Fluorescence sensing of ammonium and organoammonium ions with tripodal oxazoline receptors

Organic Letters

Volumn 5, Issue 9, 2003, Pages 1419-1422

  Ahn, Kyo Han ^a   Ku, Hui Young ^a   Kim, Yusin ^a   Kim, Sung Gon ^a   Kim, Young Kook ^a   Son, Hyung Su ^a   Ku, Ja Kang ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIA; BENZENE; ION; MAGNESIUM; ORGANIC COMPOUND; OXAZOLINE DERIVATIVE; PHENYLGLYCINE; POTASSIUM; RECEPTOR; SODIUM; 2-AMINOPROPANOL; AMINOPROPANOL; CATION; DRUG DERIVATIVE; FLUORESCENT DYE; GLYCINE; OXAZOLE DERIVATIVE; PHENETHYLAMINE DERIVATIVE; PHENYLGLYCINOL; PROPANOLAMINE DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; BINDING AFFINITY; CHIRALITY; DERIVATIZATION; ENANTIOMER; FLUORESCENCE; SENSOR; CHEMISTRY; ELECTRON TRANSPORT; METABOLISM; PHOTOCHEMISTRY; QUANTUM THEORY; SENSITIVITY AND SPECIFICITY; SPECTROFLUOROMETRY; STEREOISOMERISM;

CATIONS; ELECTRON TRANSPORT; FLUORESCENT DYES; GLYCINE; OXAZOLES; PHENETHYLAMINES; PHOTOCHEMISTRY; PROPANOLAMINES; QUANTUM THEORY; QUATERNARY AMMONIUM COMPOUNDS; SENSITIVITY AND SPECIFICITY; SPECTROMETRY, FLUORESCENCE; STEREOISOMERISM;

EID: 0041765004     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034041m     Document Type: Article

References (34)

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11. For the fluorescence sensing of organoammonium ions based on the PET process, see: (a) de Silva, A. P. Angew. Chem., Int. Ed. Engl. 1990, 29, 1173. (b) Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Kotzyba-Hibert, F. ; Lehn, J.-M.; Prodi, L. J. Am. Chem. Soc. 1994, 116, 5741. The fluorescence sensing of chiral organoamines through a quenching mode, not organoammonium ions, based on binaphthol derivatives, see: (d) Pugh, V. J.; Hu, Q.-S.; Pu, L. Angew. Chem., Int. Ed. 2000, 39, 3638. (e) Beer, C.; Rurack, K.; Daub, J. Chem. Commun. 2001, 1138. (f) Reetz, M. T.; Sostmann, S. Tetrahedron 2001, 57, 2515. Lin, J.; Zhang, H.-C.; Pu, L. Org. Lett. 2002, 4, 3297.
12. For the fluorescence sensing of organoammonium ions based on the PET process, see: (a) de Silva, A. P. Angew. Chem., Int. Ed. Engl. 1990, 29, 1173. (b) Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Kotzyba-Hibert, F. ; Lehn, J.-M.; Prodi, L. J. Am. Chem. Soc. 1994, 116, 5741. The fluorescence sensing of chiral organoamines through a quenching mode, not organoammonium ions, based on binaphthol derivatives, see: (d) Pugh, V. J.; Hu, Q.-S.; Pu, L. Angew. Chem., Int. Ed. 2000, 39, 3638. (e) Beer, C.; Rurack, K.; Daub, J. Chem. Commun. 2001, 1138. (f) Reetz, M. T.; Sostmann, S. Tetrahedron 2001, 57, 2515. Lin, J.; Zhang, H.-C.; Pu, L. Org. Lett. 2002, 4, 3297.
13. For the fluorescence sensing of organoammonium ions based on the PET process, see: (a) de Silva, A. P. Angew. Chem., Int. Ed. Engl. 1990, 29, 1173. (b) Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Kotzyba-Hibert, F. ; Lehn, J.-M.; Prodi, L. J. Am. Chem. Soc. 1994, 116, 5741. The fluorescence sensing of chiral organoamines through a quenching mode, not organoammonium ions, based on binaphthol derivatives, see: (d) Pugh, V. J.; Hu, Q.-S.; Pu, L. Angew. Chem., Int. Ed. 2000, 39, 3638. (e) Beer, C.; Rurack, K.; Daub, J. Chem. Commun. 2001, 1138. (f) Reetz, M. T.; Sostmann, S. Tetrahedron 2001, 57, 2515. Lin, J.; Zhang, H.-C.; Pu, L. Org. Lett. 2002, 4, 3297.
14. For the fluorescence sensing of organoammonium ions based on the PET process, see: (a) de Silva, A. P. Angew. Chem., Int. Ed. Engl. 1990, 29, 1173. (b) Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Kotzyba-Hibert, F. ; Lehn, J.-M.; Prodi, L. J. Am. Chem. Soc. 1994, 116, 5741. The fluorescence sensing of chiral organoamines through a quenching mode, not organoammonium ions, based on binaphthol derivatives, see: (d) Pugh, V. J.; Hu, Q.-S.; Pu, L. Angew. Chem., Int. Ed. 2000, 39, 3638. (e) Beer, C.; Rurack, K.; Daub, J. Chem. Commun. 2001, 1138. (f) Reetz, M. T.; Sostmann, S. Tetrahedron 2001, 57, 2515. Lin, J.; Zhang, H.-C.; Pu, L. Org. Lett. 2002, 4, 3297.
15. For the fluorescence sensing of organoammonium ions based on the PET process, see: (a) de Silva, A. P. Angew. Chem., Int. Ed. Engl. 1990, 29, 1173. (b) Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Kotzyba-Hibert, F. ; Lehn, J.-M.; Prodi, L. J. Am. Chem. Soc. 1994, 116, 5741. The fluorescence sensing of chiral organoamines through a quenching mode, not organoammonium ions, based on binaphthol derivatives, see: (d) Pugh, V. J.; Hu, Q.-S.; Pu, L. Angew. Chem., Int. Ed. 2000, 39, 3638. (e) Beer, C.; Rurack, K.; Daub, J. Chem. Commun. 2001, 1138. (f) Reetz, M. T.; Sostmann, S. Tetrahedron 2001, 57, 2515. Lin, J.; Zhang, H.-C.; Pu, L. Org. Lett. 2002, 4, 3297.
16. For chemosensors that utilize the binding-induced conformational restriction of fluorophores, see: (a) Sandanayake, K.; Nakashima, H.; Shinkai, S. Chem. Commun. 1994, 1621. (b) Takeuchi, M.; Mizuno, T.; Shinmori, H.; Nakashima, M.; Shinkai, S. Tetrahedron, 1996, 52, 1195. (c) Black, C. B.; Andrioletti, B.; Try, A. C.; Ruiperez, C.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 10438. (d) McFarland, S. A.; Finney, N. S. J. Am. Chem. Soc. 2001, 123, 1260. (e) McFarland, S. A.; Finney, N. S. J. Am. Chem. Soc. 2002, 124, 1178.
17. For chemosensors that utilize the binding-induced conformational restriction of fluorophores, see: (a) Sandanayake, K.; Nakashima, H.; Shinkai, S. Chem. Commun. 1994, 1621. (b) Takeuchi, M.; Mizuno, T.; Shinmori, H.; Nakashima, M.; Shinkai, S. Tetrahedron, 1996, 52, 1195. (c) Black, C. B.; Andrioletti, B.; Try, A. C.; Ruiperez, C.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 10438. (d) McFarland, S. A.; Finney, N. S. J. Am. Chem. Soc. 2001, 123, 1260. (e) McFarland, S. A.; Finney, N. S. J. Am. Chem. Soc. 2002, 124, 1178.
18. For chemosensors that utilize the binding-induced conformational restriction of fluorophores, see: (a) Sandanayake, K.; Nakashima, H.; Shinkai, S. Chem. Commun. 1994, 1621. (b) Takeuchi, M.; Mizuno, T.; Shinmori, H.; Nakashima, M.; Shinkai, S. Tetrahedron, 1996, 52, 1195. (c) Black, C. B.; Andrioletti, B.; Try, A. C.; Ruiperez, C.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 10438. (d) McFarland, S. A.; Finney, N. S. J. Am. Chem. Soc. 2001, 123, 1260. (e) McFarland, S. A.; Finney, N. S. J. Am. Chem. Soc. 2002, 124, 1178.
19. For chemosensors that utilize the binding-induced conformational restriction of fluorophores, see: (a) Sandanayake, K.; Nakashima, H.; Shinkai, S. Chem. Commun. 1994, 1621. (b) Takeuchi, M.; Mizuno, T.; Shinmori, H.; Nakashima, M.; Shinkai, S. Tetrahedron, 1996, 52, 1195. (c) Black, C. B.; Andrioletti, B.; Try, A. C.; Ruiperez, C.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 10438. (d) McFarland, S. A.; Finney, N. S. J. Am. Chem. Soc. 2001, 123, 1260. (e) McFarland, S. A.; Finney, N. S. J. Am. Chem. Soc. 2002, 124, 1178.
20. For chemosensors that utilize the binding-induced conformational restriction of fluorophores, see: (a) Sandanayake, K.; Nakashima, H.; Shinkai, S. Chem. Commun. 1994, 1621. (b) Takeuchi, M.; Mizuno, T.; Shinmori, H.; Nakashima, M.; Shinkai, S. Tetrahedron, 1996, 52, 1195. (c) Black, C. B.; Andrioletti, B.; Try, A. C.; Ruiperez, C.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 10438. (d) McFarland, S. A.; Finney, N. S. J. Am. Chem. Soc. 2001, 123, 1260. (e) McFarland, S. A.; Finney, N. S. J. Am. Chem. Soc. 2002, 124, 1178.
21. 3 symmetric, benzene-based tripodal receptors, see: (a) Metzger, A.; Lynch, V. M. ; Anslyn, E. V. Angew. Chem., Int. Ed. Engl. 1997, 36, 862. (b) Niikura, K.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc. 1998, 120, 8533. (c) Sato, K.; Arai, S.; Yamagishi, T. Tetrahedron Lett. 1999, 40, 5219. (d) Chin, J.; Walsdorff, C.; Stranix, B.; Oh, J.; Chung, H. J.; Park, S.-M.; Kim, K. Angew. Chem., Int Ed. 1999, 38, 2756. (e) Lavigne, J. L.; Anslyn, E. V. Angew. Chem., Int. Ed. 1999, 38, 3666. (f) Kim, H.-J.; Kim, Y.-H.; Hong, J.-I. Tetrahedron Lett. 2001, 42, 5049.
22. 3 symmetric, benzene-based tripodal receptors, see: (a) Metzger, A.; Lynch, V. M. ; Anslyn, E. V. Angew. Chem., Int. Ed. Engl. 1997, 36, 862. (b) Niikura, K.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc. 1998, 120, 8533. (c) Sato, K.; Arai, S.; Yamagishi, T. Tetrahedron Lett. 1999, 40, 5219. (d) Chin, J.; Walsdorff, C.; Stranix, B.; Oh, J.; Chung, H. J.; Park, S.-M.; Kim, K. Angew. Chem., Int Ed. 1999, 38, 2756. (e) Lavigne, J. L.; Anslyn, E. V. Angew. Chem., Int. Ed. 1999, 38, 3666. (f) Kim, H.-J.; Kim, Y.-H.; Hong, J.-I. Tetrahedron Lett. 2001, 42, 5049.
23. 3 symmetric, benzene-based tripodal receptors, see: (a) Metzger, A.; Lynch, V. M. ; Anslyn, E. V. Angew. Chem., Int. Ed. Engl. 1997, 36, 862. (b) Niikura, K.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc. 1998, 120, 8533. (c) Sato, K.; Arai, S.; Yamagishi, T. Tetrahedron Lett. 1999, 40, 5219. (d) Chin, J.; Walsdorff, C.; Stranix, B.; Oh, J.; Chung, H. J.; Park, S.-M.; Kim, K. Angew. Chem., Int Ed. 1999, 38, 2756. (e) Lavigne, J. L.; Anslyn, E. V. Angew. Chem., Int. Ed. 1999, 38, 3666. (f) Kim, H.-J.; Kim, Y.-H.; Hong, J.-I. Tetrahedron Lett. 2001, 42, 5049.
24. 3 symmetric, benzene-based tripodal receptors, see: (a) Metzger, A.; Lynch, V. M. ; Anslyn, E. V. Angew. Chem., Int. Ed. Engl. 1997, 36, 862. (b) Niikura, K.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc. 1998, 120, 8533. (c) Sato, K.; Arai, S.; Yamagishi, T. Tetrahedron Lett. 1999, 40, 5219. (d) Chin, J.; Walsdorff, C.; Stranix, B.; Oh, J.; Chung, H. J.; Park, S.-M.; Kim, K. Angew. Chem., Int Ed. 1999, 38, 2756. (e) Lavigne, J. L.; Anslyn, E. V. Angew. Chem., Int. Ed. 1999, 38, 3666. (f) Kim, H.-J.; Kim, Y.-H.; Hong, J.-I. Tetrahedron Lett. 2001, 42, 5049.
25. 3 symmetric, benzene-based tripodal receptors, see: (a) Metzger, A.; Lynch, V. M. ; Anslyn, E. V. Angew. Chem., Int. Ed. Engl. 1997, 36, 862. (b) Niikura, K.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc. 1998, 120, 8533. (c) Sato, K.; Arai, S.; Yamagishi, T. Tetrahedron Lett. 1999, 40, 5219. (d) Chin, J.; Walsdorff, C.; Stranix, B.; Oh, J.; Chung, H. J.; Park, S.-M.; Kim, K. Angew. Chem., Int Ed. 1999, 38, 2756. (e) Lavigne, J. L.; Anslyn, E. V. Angew. Chem., Int. Ed. 1999, 38, 3666. (f) Kim, H.-J.; Kim, Y.-H.; Hong, J.-I. Tetrahedron Lett. 2001, 42, 5049.
26. 3 symmetric, benzene-based tripodal receptors, see: (a) Metzger, A.; Lynch, V. M. ; Anslyn, E. V. Angew. Chem., Int. Ed. Engl. 1997, 36, 862. (b) Niikura, K.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc. 1998, 120, 8533. (c) Sato, K.; Arai, S.; Yamagishi, T. Tetrahedron Lett. 1999, 40, 5219. (d) Chin, J.; Walsdorff, C.; Stranix, B.; Oh, J.; Chung, H. J.; Park, S.-M.; Kim, K. Angew. Chem., Int Ed. 1999, 38, 2756. (e) Lavigne, J. L.; Anslyn, E. V. Angew. Chem., Int. Ed. 1999, 38, 3666. (f) Kim, H.-J.; Kim, Y.-H.; Hong, J.-I. Tetrahedron Lett. 2001, 42, 5049.
27. This problem may be solved, for example, by introducing conjugation moieties such as arylvinyl groups to the benzene ring instead of the 2,4,6-trimethyl groups, which is underway.
28. 2a,c followed by fluorescence analysis may be used.
29. Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 2nd ed., Kluwer Academic: New York, 1999.
30. + 748.3539, found 748.3527.
31. Takacs, J. M.; Jaber, M. R.; Vellekoop, A. S. J. Org. Chem. 1998, 63, 2742.
32. 2H was added. The result suggests that the protonation of the oxazoline nitrogen perturbs the fluorescence of 1a. A further study is necessary to address the quenching mechanism.
33. Nijegorodov, N. I.; Downey, W. S. J. Phys. Chem. 1994, 98, 5639 and references therein.
34. -1, respectively, determined for the picrate salts by the extraction-UV titration method (ref 2a).