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Volumn 127, Issue 10, 2005, Pages 3373-3379

A molecular flytrap for the selective binding of citrate and other tricarboxylates in water

Author keywords

[No Author keywords available]

Indexed keywords

ASSOCIATION REACTIONS; CARBOXYLIC ACIDS; FLUORESCENCE; POLYPYRROLES; SALTS; SOLVENTS; SYNTHESIS (CHEMICAL); ULTRAVIOLET SPECTROSCOPY; WATER;

EID: 14944376608     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0433469     Document Type: Article
Times cited : (157)

References (84)
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    • Recent examples: (a) Nguyen, B. T.; Wiskur, S. L.; Anslyn, E. V. Org. Lett. 2004, 6, 2499-2501. (b) Piatek, A. M.; Bomble, Y. J.; Wiskur, S. L.; Anslyn, E. V. J. Am. Chem. Soc. 2004, 126, 6072-6077. (c) Hu, L.; Anslyn, E. V. J. Am. Chem. Soc. 2004, 126, 3676-3677. (d) Buryak, A.; Severin, K. Angew. Chem, Int. Ed. 2004, 43, 4771-4774. (e) Tobey, S. L.; Anslyn, E. V. Org. Lett. 2003, 5, 2029-2031.
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    • Buryak, A.1    Severin, K.2
  • 12
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    • Recent examples: (a) Nguyen, B. T.; Wiskur, S. L.; Anslyn, E. V. Org. Lett. 2004, 6, 2499-2501. (b) Piatek, A. M.; Bomble, Y. J.; Wiskur, S. L.; Anslyn, E. V. J. Am. Chem. Soc. 2004, 126, 6072-6077. (c) Hu, L.; Anslyn, E. V. J. Am. Chem. Soc. 2004, 126, 3676-3677. (d) Buryak, A.; Severin, K. Angew. Chem, Int. Ed. 2004, 43, 4771-4774. (e) Tobey, S. L.; Anslyn, E. V. Org. Lett. 2003, 5, 2029-2031.
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    • Selected recent examples of supramolecular aggregates that are stable in water: (a) Molt, O.; Rübeling, R.; Schäfer, G.; Schrader, T. Chem. - Eur. J. 2004, 10, 4225-4232. (b) Wiskur, S. L.; Lavigne, J. J.; Metzger, A.; Tobey, S. L.; Lynch, V.; Anslyn, E. V. Chem. - Eur. J. 2004, 10, 3792-3804. (c) Schmuck, C.; Wienand, W. J. Am. Chem. Soc. 2003, 125, 452-459. (d) Corbellini, F.; Di Costanzo, L.; Crego-Calama, M.; Geremia, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2003, 125, 9946-9947. (e) Rekharsky, M.; Inoue, Y.; Tobey, S.; Metzger, A.; Anslyn, E. J. Am. Chem. Soc. 2002, 124, 14959-14967. (f) Grawe, T.; Schrader, T.; Zadmard, R.; Kraft, A. J. Org. Chem. 2002, 67, 3755-3763. (g) Fiammengo, R.; Timmerman, P.; De Jong, F.; Reinhoudt, D. N. Chem. Commun. 2000, 2313-2314. (h) Hamilin, B.; Jullien, L.; Derouet, C.; Hervé du Penhoat, C.; Berthault, P. J. Am. Chem. Soc. 1998, 120, 8438-8447. (i) Bok Lee, S.; Hong, J.-I. Tetrahedron Lett. 1996, 37, 8501-8504.
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    • Molt, O.1    Rübeling, R.2    Schäfer, G.3    Schrader, T.4
  • 14
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    • Selected recent examples of supramolecular aggregates that are stable in water: (a) Molt, O.; Rübeling, R.; Schäfer, G.; Schrader, T. Chem. - Eur. J. 2004, 10, 4225-4232. (b) Wiskur, S. L.; Lavigne, J. J.; Metzger, A.; Tobey, S. L.; Lynch, V.; Anslyn, E. V. Chem. - Eur. J. 2004, 10, 3792-3804. (c) Schmuck, C.; Wienand, W. J. Am. Chem. Soc. 2003, 125, 452-459. (d) Corbellini, F.; Di Costanzo, L.; Crego-Calama, M.; Geremia, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2003, 125, 9946-9947. (e) Rekharsky, M.; Inoue, Y.; Tobey, S.; Metzger, A.; Anslyn, E. J. Am. Chem. Soc. 2002, 124, 14959-14967. (f) Grawe, T.; Schrader, T.; Zadmard, R.; Kraft, A. J. Org. Chem. 2002, 67, 3755-3763. (g) Fiammengo, R.; Timmerman, P.; De Jong, F.; Reinhoudt, D. N. Chem. Commun. 2000, 2313-2314. (h) Hamilin, B.; Jullien, L.; Derouet, C.; Hervé du Penhoat, C.; Berthault, P. J. Am. Chem. Soc. 1998, 120, 8438-8447. (i) Bok Lee, S.; Hong, J.-I. Tetrahedron Lett. 1996, 37, 8501-8504.
    • (2004) Chem. - Eur. J. , vol.10 , pp. 3792-3804
    • Wiskur, S.L.1    Lavigne, J.J.2    Metzger, A.3    Tobey, S.L.4    Lynch, V.5    Anslyn, E.V.6
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    • Selected recent examples of supramolecular aggregates that are stable in water: (a) Molt, O.; Rübeling, R.; Schäfer, G.; Schrader, T. Chem. - Eur. J. 2004, 10, 4225-4232. (b) Wiskur, S. L.; Lavigne, J. J.; Metzger, A.; Tobey, S. L.; Lynch, V.; Anslyn, E. V. Chem. - Eur. J. 2004, 10, 3792-3804. (c) Schmuck, C.; Wienand, W. J. Am. Chem. Soc. 2003, 125, 452-459. (d) Corbellini, F.; Di Costanzo, L.; Crego-Calama, M.; Geremia, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2003, 125, 9946-9947. (e) Rekharsky, M.; Inoue, Y.; Tobey, S.; Metzger, A.; Anslyn, E. J. Am. Chem. Soc. 2002, 124, 14959-14967. (f) Grawe, T.; Schrader, T.; Zadmard, R.; Kraft, A. J. Org. Chem. 2002, 67, 3755-3763. (g) Fiammengo, R.; Timmerman, P.; De Jong, F.; Reinhoudt, D. N. Chem. Commun. 2000, 2313-2314. (h) Hamilin, B.; Jullien, L.; Derouet, C.; Hervé du Penhoat, C.; Berthault, P. J. Am. Chem. Soc. 1998, 120, 8438-8447. (i) Bok Lee, S.; Hong, J.-I. Tetrahedron Lett. 1996, 37, 8501-8504.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 452-459
    • Schmuck, C.1    Wienand, W.2
  • 16
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    • Selected recent examples of supramolecular aggregates that are stable in water: (a) Molt, O.; Rübeling, R.; Schäfer, G.; Schrader, T. Chem. - Eur. J. 2004, 10, 4225-4232. (b) Wiskur, S. L.; Lavigne, J. J.; Metzger, A.; Tobey, S. L.; Lynch, V.; Anslyn, E. V. Chem. - Eur. J. 2004, 10, 3792-3804. (c) Schmuck, C.; Wienand, W. J. Am. Chem. Soc. 2003, 125, 452-459. (d) Corbellini, F.; Di Costanzo, L.; Crego-Calama, M.; Geremia, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2003, 125, 9946-9947. (e) Rekharsky, M.; Inoue, Y.; Tobey, S.; Metzger, A.; Anslyn, E. J. Am. Chem. Soc. 2002, 124, 14959-14967. (f) Grawe, T.; Schrader, T.; Zadmard, R.; Kraft, A. J. Org. Chem. 2002, 67, 3755-3763. (g) Fiammengo, R.; Timmerman, P.; De Jong, F.; Reinhoudt, D. N. Chem. Commun. 2000, 2313-2314. (h) Hamilin, B.; Jullien, L.; Derouet, C.; Hervé du Penhoat, C.; Berthault, P. J. Am. Chem. Soc. 1998, 120, 8438-8447. (i) Bok Lee, S.; Hong, J.-I. Tetrahedron Lett. 1996, 37, 8501-8504.
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    • Corbellini, F.1    Di Costanzo, L.2    Crego-Calama, M.3    Geremia, S.4    Reinhoudt, D.N.5
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    • Selected recent examples of supramolecular aggregates that are stable in water: (a) Molt, O.; Rübeling, R.; Schäfer, G.; Schrader, T. Chem. - Eur. J. 2004, 10, 4225-4232. (b) Wiskur, S. L.; Lavigne, J. J.; Metzger, A.; Tobey, S. L.; Lynch, V.; Anslyn, E. V. Chem. - Eur. J. 2004, 10, 3792-3804. (c) Schmuck, C.; Wienand, W. J. Am. Chem. Soc. 2003, 125, 452-459. (d) Corbellini, F.; Di Costanzo, L.; Crego-Calama, M.; Geremia, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2003, 125, 9946-9947. (e) Rekharsky, M.; Inoue, Y.; Tobey, S.; Metzger, A.; Anslyn, E. J. Am. Chem. Soc. 2002, 124, 14959-14967. (f) Grawe, T.; Schrader, T.; Zadmard, R.; Kraft, A. J. Org. Chem. 2002, 67, 3755-3763. (g) Fiammengo, R.; Timmerman, P.; De Jong, F.; Reinhoudt, D. N. Chem. Commun. 2000, 2313-2314. (h) Hamilin, B.; Jullien, L.; Derouet, C.; Hervé du Penhoat, C.; Berthault, P. J. Am. Chem. Soc. 1998, 120, 8438-8447. (i) Bok Lee, S.; Hong, J.-I. Tetrahedron Lett. 1996, 37, 8501-8504.
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    • Rekharsky, M.1    Inoue, Y.2    Tobey, S.3    Metzger, A.4    Anslyn, E.5
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    • Selected recent examples of supramolecular aggregates that are stable in water: (a) Molt, O.; Rübeling, R.; Schäfer, G.; Schrader, T. Chem. - Eur. J. 2004, 10, 4225-4232. (b) Wiskur, S. L.; Lavigne, J. J.; Metzger, A.; Tobey, S. L.; Lynch, V.; Anslyn, E. V. Chem. - Eur. J. 2004, 10, 3792-3804. (c) Schmuck, C.; Wienand, W. J. Am. Chem. Soc. 2003, 125, 452-459. (d) Corbellini, F.; Di Costanzo, L.; Crego-Calama, M.; Geremia, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2003, 125, 9946-9947. (e) Rekharsky, M.; Inoue, Y.; Tobey, S.; Metzger, A.; Anslyn, E. J. Am. Chem. Soc. 2002, 124, 14959-14967. (f) Grawe, T.; Schrader, T.; Zadmard, R.; Kraft, A. J. Org. Chem. 2002, 67, 3755-3763. (g) Fiammengo, R.; Timmerman, P.; De Jong, F.; Reinhoudt, D. N. Chem. Commun. 2000, 2313-2314. (h) Hamilin, B.; Jullien, L.; Derouet, C.; Hervé du Penhoat, C.; Berthault, P. J. Am. Chem. Soc. 1998, 120, 8438-8447. (i) Bok Lee, S.; Hong, J.-I. Tetrahedron Lett. 1996, 37, 8501-8504.
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    • Grawe, T.1    Schrader, T.2    Zadmard, R.3    Kraft, A.4
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    • Selected recent examples of supramolecular aggregates that are stable in water: (a) Molt, O.; Rübeling, R.; Schäfer, G.; Schrader, T. Chem. - Eur. J. 2004, 10, 4225-4232. (b) Wiskur, S. L.; Lavigne, J. J.; Metzger, A.; Tobey, S. L.; Lynch, V.; Anslyn, E. V. Chem. - Eur. J. 2004, 10, 3792-3804. (c) Schmuck, C.; Wienand, W. J. Am. Chem. Soc. 2003, 125, 452-459. (d) Corbellini, F.; Di Costanzo, L.; Crego-Calama, M.; Geremia, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2003, 125, 9946-9947. (e) Rekharsky, M.; Inoue, Y.; Tobey, S.; Metzger, A.; Anslyn, E. J. Am. Chem. Soc. 2002, 124, 14959-14967. (f) Grawe, T.; Schrader, T.; Zadmard, R.; Kraft, A. J. Org. Chem. 2002, 67, 3755-3763. (g) Fiammengo, R.; Timmerman, P.; De Jong, F.; Reinhoudt, D. N. Chem. Commun. 2000, 2313-2314. (h) Hamilin, B.; Jullien, L.; Derouet, C.; Hervé du Penhoat, C.; Berthault, P. J. Am. Chem. Soc. 1998, 120, 8438-8447. (i) Bok Lee, S.; Hong, J.-I. Tetrahedron Lett. 1996, 37, 8501-8504.
    • (2000) Chem. Commun. , pp. 2313-2314
    • Fiammengo, R.1    Timmerman, P.2    De Jong, F.3    Reinhoudt, D.N.4
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    • Selected recent examples of supramolecular aggregates that are stable in water: (a) Molt, O.; Rübeling, R.; Schäfer, G.; Schrader, T. Chem. - Eur. J. 2004, 10, 4225-4232. (b) Wiskur, S. L.; Lavigne, J. J.; Metzger, A.; Tobey, S. L.; Lynch, V.; Anslyn, E. V. Chem. - Eur. J. 2004, 10, 3792-3804. (c) Schmuck, C.; Wienand, W. J. Am. Chem. Soc. 2003, 125, 452-459. (d) Corbellini, F.; Di Costanzo, L.; Crego-Calama, M.; Geremia, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2003, 125, 9946-9947. (e) Rekharsky, M.; Inoue, Y.; Tobey, S.; Metzger, A.; Anslyn, E. J. Am. Chem. Soc. 2002, 124, 14959-14967. (f) Grawe, T.; Schrader, T.; Zadmard, R.; Kraft, A. J. Org. Chem. 2002, 67, 3755-3763. (g) Fiammengo, R.; Timmerman, P.; De Jong, F.; Reinhoudt, D. N. Chem. Commun. 2000, 2313-2314. (h) Hamilin, B.; Jullien, L.; Derouet, C.; Hervé du Penhoat, C.; Berthault, P. J. Am. Chem. Soc. 1998, 120, 8438-8447. (i) Bok Lee, S.; Hong, J.-I. Tetrahedron Lett. 1996, 37, 8501-8504.
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    • Hamilin, B.1    Jullien, L.2    Derouet, C.3    Hervé Du Penhoat, C.4    Berthault, P.5
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    • Selected recent examples of supramolecular aggregates that are stable in water: (a) Molt, O.; Rübeling, R.; Schäfer, G.; Schrader, T. Chem. - Eur. J. 2004, 10, 4225-4232. (b) Wiskur, S. L.; Lavigne, J. J.; Metzger, A.; Tobey, S. L.; Lynch, V.; Anslyn, E. V. Chem. - Eur. J. 2004, 10, 3792-3804. (c) Schmuck, C.; Wienand, W. J. Am. Chem. Soc. 2003, 125, 452-459. (d) Corbellini, F.; Di Costanzo, L.; Crego-Calama, M.; Geremia, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2003, 125, 9946-9947. (e) Rekharsky, M.; Inoue, Y.; Tobey, S.; Metzger, A.; Anslyn, E. J. Am. Chem. Soc. 2002, 124, 14959-14967. (f) Grawe, T.; Schrader, T.; Zadmard, R.; Kraft, A. J. Org. Chem. 2002, 67, 3755-3763. (g) Fiammengo, R.; Timmerman, P.; De Jong, F.; Reinhoudt, D. N. Chem. Commun. 2000, 2313-2314. (h) Hamilin, B.; Jullien, L.; Derouet, C.; Hervé du Penhoat, C.; Berthault, P. J. Am. Chem. Soc. 1998, 120, 8438-8447. (i) Bok Lee, S.; Hong, J.-I. Tetrahedron Lett. 1996, 37, 8501-8504.
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