Синтез и исследование хемосенсоров с антраценовым флурофором на катионы переходных металлов

Список литературы

1. Krakowiak K.E., Izatt R.M., Bradshow J.S. One-Step Syntheses of Macrocyclic Compounds: A Short Rewiew. // J. Heterocyclic Chem., 2001. v.38. № 1112. p. 1239−1248
2. Lohr H.-G., Vogtle F. Chromo- and Fluoroionophores. // Acc. Chem. Res., 1985. v, 18.p.65−72
3. Брень В.А. Флуоресцентные и фотохромные хемосенсоры. // Успехи химии. 2001.Т.70. № 12. с. 1152−1174
4. Montalti M., Prodi L., Zaccheroni N. Luminescent Chemosensors for Metal Ions. In Handbook of Photochemistry and Photobiology (Ed. Nalwa H.S.) // ASP, С A- Stevenson Ranch, 2003, p. 271−317
5. Heyen K.V., Cielen E., Tahri A., Saleh A., Boens N., Hoornaet G.L. Synthesis and Characterization Na+ and K+ indicators. // Tetrahedron., 1999. v.55. № 16. p. 5207−5226
6. Shin E. J. Mg -Selective Fluorescence Enhancement of Benzo-15-crown-5 Derivative Bearing Vinylanthracene Fluorophore. // Chem. Lett., 2002. p.686−687
7. Rurack K., Resch-Genger U., Rettig W. Unusually High Cation-Induced Fluorescence Enhancement of a Structurally Simple Intrinsic Fluoroiono-phore with a Donor-Acceptor-Donor Constitution. // Chem. Commun., 2000, p. 407−408
8. Jiang H., Xu H.J., Zhou Q.F. Synthesis and Effect of Cation Binding on Pho-tophysical Properties of l, 8-Anthraceno-18-Crown-5. // Chin. Chem. Lett., 1999, v.10. № 12. p.1015−1018
9. Kubo K., Sakaguchi S., Sakurai T. Synthesis, complexation, and fluorescence behavior of armed crown ethers carrying naphthyl group. // Talanta, 1999. v.49. p. 735−744
10. Erk C., Gocmen A. Cation complexing of crown ethers using fluorescence spectroscopy. Part II. // Talanta, 2000. v.53. № 1. p.137−140.
11. Erk C., Bulut M., Gocen A. The synthesis of novel crown ethers. Part VII. Coumarin derivatives of benzocrowns and cation binding from fluorescence spectra. // J. of Inclusion Phenomena, 2000. v.37. № 1. p.441−450.
12. Xia W.-S., Sehmehl R.H., Li C.-J. A Fluorescent 18-crown-6 based luminescence sensor for Lanthanide ions. // Tetrahedron, 2000. v.56. № 36. p. 70 457 049
13. Montalti M., Prodi L., Zaccheroni N. Luminescent Chemosensors Based on Anthracene or Dioxyxanthone Derivatives. // J. Fluoresc., 2000. v. 10. №.2. p. 71−76
14. Desvergne J.-P., Fages F., Bouas-Laurent H., Marsau P. Tunable photore-sponsive supramolecular systems. // Pure and Appl. Chem., 1999. v.64. № 9. p. 1231−1238
15. Marquis D., Desvergne J.-P. A cooperative effects in sodium cation com-plexation by a macrocyclic bis (9,10)anthraceno-crown ether in the ground state and in the excited state. // Chem. Phys. Lett., 1994. v.230. p. 131−136
16. Marquis D., Desvergne J.-P., Bouas-Laurent H. Photoresponsive Supramolecular Systems: Synthesis and Photophysical and Photochemical Study of Bis-(9,10-anthracenediyl)coronands AAOnOn. // J. Org. Chem., 1995. v.60. № 24. p.7984−7996
17. De Santis G., Fabbrizzi L., Licchelli M., Mangano C., Sacchi D. Redox Switching of Anthracene Fluorescence through the CuII/CuI Couple. // Inorg. Chem., 1995. v.34. № 14. p.3581−3582
18. Bergonzi R., Fabbrizzi L., Licchelli M. Molecular switches of fluorescent operating through metal centred redox couples. // Coord. Chem. Rev., 1998. v.170. p. 31−46
19. Kubo K., Kato N., Sakura T. Synthesis and Complexation Behavior of Diaza-18-crown-6 Carrying Two Pyrenylmethyl Groups. // Bull. Chem. Soc. Jpn., 1997. v.70. p. 3041−3046
20. Kubo K., Ishige R., Kubo J., Sakurai T. Synthesis and complexation behavior of N-(l-naphthylmethyl)-l, 4,7,10,13-pentaoxa-16-azacyclooctadecane. // 7b-lanta, 1999. v.48. p. 181−187
21. Charles S., Dubois F., Yunus S., Vander Donckt E. Determination by Fluorescence Spectroscopy of Cadmium at the Subnanomolar Level: Application to Seawater. II J. Fluoresc., 2000. v.10. №.2. p. 99−105
22. Kubo K., Sakurai T. Molecular Recognition of PET fluoroionophores. // Heterocycles, 2000. v.52. № 2. p. 945−976
23. Li H.-F., Dabestani R., Brown G.B., Hettich R.L. Spacer Length Effect on the Photoinduced Electron Transfer Fluorescent Probe for Alkali Metal Ions. // Photochem. Photobiol., 1999. v.69. p.513
24. Kim S. K., Bang M. Y., Lee S.-H., Nakamura K., Cho S.-W., Yoon J. New Fluorescent Chemosensors for Cationic Guests: l, 8-Bis (azacrown)anthra-cenes. // J. Inch Phenom. Macrocycl. Chem., 2002. v.43. p. 71−75
25. Kubo K., Ishige R., Sakurai T. Synthesis and complexation behavior of N, N-bis (9-anthrylmethyl)-1,4,10,13-Tetraoxa-7,16-diazacyclooctadecane. // Het-erocycles, 1998. v.48. № 2. p. 347−351
26. He H., Mortellaro M.A., Leiner M.J.P., Young S.T., Fraatz R.J., Tusa J. К. A Fluorescent Chemosensors for Sodium Based on Photoinduced Electron Transfer. If Anal. Chem., 2003. v.75. № 3. p. 549−555
27. Gunnlaugsson Т., Bichell В., Nolan C. A novel fluorescent photoinduced electron transfer (PET) sensor for lithium. // Tetrahedron Lett., 2002. v.43. p. 4989−4992
28. Kubo K., Ishige R., Sakurai T. Complexation and fluorescence behavior of di-azacrown ether carrying two anthryl pendants. // Talanta, 1999. v.49. p. 339— 344
29. Tucker J. H. R., Bouas-Laurent H., Marsau P., Riley S.W., Desvergne J.-P. A Novel crown ether-cryptand photos witch. // Chem. Commun., 1997. p. 11 651 166
30. Rurack K., Resch-Genger U. Rigidization, preorganization and electronic decoupling the 'magic triangle' for he design of highly efficient fluorescent sensors and switches. // Chem. Soc. Rev., 2002. v. 31. p. 116−127
31. Prodi L., Bolletta F., Montalti M., Zaccheroni N., Savage P.B., Bradshow J.S., Izatt R.M. A fluorescent sensor for magnesium ions. // Tetrahedron Lett., 1998. v.39. № 31. p. 5451−5453
32. Prodi L., Bargossi C., Montalti M., Zaccheroni N., Su N., Bradshow J.S., Savage P.B., Izatt R.M., Savage P.B. An Effective Fluorescent Chemosensor for Mercury Ions. II J. Amer. Chem. Soc., 2000. v.122. № 28. 6769−6770
33. Prodi L., Montalti M., Zaccheroni N., Bradshow J.S., Izatt R.M., Savage P.B. Characterization of 5-Chloro-8-Methoxyquinoline appended diaza-18-crown-6 as a chemosensor for cadmium. // Tetranedron. Lett., 2001. v.42. № 16. p.2941−2944
34. Kim S.-H., Han S.-K., Park S.-H., Yoon C.-M., Keum S.-R. Novel fluorescent chemosensor for Li+ based on a squarylium dye carrying a monoazacrown moiety. // Dyes and Pigments, 1999. v.43. № 1. p.21−25
35. Rurack K., Resch-Genger U., Bricks J.L., Spieles M. Cation-triggered 'switching on' of the red/near infrared (NIR) fluorescence of rigid fluoro-phore-spacer-receptor ionophores. // Chem. Commun., 2000. p. 2103−2104
36. Hisafumi H., Tatsuya M., Hiroshi N. Template effects of metal ions on photo-dimerization of bis-l-anthracenecarboxamide linked by the oxyethylene chain. // Tetrahedron Lett., 2002. v.43. № 50. p. 9093−9095
37. Fabbrizzi L., Licchelli M., Pallavicini P. Transition Metals as Switches // Acc. Chem. Res., 1999. v.32. № 10. p. 846−853
38. Amendola V., Fabbrizzi L., Mangano C., Pallavicini P. Molecular Machines Based on Metal Ion Translocation. // Acc. Chem. Res., 2001. v.34. № 6. p. 488−493
39. Fabbrizzi L., Licchelli M., Rospo C., Sacchi D., Zema M. Searching for new fluorescence switches: naphthalene-containing metal complexes whose emission can be controlled by pH variations. // Inorg. Chim. Acta, 2000. v.300−302. p. 453−461
40. Akkaya E.U., Huston M.E., Czarnic A.W. Chelation-Enhanced Fluorescence of Anthrylazamacrocycle Conjugate Probes in Aqueous Solution. // J. Amer. Chem. Soc., 1990. v. l 12. № 9. p.3590−3593
41. Shihadeh Y.A., Benito A., Lloris J. M., Martinez-Manez R., Pardo Т., Soto J.,
42. Marcos M. D. Polyaza and azaoxa macrocyclic receptors functionalised with• 2-f- • • •fluorescent subunits- Hg selective signaling. // J. Chem. Soc., Dalton Trans., 2000. p. 1199−1205
43. Reany O., Gunnlaugsson Т., Parker D. A model system using modulation of lanthanide luminescence to signal Zn in competitive aqueous media. // J. Chem. Soc., Perkin Trans.2, 2000. p.1819−1831
44. Gunnlaugsson Т., Mac Donaila D. A., Parker D. Luminescent molecular logic gates: the two-input inhibit (INH) function. // Chem. Commun., 2000. p. 9394
45. Parker D., Williams J.A.G. Luminescence behavior of cadmium, lead, zinc, copper, nickel and lanthanide complexes of octadentate macrocyclic ligands bearing naphthyl chromophores. // J. Chem. Soc., Perkin Trans.2, 1995. p. 1305−1314
46. Beeby A., Parker D., Williams J.A.G. Photochemical investigation of func-tionalized 1,4,7,10-tetraazacyclododecane ligands incorporating naphthyl chromophores. // J. Chem. Soc., Perkin Trans. 2, 1996. p. 1565−1579
47. Charles S., Yunus S., Dubois F., Vander Donckt E. Determination of cadmium in marine waters: on-line preconcentration and flow-through fluorescence detection. II Anal. Chim. Acta, 2001. v.440. p. 37−43
48. Bernhardt P. V., Flanagan В. M., Riley M. J. Metal-centred versus ligand-centred luminescence quenching of a macrocyclic copper (II) complex. // J. Chem. Soc., Dalton Trans., 1999. p.3579−3584
49. Fabbrizzi L., Licchelli M., Pallavicini P., Parodi L. Controllable Intramolecular Motions That Generate Fluorescent Signals for a Metal Scorpionate Complex. // Angew. Chem. Int. Ed., 1998. v.37. № 6. p. 800−802
50. Ramachandram В., Samanta A. Modulation of metal fluorophore communication to develop structurally simple fluorescent sensors for transition metal ions. // Chem. Commun., 1997, 1037−1038
51. Badugu R. Development of Efficient Fluorosensors for the Transition Metal Ions by Tuning of Photoinduced Intramolecular Electron Transfer (PIET) Communication between the Components. // Chem. Lett., 2002. p. 52−53
52. Huston M.E., Haider K.W., Czarnik A.W. Chelation-Enhanced Fluorescence in 9,10-Bis (TMEDA)anthracene. // J. Amer. Chem. Soc., 1988. v.110. № 13. p. 4460−4462
53. Czarnik A. W. Chemical Communication in Water Using Fluorescent Chemo-sensors. П Acc. Chem. Res., 1994. v.21. № 10. p.302−308
54. Sclafani J.A., Maranto M.T., Sisk T.M., Van Arman S.A. An Aqueous Rati-ometric Fluorescence Probe for Zn (II). // Tetrahedron Lett., 1996. v.37. № 13. p. 2193−2196
55. Fabbrizzi L., Licchelli M., Pallavicini P., Taglietti A. A Zinc (II)-Driven Intramolecular Photoinduced Electron Transfer. // Inorg. Chem., 1996. v.35. № 6. p. 1733−1736
56. Pina F., Bernardo M.A., Garcia-Espana E. Fluorescent Chemosensors Containing Polyamine Receptors. // Eur. J. Inorg. Chem., 2000. p. 2143−2157
57. Alves S., Pina F., Albelda M.T., Garcia-Espana E., Soriano C., Luis S.V. Open-Chain Polyamine Ligands Bearing an Anthracene Unit Chemosensors for Logic Operations at the Molecular Level. // Eur. J. Inorg. Chem., 2001. p.405−412
58. Sancenon F., Descalzo A.B., Lloris J.M., Martinez-Manez R., Pardo Т., Segui M.J., Soto J. Open-chain Polyazaalkanes functionalized with pyrene groups as sensing fluorogenic receptors for metal ions. // Polyhedron, 2002. v.21. p.1397−1404
59. Fabbzizzi L., Licchelli M., Pallavicini P., Perotti A., Taglietti A., Sacehi D. Fluorescent Sensors for Transition Metals Based on Electron-Tranfer and Energy-Transfer Mechanisms. // Chem, Eur. J., 1996. v.2. № 1. p. 75−83
60. Kubo K., Sakurai Т., Mori A. Complexion and fluorescence behavior of 9,10-bisbis (b-hydroxy ethyl) aminomethyl.anthracene. // Talanta, 1999. v.50. p. 73−77
61. Choi M., Kim M., Lee К .D., Han K.-N., Yoon I.-A., Chung H.-J., Yoon J. A New Reverse PET Sensors and Its Chelatoselective Aromatic Cadmiation. // Org. Lett., 2001. v.3. № 22. p.3455−3457
62. Yoon J., Ohler N. H., Vance D. H., Aumiller W. D., Czarnik A. W. A Fluorescent Chemosensor Signaling Only Hg (II) and Cu (II) in Water. // Tetrahedron Lett., 1997. v.38. № 22. p.3845−3848
63. Beltramello M., Gatos M., Mancin F., Tecillab P., Tonellatoa U. A new selective fluorescence chemosensor for Cu (II) in water. // Tetrahedron Lett., 2001. v.42. p.9143−9146
64. Balzani V., Ceroni P., Gestermann S., Kauffmann C., Gorca M., Vogtle F. Dendrimers as fluorescent sensors with signal amplification. // Chem. Com-mun., 2000. p.853−854
65. Lehn J. M. Supramolecular Chemistry. 11 VCN, Weinhei- New York, 1995
66. Kirkovitsi G. J., Shriver J. A., Gale P. A., Sessler J. L. Synthetic Ditopic Receptors. // J. Irtcl. Phenom. Macrocycl. Chem., 2001. v.41. p.69−75
67. Doludda M., Kastenaolth F., Lewitzki E., Grell E. Time-Resolved Response of Fluorescent Alkali Ion Indicators and Detection of Short-Lived Intermediates Upon Binding to Molecular Cavities. // J. Fluor esc., 1996. v. 6. № 3. p.159−164
68. Buet P., Kastenholz F., Grell E., Kab G., Hafner A., Schneider F.M. Trifluorocoumarino Cryptands as Ohotoprotonic Molecules: Basic Features and Theoretical Considerations. H J. Phys. Chem. A., 1999. v.103. № 30. p.5871−5881
69. Ghosh P., Bharadwaj P.K., Roy J., Ghosh S. Transition Metal (II)/(III), Eu (III), and Tb (III) Ions Induced Molecular Photonic OR Gates Using Tri-anthryl Cryptands of Varying Cavity Dimension. // J. Amer. Chem. Soc., 1997. v.119. № 49. p. 11 903−11 909
70. Chae M.-Y., Cherian X.M., Czarnic A.W. New Reagents for the Syntheses of Fluorescent Chemosensors Anthrylogous Ethylene Dibromides. // J. Org. Chem., 1993. v.58. № 21. p. 5797−5801
71. Jang H. O., Nakamura K., Yi S.-S., Kim J. S., Go J. R., Yoon J. Immobilization of Azacrown Ligand onto a Fluorophore. // J. Incl. Phenom. Macrocycl. Chem., 2001. v.40. p. 313−316
72. Iwamoto K., Araki K., Fujishima H., Shinkai S. Fluorogenic Calix4.arene. // J. Chem. Soc., Perkin Trans.1, 1992. p. 1885−1890
73. Jin Т., Ichikawa K., Koyama T. A Fluorescent Calix4. arene as an Intramolecular Eximer Forming Na+ Sensor in Nonaqueous Solution. // J. Chem. Soc., Chem. Commun., 1992. p. 499−450
74. Jin Т. A new Na+ sensor based on intramolecular fluorescence energy transfer derived from calix4.arene. // Chem. Commun., 1999. p. 2491−2492
75. Kubo Y., Obara S., Tokita S. Effective signal control (off-on-off action) by metal ionic inputs on a new chromoionophore-based calix4.crown. // Chem. Commun., 1999. p. 2399−2400
76. H.-F. Ji, R. Dabestani,. G. M. Brown, R. A. Sachleben. A new highly selective calix4. crown-6 fluorescent caesium probe // Chem. Commun., 2000, p. 833−834
77. Ji H.-F., Dabestani R., Brown G.M. A Supramolecular Fluorescent Probe, Activated by Protons To Detect Cesium and Potassium Ions, Mimics the Function of a Logic Gate. II J. Amer. Chem. Soc., 2000. v.122. № 38. p. 93 069 307
78. Kim J.S., Shon O.J., Rim J.A., Kim S.K., Yoon J. Pyrene-Armed Calix4. azacrowns as New Fluorescent Ionophores: «Molecular Taekowndo» Process via Fluorescence Change. // J. Org. Chem., 2002. v.67. № 7. p. 23 482 351
79. Kristian P., Zavodska E., Antos K., Drobnica L. Izotiokyanaty. XIX. Synteza a infracervene spectra polynuklear nuch arylmethylizotiocyanatov. // Che-mickezvesti, 1967. v. 21. № 1−2. p. 57−64.
80. Plater M.J., Greig I., Helfrich M.H., Ralston S.H. The synthesis and evaluation of o-phenylenediamine derivatives as fluorescent probes for nitric oxide detection. // J. Chem. Soc., Perkin Trans. 1, 2001. p. 2553−2559.
81. Пожарский А.Ф., Анисимова В. А., Цупак Е. Б. Практические работы по химии гетероциклов. // Издательство Ростовского Университета- Ростов- на-Дону, 1988.
82. Шепеленко Е.Н. Синтез, строение и превращение стерически напря женных кетоенаминов и кетоенгидразинов. Диссертация на соискание ученой степени кандидата химических наук. Ростов-на-Дону. 2004. 106 с.
83. Гарновский А.Д., Васильченко И. С., Гарновский Д. А. Современные аспекты синтеза металлокомплексов. Основные лиганды и методы. // ЛаПО- Ростов-на-Дону, 2000, 355 с.
84. Княжанский М.И., Метелица А. В. Фотоинициированные процессы в молекулах азометинов и их структурных аналогов. // Издательство Ростовского Университета- Ростов-на-Дону, 1992.
85. Lahlou S., Bitt N., Desvergne J.-P. Syntheses and Photoreactivity of New Bisanthracenes Incorporating One or Two Nitrogen Atoms in the Linkage. // J. Chem. Res. (S), 1998. p.302−303
86. Lin Z., Priyadarshy S., Bartko A., Waldeck D.H. Photophysics and intramolecular excimer formation in a constrained anthracenyl diadduct. // J. Photochem. Photobiol A, Chem., 1997. v.10. p.131−139
87. Bouas-Laurent H., Castellan A., Desvergne J.-P. From Anthracene Photo-dimerization to Jaw Photochromic Materials and Photocrowns. // Pure and Appl. Chem., 1980. v.52. p. 2633−2648
88. Hayashi Т., MatagaN., Sakata Y., Misumi S., Morita M., Tanaka J. Eximer Fluorescence and Photodimerization of Athracenophanes and 1,2-Dianthryl ethanes. // J. Amer. Chem. Soc., 1976. v.98. № 19. p. 5910−5913
89. Foresman J.B., Frisch E. Exploring Chemistry with Electronic Structure Methods.// Gaussian. Inc.- Pittsburgh, 1996.
90. PCMODEL // Selena Software- Bloomigton, 1987.
91. Уэллс А. Структурная неорганическая химия. // Мир- Москва, 1987, т.З. с. 456
92. Reed А.Е., Curtiss Z.A., Weinhold F. Intermolecular interactions from a natural bond orbital, bond-acceptor viewpoint.// Chem. Rev., 7988, v. 88, № 6.p. 899.
93. Торопова В.Ф. Изучение устойчивости тиомочевинных комплексных соединений ртути. //Журн. неорг. химии. 1956. т.1. № 5. с. 930−937
94. Умфлянд Ф., Янсен А., Тириг Д., Вюнш Г. Комплексные соединения в аналитической химии. // Мир- Москва, 1975, 456 с.
95. Яцимирский К.Б., Костромина Н. А., Шека З. А., Давиденко Н. К., Крисс Е. Е., Ермоленко В. И. Химия комплексных соединений редкоземельных элементов. I/ Hayкова Думка- Киев, 1966, 496 с.
96. Henderson W., Nicholson B.K., Rickard C.E.F. Platinum (II) complexes of chelating and monodentate thiourea monocations incorporating chiral, fluorescent or chromophore groups. // Inorg. Chim. Acta, 2001. v.320. p. 101−109
97. Рыбалкин В.П., Дубоносов А. Д., Шепеленко E.H., Попова JI.Л., Брень
98. В.А., Минкин В. И. Фотоинициированная ацилотропная перегруппировка краунсодержащего 2-Ы-ацетил-№(4-амино-15-краун-5)метилен.-3(2Н)-бензо[Ь]тиофена//Журн. орг. химии. 2001. т.37. № 7. с.1083−1085
99. Рыбалкин В.П., Брень В. А., Минкин В. И., Брень Ж. В., Ситкина JI.M. Обратимая термическая и фотоиндуцируемая Zs-Z-изомеризация бен-зоЬ.аннелированных иятичленных гетероциклических аминовинил-кетонов // Журн. орг. химии. 1990. т.26. № 11. е. 2389−2394