
[17]Xu, Z., Chen, X., Kim, H. N., Yoon., J. Sensors for the Optical Detection of Cyanide Ion. Chem. Soc. Rev.2010,39(1):127-145
[18]Que, E. L., Domaille, D. W., Chang, C. J. Metals in Neurobiology:Probing Their Chemistry and Biology with Molecular Imaging. Chem. Rev.2008,108(5): 1517-1549
[19]Li, G., Xu, Z., Chen, C., Huang, Z. A Highly Efficient and Selective Turn-on Fluorescent Sensor for Cu2+ Ion Based on Calix arene Bearing Four Iminoquinoline Subunits on the Upper Rim. Chem. Commun.,2008,21(15):1774-1776
[20]Swamy, K. M. K., Ko, S. K., Kwon. S. K., Lee, H. N., Mao, C., Kim, J. M., Yoon, J. Boronic Acid-linked Fluorescent and Colorimetric Probes for Copper Ions. Chem. Commun.,2008(45):5915-5917
[21]Zhou, Y., Wang, F., Kim, Y., Kim, S.-J., and Yoon, J. Cu2+-Selective Ratiometric and "Off-On" Sensor Based on the Rhodamine Derivative Bearing Pyrene Group. Org. Lett.,2009,11(19):4442-4445
[22]Chan, W. C., Nie, S. Quantum Dot Bioconjugates for Ultrasensitive Nonisotopic Detection. Science.1998,281(10):2016-2018
[23]Michalet, X., Pinaud, F. F., Bentolila, L. A., Tsay, J. M., Doose, S., Li, J. J., Sundaresan, G., Wu, A. M., Gambhir, S. S., Weiss, S. Quantum Dots for Live Cells, in Vivo Imaging, and Diagnostics. Science.2005,307(5709):538-544
[24]Derfus, A. M., Chan, W. C. W., Bhatia, S. N. Probing the Cytotoxicity of Semiconductor Quantum Dots. Nano Lett.2004,4(1):11-18
[25]Hama, Y., Urano, Y., Koyama, Y., Bernardo, M., Choyke, P. L., Kobayashi, H. A Comparison of the Emission Efficiency of Four Common Green Fluorescence Dyes after Internalization into Cancer Cells. Bioconjugate Chem.2006,17(6):1426-1431
[26]Kobayashi, Hisataka,O., Mikako, A., Raphael, C., Peter, L. U., Yasuteru. New Strategies for Fluorescent Probe Design in Medical Diagnostic Imaging. Chem. Rev. 2010,110(5):2620-2640
[27]Zhou, W. D., Li, Y. J., Li, Y. L., Zhu, D. B. Pyrene-Based Dual-Mode Fluorescence Switches and Logic Gate That Function in Solution and Film. Chem. Asia.2006, 1(2):224-230
[28]de Silva, A. P., Gunaratne, H. Q. N., Gunnlaugsson, T., Huxley, A. J. M., McCoy, C. P. Signaling Recognition Events with Fluorescent Sensors and Switches. Chem. Rev. 1997,97(5):1515-1566
[29]Fabbrizzi, L., Licchelli, M., Pallavicini, P. Transition Metals as Switches. Acc. Chem. Res.1999,32(10):846-853
[30]Feringa, B. L., Molecular Switches.[M] Wiley-VCH, Weinheim,2001
[31]Balzani, V., Credi, A., Raymo, F. M., Stoddart, J. F. Kunstliche molekulare Maschinen. Angew. Chem.2000,112(19):3484-3530
[32]Balzani, V., Credi, A., Langford, S. J., Raymo, F. M., Stoddart, J. F., Venturi, M. Light-Driven Molecular Rotor:Unidirectional Rotation Controlled by a Single Stereogenic Center. J. Am. Chem. Soc.2000,122(48):3542-3543
[33]Cao, Y. D., Zheng, Q. Y., Chen, C. F., Huang, Z. T. A New Fluorescent Chemosensor for Transition Metal Cations and on/off Molecular Switch Controlled by pH. Tetrahedron Lett.2003,44(25):4751-4755
[34]Uchiyama, S., N. Kawai, A. P. de Silva, K. Iwai. Fluorescent Polymeric AND Logic Gate with Temperature and pH as Inputs. J. Am. Chem. Soc.2004,126(10): 3032-3033
[35]Gobbi, L., Seiler, P., Diederich, F. Ein Neuer Dreifacher Chromophorer Molekularer Schalter:pH- und Lichtabhngige Schaltcyclen. Angew. Chem.1999,111(5): 737-740
[36]Zhang, G., Zhang, D., Guo, X., Zhu, D. A New Redox-Fluorescence Switch Based on a Triad with Tetrathiafulvalene and Anthracene Units. Org. Lett.2004,6(8):1209-1212
[37]de Silva, S. A., Amorelli, B., Isidor, D. C., Loo, K. C., Crooker, K. E., Pena,Y. E. A Fluorescent 'off-on-off' Proton Switch with an Overriding 'Enable-disable' Sodium Ion Switch. Chem. Commun.2002(13):1360-1361
[38]Qu, D. H., Wang, Q. C., Ren, J., Tian, H. A Light-Driven Rotaxane Molecular Shuttle with Dual Fluorescence Addresses. Org. Lett.2004,6(13):2085-2088
[39]Shiraishi, Y., Tokitoh, Y., Nishi-mura, G., Hirai, T. A Molecular Switch with pH-Controlled Absolutely Switchable Dual-Mode Fluorescence. Org. Lett.2005, 7(13):2611-2614
[40]Moon, S. Y., Youn, N. J., Park, S. M., Chang, S. K. Diametrically Disubstituted Cyclam Derivative Having Hg2+-Selective Fluoroionophoric Behaviors. J. Org. Chem.2005,70(6):2394-2397
[41]Guo, X., Zhang, D., Wang, T., Zhu, D. Reversible Regulation of Pyrene Excimer Emission by Light and Metal ions in the Presence of Photochromic Spiropyran: Toward Creation of a New Molecular Logic Circuit. Chem. Commun.2003(7): 914-915
[42]Xu, Z. C., Yoon, J. Y., Spring, D. R. A Selective and Ratiometric Cu2+ Fluorescent Probe Based on Naphthalimide Excimer-monomer Switching. Chem. Commun.2010, 46(15):2563-2565
[43]Xu, Z., Xiao, Y., Qian, X., Cui J. and Cui, D. Ratiometric and Selective Fluorescent Sensor for Cull Based on Internal Charge Transfer (ICT). Org. Lett.,2005,7(5): 889-892
[44]Xu, Z., Qian, X., and Cui, J. Colorimetric and Ratiometric Fluorescent Chemosensor with a Large Red-Shift in Emission:Cu (Ⅱ)-Only Sensing by Deprotonation of Secondary Amines as Receptor Conjugated to Naphthalimide Fluorophore. Org. Lett. 2005,7(14):3029-3032
[45]Yang, H., Liu, Z., Zhou, Z., Shi, E., and Li, F. Highly Selective Ratiometric Fluorescent Sensor for Cu (Ⅱ) with Two Urea Groups. Tetrahedron Lett.2006, 47(17):2911-2914
[46]Xu, Z., Pan, J., Spring, D. R., Cui, J., and Yoon, J. Ratiometric Fluorescent and Colorimetric Sensors for Cu2+ Based on 4,5-disubstituted-1,8-naphthalimide and Sensing Cyanide via Cu2+ Displacement Approach. Tetrahedron.2010,66(9): 1678-1683
[47]Kim, H., Park, S., Yoon, S., and Kim, J. S. FRET-derived Ratiometric Fluorescence Sensor for Cu2+. Tetrahedron.2008,64(7):1294-1300
[48]Kim, H., Hong, J., Hong, A., Ham, S., Lee, J., and Kim, J. S. Cu2+-Induced Intermolecular Static Excimer Formation of Pyrenealkylamine. Org. Lett.2008, 10(10):1963-1966
[49]Jung, H., Park, M., Han, D., Kim, E., Lee, C., Ham, S., and Kim, J. S. Cu2+ Ion-Induced Self-Assembly of Pyrenylquinoline with a Pyrenyl Excimer Formation. Org. Lett.2009,11(10):3378-3381
[50]Lin, W., Yuan, L., Tan, W., Feng, J., and Long, L. A Sensitive and Selective Fluorescent Thiol Probe in Water Based on the Conjugate 1,4-Addition of Thiols to,β-Unsaturated Ketones. Chem.-Eur. J.2009,15(20):5096-5103
[51]Xu, Z., Han, S., Lee, C., Yoon, J., and Spring, D. R. Development of Off-on Fluorescent Probes for Heavy and Transition Metal Ions. Chem. Commun.2010, 46(10):1679-1681
[52]Zhao, Q. Li, F. Y., Huang, C. H. Phosphorescent Chemosensors Based on Heavy-metal Complexes. Chem. Soc. Rev.2010,39(8):3007-3030
[53]Kim, J. H., Hwang, A.-R., Chang, S.-K. Hg2+-selective fluoroionophore of p-tert-butylcalix arene-diaza-crown Ether Having Pyrenylacetamide Subunits. Tetrahedron Lett.2004,45(11):7557-7561
[54]Kim, S. H., Song, K. C., Ahn, S., Kang, Y. S., Chang, S.-K. Hg2+-selective Fluoroionophoric Behavior of Pyrene Appended Diazatetrathia-crown Ethe. Tetrahedron Lett.2006,47(4):497-500
[55]Nolan, Elizabeth, M., Lippard, Stephen, J. Tools and Tactics for the Optical Detection of Mercuric Ion. Chem. Rev.2008,108(9):3443-3480
[56]Liu, L., Zhang, G. X., Xiang, J. F., Zhang, D. Q., and Zhu, D. B. Fluorescence "Turn On" Chemosensors for Ag+ and Hg2+ Based on Tetraphenylethylene Motif Featuring Adenine and Thymine Moieties. Org. Lett.2008,10(20):4581-4584
[57]Miyata, O., Takahashi, S., Tamura, A., Ueda, M., Naito, T. Novel synthesis of substituted pyrrolidines and piperidines via radical addition-ionic cyclization reaction of oxime ethers. Tetrahedron.2008,64(7):1270-1284
[58]Guo, X. F., Qian, X. H., Jia, L. H. A Highly Selective and Sensitive Fluorescent Chemosensor for Hg2+ in Neutral Buffer Aqueous Solution. J. Am. Chem. Soc. 2004,126(8):2272-2273
[59]Hassani, M., Cai, Wen, Holley, D. C. Novel Lavendamycin Analogues as Antitumor Agents:Synthesis, in Vitro Cytotoxicity, Structure-Metabolism, and Computational Molecular Modeling Studies with NAD (P) H:Quinone Oxidoreductase 1. J. Med. Chemistry.2005,48(24):7743-7749
[60]Yasuhiro, S., Chizuru, I., Takayuki, Hirai. A Quinoline-polyamine Conjugate as a Fluorescent Chemosensor for Quantitative Detection of Zn (Ⅱ) in Water. Tetrahedron Lett.2007,48(44):7769-7773
[2]Jiang, P. G., Chen, L. Z., Lin, J., Liu, Q., Ding, J., Gao, X., Guo, Z. J. Novel Zinc Fluorescent Probe Bearing Dansyl and Aminoquinoline Groups. Chem. Commun. 2002,1424-1425
[3]Zhang, H., Han, L. F., Zachariasse, K. A., Jiang, Y. B.8-Hydroxyquinoline Benzoates as Highly Sensitive Fluorescent Chemosensors for Transition Metal Ions. Org. Lett.2005,7(19):4217-4420
[4]He, Q., Miller, E. W., Wong, A. P., Chang, C. J. A Selective Fluorescent Sensor for Detecting Lead in Living Cells. J. Am. Chem. Soc.2006,128(29):9316-9317
[5]Martinez, R., Zapata, F., Caballero, A., Espinosa, A., Tairraga, A., Molina, P. 2-Aza-1,3-butadiene Derivatives Featuring an Anthracene or Pyrene Unit:Highly Selective Colorimetric and Fluorescent Signaling of Cu2+ Cation. Org. Lett.2006, 8(15):3235-3238
[6]Avirah, R. R., Jyothish, K., Ramaiah, D. Dual-Mode Semisquaraine-Based Sensor for Selective Detection of Hg2+ in a Micellar Medium. Org. Lett.2007,9(1):121-124
[7]Yoon, S., Miller, E. W., He, Q., Do, P. H., Chang, C. J. A Bright and Specific Fluorescent Sensor for Mercury in Water, Cells, and Tissue. Angew. Chem., Int. Ed. 2007,46, (35):6558-6661
[8]Shiraishi, Y., Maehara, H., Ishizumi, K., Hirai, T. Hg (Ⅱ)-Selective Excimer Emission of a Bisnaphthyl Azadiene Derivative. Org. Lett.2007,9(16):3125-3128
[9]Nolan, E. M., Lippard, S. J. A "Turn-On" Fluorescent Sensor for the Selective Detection of Mercuric Ion in Aqueous Media. J. Am. Chem. Soc.2003,125(47): 14270-14271
[10]Zhang, D., Yin, S., Shuai, Z., Zhu, D. 1,3-Dithiole-2-thione Derivatives Featuring an Anthracene Unit:New Selective Chemodosimeters for Hg(II) Ion. Chem. Commun. 2005(16):2161-2163
[11]Yoon, S., Albers, A. E., Wong, A. P., Chang, C. J. Screening Mercury Levels in Fish with a Selective Fluorescent Chemosensor. J. Am. Chem. Soc.2005,127(46): 16030-16031
[12]Guliyev, R., Coskun, A., Akkaya, E. U. Design Strategies for Ratiometric Chemosensors:Modulation of Excitation Energy Transfer at the Energy Donor Site. J. Am. Chem. Soc.,2009,131(25):9007-9013
[13]Xu, Z. C., Yoon, J. Y., Spring, D. R. Fluorescent Chemosensors for Zn2+. Chem. Soc. Rev.2010,39(6):1996-2006
[14]Thomas, S. W., Joly, G. D., Swager, T. M. Chemical Sensors Based on Amplifying Fluorescent Conjugated Polymers. Chem. Soc. Rev.2007,107(4):1339-1352
[15]Martinez-Mannez, R., Sancenon, F. Transition-Metal-Catalyzed Reactions in Steroid Synthesis. Chem. Rev.,2003,103(10):4119-4130
[16]de Silva, A. P., Nimal Gunaratne, H. Q., Gunnlaugsson, T., Huxley, A. J. M., McCoy, C. P., Rademacher, J. T., Rice, T. E. Introduction:Molecular Recognition. Chem. Rev.1997,97(5):1515-1566
[17]Xu, Z., Chen, X., Kim, H. N., Yoon., J. Sensors for the Optical Detection of Cyanide Ion. Chem. Soc. Rev.2010,39(1):127-145
[18]Que, E. L., Domaille, D. W., Chang, C. J. Metals in Neurobiology:Probing Their Chemistry and Biology with Molecular Imaging. Chem. Rev.2008,108(5): 1517-1549
[19]Li, G., Xu, Z., Chen, C., Huang, Z. A Highly Efficient and Selective Turn-on Fluorescent Sensor for Cu2+ Ion Based on Calix arene Bearing Four Iminoquinoline Subunits on the Upper Rim. Chem. Commun.,2008,21(15):1774-1776
[20]Swamy, K. M. K., Ko, S. K., Kwon. S. K., Lee, H. N., Mao, C., Kim, J. M., Yoon, J. Boronic Acid-linked Fluorescent and Colorimetric Probes for Copper Ions. Chem. Commun.,2008(45):5915-5917
[21]Zhou, Y., Wang, F., Kim, Y., Kim, S.-J., and Yoon, J. Cu2+-Selective Ratiometric and "Off-On" Sensor Based on the Rhodamine Derivative Bearing Pyrene Group. Org. Lett.,2009,11(19):4442-4445
[22]Chan, W. C., Nie, S. Quantum Dot Bioconjugates for Ultrasensitive Nonisotopic Detection. Science.1998,281(10):2016-2018
[23]Michalet, X., Pinaud, F. F., Bentolila, L. A., Tsay, J. M., Doose, S., Li, J. J., Sundaresan, G., Wu, A. M., Gambhir, S. S., Weiss, S. Quantum Dots for Live Cells, in Vivo Imaging, and Diagnostics. Science.2005,307(5709):538-544
[24]Derfus, A. M., Chan, W. C. W., Bhatia, S. N. Probing the Cytotoxicity of Semiconductor Quantum Dots. Nano Lett.2004,4(1):11-18
[25]Hama, Y., Urano, Y., Koyama, Y., Bernardo, M., Choyke, P. L., Kobayashi, H. A Comparison of the Emission Efficiency of Four Common Green Fluorescence Dyes after Internalization into Cancer Cells. Bioconjugate Chem.2006,17(6):1426-1431
[26]Kobayashi, Hisataka,O., Mikako, A., Raphael, C., Peter, L. U., Yasuteru. New Strategies for Fluorescent Probe Design in Medical Diagnostic Imaging. Chem. Rev. 2010,110(5):2620-2640
[27]Zhou, W. D., Li, Y. J., Li, Y. L., Zhu, D. B. Pyrene-Based Dual-Mode Fluorescence Switches and Logic Gate That Function in Solution and Film. Chem. Asia.2006, 1(2):224-230
[28]de Silva, A. P., Gunaratne, H. Q. N., Gunnlaugsson, T., Huxley, A. J. M., McCoy, C. P. Signaling Recognition Events with Fluorescent Sensors and Switches. Chem. Rev. 1997,97(5):1515-1566
[29]Fabbrizzi, L., Licchelli, M., Pallavicini, P. Transition Metals as Switches. Acc. Chem. Res.1999,32(10):846-853
[30]Feringa, B. L., Molecular Switches.[M] Wiley-VCH, Weinheim,2001
[31]Balzani, V., Credi, A., Raymo, F. M., Stoddart, J. F. Kunstliche molekulare Maschinen. Angew. Chem.2000,112(19):3484-3530
[32]Balzani, V., Credi, A., Langford, S. J., Raymo, F. M., Stoddart, J. F., Venturi, M. Light-Driven Molecular Rotor:Unidirectional Rotation Controlled by a Single Stereogenic Center. J. Am. Chem. Soc.2000,122(48):3542-3543
[33]Cao, Y. D., Zheng, Q. Y., Chen, C. F., Huang, Z. T. A New Fluorescent Chemosensor for Transition Metal Cations and on/off Molecular Switch Controlled by pH. Tetrahedron Lett.2003,44(25):4751-4755
[34]Uchiyama, S., N. Kawai, A. P. de Silva, K. Iwai. Fluorescent Polymeric AND Logic Gate with Temperature and pH as Inputs. J. Am. Chem. Soc.2004,126(10): 3032-3033
[35]Gobbi, L., Seiler, P., Diederich, F. Ein Neuer Dreifacher Chromophorer Molekularer Schalter:pH- und Lichtabhngige Schaltcyclen. Angew. Chem.1999,111(5): 737-740
[36]Zhang, G., Zhang, D., Guo, X., Zhu, D. A New Redox-Fluorescence Switch Based on a Triad with Tetrathiafulvalene and Anthracene Units. Org. Lett.2004,6(8):1209-1212
[37]de Silva, S. A., Amorelli, B., Isidor, D. C., Loo, K. C., Crooker, K. E., Pena,Y. E. A Fluorescent 'off-on-off' Proton Switch with an Overriding 'Enable-disable' Sodium Ion Switch. Chem. Commun.2002(13):1360-1361
[38]Qu, D. H., Wang, Q. C., Ren, J., Tian, H. A Light-Driven Rotaxane Molecular Shuttle with Dual Fluorescence Addresses. Org. Lett.2004,6(13):2085-2088
[39]Shiraishi, Y., Tokitoh, Y., Nishi-mura, G., Hirai, T. A Molecular Switch with pH-Controlled Absolutely Switchable Dual-Mode Fluorescence. Org. Lett.2005, 7(13):2611-2614
[40]Moon, S. Y., Youn, N. J., Park, S. M., Chang, S. K. Diametrically Disubstituted Cyclam Derivative Having Hg2+-Selective Fluoroionophoric Behaviors. J. Org. Chem.2005,70(6):2394-2397
[41]Guo, X., Zhang, D., Wang, T., Zhu, D. Reversible Regulation of Pyrene Excimer Emission by Light and Metal ions in the Presence of Photochromic Spiropyran: Toward Creation of a New Molecular Logic Circuit. Chem. Commun.2003(7): 914-915
[42]Xu, Z. C., Yoon, J. Y., Spring, D. R. A Selective and Ratiometric Cu2+ Fluorescent Probe Based on Naphthalimide Excimer-monomer Switching. Chem. Commun.2010, 46(15):2563-2565
[43]Xu, Z., Xiao, Y., Qian, X., Cui J. and Cui, D. Ratiometric and Selective Fluorescent Sensor for Cull Based on Internal Charge Transfer (ICT). Org. Lett.,2005,7(5): 889-892
[44]Xu, Z., Qian, X., and Cui, J. Colorimetric and Ratiometric Fluorescent Chemosensor with a Large Red-Shift in Emission:Cu (Ⅱ)-Only Sensing by Deprotonation of Secondary Amines as Receptor Conjugated to Naphthalimide Fluorophore. Org. Lett. 2005,7(14):3029-3032
[45]Yang, H., Liu, Z., Zhou, Z., Shi, E., and Li, F. Highly Selective Ratiometric Fluorescent Sensor for Cu (Ⅱ) with Two Urea Groups. Tetrahedron Lett.2006, 47(17):2911-2914
[46]Xu, Z., Pan, J., Spring, D. R., Cui, J., and Yoon, J. Ratiometric Fluorescent and Colorimetric Sensors for Cu2+ Based on 4,5-disubstituted-1,8-naphthalimide and Sensing Cyanide via Cu2+ Displacement Approach. Tetrahedron.2010,66(9): 1678-1683
[47]Kim, H., Park, S., Yoon, S., and Kim, J. S. FRET-derived Ratiometric Fluorescence Sensor for Cu2+. Tetrahedron.2008,64(7):1294-1300
[48]Kim, H., Hong, J., Hong, A., Ham, S., Lee, J., and Kim, J. S. Cu2+-Induced Intermolecular Static Excimer Formation of Pyrenealkylamine. Org. Lett.2008, 10(10):1963-1966
[49]Jung, H., Park, M., Han, D., Kim, E., Lee, C., Ham, S., and Kim, J. S. Cu2+ Ion-Induced Self-Assembly of Pyrenylquinoline with a Pyrenyl Excimer Formation. Org. Lett.2009,11(10):3378-3381
[50]Lin, W., Yuan, L., Tan, W., Feng, J., and Long, L. A Sensitive and Selective Fluorescent Thiol Probe in Water Based on the Conjugate 1,4-Addition of Thiols to,β-Unsaturated Ketones. Chem.-Eur. J.2009,15(20):5096-5103
[51]Xu, Z., Han, S., Lee, C., Yoon, J., and Spring, D. R. Development of Off-on Fluorescent Probes for Heavy and Transition Metal Ions. Chem. Commun.2010, 46(10):1679-1681
[52]Zhao, Q. Li, F. Y., Huang, C. H. Phosphorescent Chemosensors Based on Heavy-metal Complexes. Chem. Soc. Rev.2010,39(8):3007-3030
[53]Kim, J. H., Hwang, A.-R., Chang, S.-K. Hg2+-selective fluoroionophore of p-tert-butylcalix arene-diaza-crown Ether Having Pyrenylacetamide Subunits. Tetrahedron Lett.2004,45(11):7557-7561
[54]Kim, S. H., Song, K. C., Ahn, S., Kang, Y. S., Chang, S.-K. Hg2+-selective Fluoroionophoric Behavior of Pyrene Appended Diazatetrathia-crown Ethe. Tetrahedron Lett.2006,47(4):497-500
[55]Nolan, Elizabeth, M., Lippard, Stephen, J. Tools and Tactics for the Optical Detection of Mercuric Ion. Chem. Rev.2008,108(9):3443-3480
[56]Liu, L., Zhang, G. X., Xiang, J. F., Zhang, D. Q., and Zhu, D. B. Fluorescence "Turn On" Chemosensors for Ag+ and Hg2+ Based on Tetraphenylethylene Motif Featuring Adenine and Thymine Moieties. Org. Lett.2008,10(20):4581-4584
[57]Miyata, O., Takahashi, S., Tamura, A., Ueda, M., Naito, T. Novel synthesis of substituted pyrrolidines and piperidines via radical addition-ionic cyclization reaction of oxime ethers. Tetrahedron.2008,64(7):1270-1284
[58]Guo, X. F., Qian, X. H., Jia, L. H. A Highly Selective and Sensitive Fluorescent Chemosensor for Hg2+ in Neutral Buffer Aqueous Solution. J. Am. Chem. Soc. 2004,126(8):2272-2273
[59]Hassani, M., Cai, Wen, Holley, D. C. Novel Lavendamycin Analogues as Antitumor Agents:Synthesis, in Vitro Cytotoxicity, Structure-Metabolism, and Computational Molecular Modeling Studies with NAD (P) H:Quinone Oxidoreductase 1. J. Med. Chemistry.2005,48(24):7743-7749
[60]Yasuhiro, S., Chizuru, I., Takayuki, Hirai. A Quinoline-polyamine Conjugate as a Fluorescent Chemosensor for Quantitative Detection of Zn (Ⅱ) in Water. Tetrahedron Lett.2007,48(44):7769-7773
© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号 地址：北京市海淀区学院路29号 邮编：100083 电话：办公室：(+86 10)66554848；文献借阅、咨询服务、科技查新：66554700 |