Supramolecular dendrimer chemistry: Using dendritic crown ethers to reversibly generate functional assemblies

Tetrahedron

Volumn 59, Issue 22, 2003, Pages 3999-4009

  Dykes, Graham M ^a   Smith, David K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Crown ethers; Dendrimers; Gels; Self assembly; Supramolecular chemistry

Indexed keywords

AMMONIA; CROWN ETHER DERIVATIVE; LYSINE; POTASSIUM ION; SOLVENT;

ARTICLE; BINDING AFFINITY; BINDING ASSAY; COMPLEX FORMATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTEIN INTERACTION; STOICHIOMETRY; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

GOES;

EID: 0038634870     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00468-X     Document Type: Article

References (107)

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2. General references describing dendrimer chemistry include: (a) Newkome G.R., Moorefield C.N., Vögtle F. Dendrimers and Dendrons, Concepts, Syntheses, Applications. 2001;VCH, Weinheim, (b) Chow H.-F., Mong T.K.-K., Nongrum M.F., Wan C.-W. Tetrahedron. 54:1998;8543-8660 (c) Matthews O.A., Shipway A.N., Stoddart J.F. Prog. Polym. Sci. 23:1998;1-56 (d) Fischer M., Vögtle F. Angew. Chem. Int. Ed. 38:1999;884-905 (e) Grayson S.M., Fréchet J.M.J. Chem. Rev. 101:2001;3819-3867 (f) Dykes G.M. J. Chem. Technol. Biotechnol. 76:2001;903-918.
3. General references describing dendrimer chemistry include: (a) Newkome G.R., Moorefield C.N., Vögtle F. Dendrimers and Dendrons, Concepts, Syntheses, Applications. 2001;VCH, Weinheim, (b) Chow H.-F., Mong T.K.-K., Nongrum M.F., Wan C.-W. Tetrahedron. 54:1998;8543-8660 (c) Matthews O.A., Shipway A.N., Stoddart J.F. Prog. Polym. Sci. 23:1998;1-56 (d) Fischer M., Vögtle F. Angew. Chem. Int. Ed. 38:1999;884-905 (e) Grayson S.M., Fréchet J.M.J. Chem. Rev. 101:2001;3819-3867 (f) Dykes G.M. J. Chem. Technol. Biotechnol. 76:2001;903-918.
4. General references describing dendrimer chemistry include: (a) Newkome G.R., Moorefield C.N., Vögtle F. Dendrimers and Dendrons, Concepts, Syntheses, Applications. 2001;VCH, Weinheim, (b) Chow H.-F., Mong T.K.-K., Nongrum M.F., Wan C.-W. Tetrahedron. 54:1998;8543-8660 (c) Matthews O.A., Shipway A.N., Stoddart J.F. Prog. Polym. Sci. 23:1998;1-56 (d) Fischer M., Vögtle F. Angew. Chem. Int. Ed. 38:1999;884-905 (e) Grayson S.M., Fréchet J.M.J. Chem. Rev. 101:2001;3819-3867 (f) Dykes G.M. J. Chem. Technol. Biotechnol. 76:2001;903-918.
5. General references describing dendrimer chemistry include: (a) Newkome G.R., Moorefield C.N., Vögtle F. Dendrimers and Dendrons, Concepts, Syntheses, Applications. 2001;VCH, Weinheim, (b) Chow H.-F., Mong T.K.-K., Nongrum M.F., Wan C.-W. Tetrahedron. 54:1998;8543-8660 (c) Matthews O.A., Shipway A.N., Stoddart J.F. Prog. Polym. Sci. 23:1998;1-56 (d) Fischer M., Vögtle F. Angew. Chem. Int. Ed. 38:1999;884-905 (e) Grayson S.M., Fréchet J.M.J. Chem. Rev. 101:2001;3819-3867 (f) Dykes G.M. J. Chem. Technol. Biotechnol. 76:2001;903-918.
6. General references describing dendrimer chemistry include: (a) Newkome G.R., Moorefield C.N., Vögtle F. Dendrimers and Dendrons, Concepts, Syntheses, Applications. 2001;VCH, Weinheim, (b) Chow H.-F., Mong T.K.-K., Nongrum M.F., Wan C.-W. Tetrahedron. 54:1998;8543-8660 (c) Matthews O.A., Shipway A.N., Stoddart J.F. Prog. Polym. Sci. 23:1998;1-56 (d) Fischer M., Vögtle F. Angew. Chem. Int. Ed. 38:1999;884-905 (e) Grayson S.M., Fréchet J.M.J. Chem. Rev. 101:2001;3819-3867 (f) Dykes G.M. J. Chem. Technol. Biotechnol. 76:2001;903-918.
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47. For selected examples see: (a) Percec V., Ahn C.-H., Ungar G., Yeardley D.J.P., Möller M., Sheiko S.S. Nature. 391:1998;161-164 (b) Percec V., Cho W.-D., Mosier P.E., Ungar G., Yeardley D.J.P. J. Am. Chem. Soc. 120:1998;11061-11070 (c) Percec V., Cho W.D., Ungar G. J. Am. Chem. Soc. 122:2000;10273-10281 (d) Percec V., Cho W.D., Ungar G., Yeardley D.J.P. J. Am. Chem. Soc. 123:2002;1302-1315 (e) Schenning A.P.H.J., Jonkheijm P., Hofkens J., De Feyter S., Asavei T., Cotlet M., De Schryver F.C., Meijer E.W. Chem. Commun. 2002;1264-1265 (f) Liu D.J., Zhang H., Grim P.C.M., De Feyter S., Wiesler U.M., Berresheim A.J., Müllen K., De Schryver F.C. Langmuir. 18:2002;2385-2391 (g) Lee M., Jeong Y.S., Cho B.K., Oh N.K., Zin W.C. Chem. Eur. J. 8:2002;876-883 (h) Dardel B., Guillon D., Heinrich B., Deschenaux R. J. Mater. Chem. 11:2001;2814-2831 (i) Marcos M., Gimenez R., Serrano J.L., Donnio B., Heinrich B., Guillon D. Chem. Eur. J. 7:2001;1006-1013.
48. For selected examples see: (a) Percec V., Ahn C.-H., Ungar G., Yeardley D.J.P., Möller M., Sheiko S.S. Nature. 391:1998;161-164 (b) Percec V., Cho W.-D., Mosier P.E., Ungar G., Yeardley D.J.P. J. Am. Chem. Soc. 120:1998;11061-11070 (c) Percec V., Cho W.D., Ungar G. J. Am. Chem. Soc. 122:2000;10273-10281 (d) Percec V., Cho W.D., Ungar G., Yeardley D.J.P. J. Am. Chem. Soc. 123:2002;1302-1315 (e) Schenning A.P.H.J., Jonkheijm P., Hofkens J., De Feyter S., Asavei T., Cotlet M., De Schryver F.C., Meijer E.W. Chem. Commun. 2002;1264-1265 (f) Liu D.J., Zhang H., Grim P.C.M., De Feyter S., Wiesler U.M., Berresheim A.J., Müllen K., De Schryver F.C. Langmuir. 18:2002;2385-2391 (g) Lee M., Jeong Y.S., Cho B.K., Oh N.K., Zin W.C. Chem. Eur. J. 8:2002;876-883 (h) Dardel B., Guillon D., Heinrich B., Deschenaux R. J. Mater. Chem. 11:2001;2814-2831 (i) Marcos M., Gimenez R., Serrano J.L., Donnio B., Heinrich B., Guillon D. Chem. Eur. J. 7:2001;1006-1013.
49. For selected examples see: (a) Percec V., Ahn C.-H., Ungar G., Yeardley D.J.P., Möller M., Sheiko S.S. Nature. 391:1998;161-164 (b) Percec V., Cho W.-D., Mosier P.E., Ungar G., Yeardley D.J.P. J. Am. Chem. Soc. 120:1998;11061-11070 (c) Percec V., Cho W.D., Ungar G. J. Am. Chem. Soc. 122:2000;10273-10281 (d) Percec V., Cho W.D., Ungar G., Yeardley D.J.P. J. Am. Chem. Soc. 123:2002;1302-1315 (e) Schenning A.P.H.J., Jonkheijm P., Hofkens J., De Feyter S., Asavei T., Cotlet M., De Schryver F.C., Meijer E.W. Chem. Commun. 2002;1264-1265 (f) Liu D.J., Zhang H., Grim P.C.M., De Feyter S., Wiesler U.M., Berresheim A.J., Müllen K., De Schryver F.C. Langmuir. 18:2002;2385-2391 (g) Lee M., Jeong Y.S., Cho B.K., Oh N.K., Zin W.C. Chem. Eur. J. 8:2002;876-883 (h) Dardel B., Guillon D., Heinrich B., Deschenaux R. J. Mater. Chem. 11:2001;2814-2831 (i) Marcos M., Gimenez R., Serrano J.L., Donnio B., Heinrich B., Guillon D. Chem. Eur. J. 7:2001;1006-1013.
50. For selected examples see: (a) Percec V., Ahn C.-H., Ungar G., Yeardley D.J.P., Möller M., Sheiko S.S. Nature. 391:1998;161-164 (b) Percec V., Cho W.-D., Mosier P.E., Ungar G., Yeardley D.J.P. J. Am. Chem. Soc. 120:1998;11061-11070 (c) Percec V., Cho W.D., Ungar G. J. Am. Chem. Soc. 122:2000;10273-10281 (d) Percec V., Cho W.D., Ungar G., Yeardley D.J.P. J. Am. Chem. Soc. 123:2002;1302-1315 (e) Schenning A.P.H.J., Jonkheijm P., Hofkens J., De Feyter S., Asavei T., Cotlet M., De Schryver F.C., Meijer E.W. Chem. Commun. 2002;1264-1265 (f) Liu D.J., Zhang H., Grim P.C.M., De Feyter S., Wiesler U.M., Berresheim A.J., Müllen K., De Schryver F.C. Langmuir. 18:2002;2385-2391 (g) Lee M., Jeong Y.S., Cho B.K., Oh N.K., Zin W.C. Chem. Eur. J. 8:2002;876-883 (h) Dardel B., Guillon D., Heinrich B., Deschenaux R. J. Mater. Chem. 11:2001;2814-2831 (i) Marcos M., Gimenez R., Serrano J.L., Donnio B., Heinrich B., Guillon D. Chem. Eur. J. 7:2001;1006-1013.
51. For selected examples see: (a) Percec V., Ahn C.-H., Ungar G., Yeardley D.J.P., Möller M., Sheiko S.S. Nature. 391:1998;161-164 (b) Percec V., Cho W.-D., Mosier P.E., Ungar G., Yeardley D.J.P. J. Am. Chem. Soc. 120:1998;11061-11070 (c) Percec V., Cho W.D., Ungar G. J. Am. Chem. Soc. 122:2000;10273-10281 (d) Percec V., Cho W.D., Ungar G., Yeardley D.J.P. J. Am. Chem. Soc. 123:2002;1302-1315 (e) Schenning A.P.H.J., Jonkheijm P., Hofkens J., De Feyter S., Asavei T., Cotlet M., De Schryver F.C., Meijer E.W. Chem. Commun. 2002;1264-1265 (f) Liu D.J., Zhang H., Grim P.C.M., De Feyter S., Wiesler U.M., Berresheim A.J., Müllen K., De Schryver F.C. Langmuir. 18:2002;2385-2391 (g) Lee M., Jeong Y.S., Cho B.K., Oh N.K., Zin W.C. Chem. Eur. J. 8:2002;876-883 (h) Dardel B., Guillon D., Heinrich B., Deschenaux R. J. Mater. Chem. 11:2001;2814-2831 (i) Marcos M., Gimenez R., Serrano J.L., Donnio B., Heinrich B., Guillon D. Chem. Eur. J. 7:2001;1006-1013.
52. For selected examples see: (a) Percec V., Ahn C.-H., Ungar G., Yeardley D.J.P., Möller M., Sheiko S.S. Nature. 391:1998;161-164 (b) Percec V., Cho W.-D., Mosier P.E., Ungar G., Yeardley D.J.P. J. Am. Chem. Soc. 120:1998;11061-11070 (c) Percec V., Cho W.D., Ungar G. J. Am. Chem. Soc. 122:2000;10273-10281 (d) Percec V., Cho W.D., Ungar G., Yeardley D.J.P. J. Am. Chem. Soc. 123:2002;1302-1315 (e) Schenning A.P.H.J., Jonkheijm P., Hofkens J., De Feyter S., Asavei T., Cotlet M., De Schryver F.C., Meijer E.W. Chem. Commun. 2002;1264-1265 (f) Liu D.J., Zhang H., Grim P.C.M., De Feyter S., Wiesler U.M., Berresheim A.J., Müllen K., De Schryver F.C. Langmuir. 18:2002;2385-2391 (g) Lee M., Jeong Y.S., Cho B.K., Oh N.K., Zin W.C. Chem. Eur. J. 8:2002;876-883 (h) Dardel B., Guillon D., Heinrich B., Deschenaux R. J. Mater. Chem. 11:2001;2814-2831 (i) Marcos M., Gimenez R., Serrano J.L., Donnio B., Heinrich B., Guillon D. Chem. Eur. J. 7:2001;1006-1013.
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57. See for example: (a) Newkome G.R., Güther R., Moorefield C.N., Cardullo F., Echegoyen L., Pérez-Cordero E., Luftmann H. Angew. Chem. Int. Ed. Engl. 34:1995;2023-2026 (b) Issberner J., Vögtle F., De Cola L., Balzani V. Chem. Eur. J. 3:1997;706-712 (c) Kawa M., Fréchet J.M.J. Chem. Mater. 10:1998;286-296 (d) Enomoto M., Aida T. J. Am. Chem. Soc. 121:1999;874-875 (e) Vögtle F., Plevoets M., Nieger M., Azzellini G.C., Credi A., De Cola L., De Marchis V., Venturi M., Balzani V. J. Am. Chem. Soc. 121:1999;6290-6298 (f) Newkome G.R., He E., Godínez L.A., Baker G.R. J. Am. Chem. Soc. 122:2000;9993-10006 (g) van Manen H.J., Fokkens R.H., Nibbering N.M.M., van Veggel F.C.J.M., Reinhoudt D.N. J. Org. Chem. 66:2001;4643-4650.
58. See for example: (a) Newkome G.R., Güther R., Moorefield C.N., Cardullo F., Echegoyen L., Pérez-Cordero E., Luftmann H. Angew. Chem. Int. Ed. Engl. 34:1995;2023-2026 (b) Issberner J., Vögtle F., De Cola L., Balzani V. Chem. Eur. J. 3:1997;706-712 (c) Kawa M., Fréchet J.M.J. Chem. Mater. 10:1998;286-296 (d) Enomoto M., Aida T. J. Am. Chem. Soc. 121:1999;874-875 (e) Vögtle F., Plevoets M., Nieger M., Azzellini G.C., Credi A., De Cola L., De Marchis V., Venturi M., Balzani V. J. Am. Chem. Soc. 121:1999;6290-6298 (f) Newkome G.R., He E., Godínez L.A., Baker G.R. J. Am. Chem. Soc. 122:2000;9993-10006 (g) van Manen H.J., Fokkens R.H., Nibbering N.M.M., van Veggel F.C.J.M., Reinhoudt D.N. J. Org. Chem. 66:2001;4643-4650.
59. See for example: (a) Newkome G.R., Güther R., Moorefield C.N., Cardullo F., Echegoyen L., Pérez-Cordero E., Luftmann H. Angew. Chem. Int. Ed. Engl. 34:1995;2023-2026 (b) Issberner J., Vögtle F., De Cola L., Balzani V. Chem. Eur. J. 3:1997;706-712 (c) Kawa M., Fréchet J.M.J. Chem. Mater. 10:1998;286-296 (d) Enomoto M., Aida T. J. Am. Chem. Soc. 121:1999;874-875 (e) Vögtle F., Plevoets M., Nieger M., Azzellini G.C., Credi A., De Cola L., De Marchis V., Venturi M., Balzani V. J. Am. Chem. Soc. 121:1999;6290-6298 (f) Newkome G.R., He E., Godínez L.A., Baker G.R. J. Am. Chem. Soc. 122:2000;9993-10006 (g) van Manen H.J., Fokkens R.H., Nibbering N.M.M., van Veggel F.C.J.M., Reinhoudt D.N. J. Org. Chem. 66:2001;4643-4650.
60. See for example: (a) Newkome G.R., Güther R., Moorefield C.N., Cardullo F., Echegoyen L., Pérez-Cordero E., Luftmann H. Angew. Chem. Int. Ed. Engl. 34:1995;2023-2026 (b) Issberner J., Vögtle F., De Cola L., Balzani V. Chem. Eur. J. 3:1997;706-712 (c) Kawa M., Fréchet J.M.J. Chem. Mater. 10:1998;286-296 (d) Enomoto M., Aida T. J. Am. Chem. Soc. 121:1999;874-875 (e) Vögtle F., Plevoets M., Nieger M., Azzellini G.C., Credi A., De Cola L., De Marchis V., Venturi M., Balzani V. J. Am. Chem. Soc. 121:1999;6290-6298 (f) Newkome G.R., He E., Godínez L.A., Baker G.R. J. Am. Chem. Soc. 122:2000;9993-10006 (g) van Manen H.J., Fokkens R.H., Nibbering N.M.M., van Veggel F.C.J.M., Reinhoudt D.N. J. Org. Chem. 66:2001;4643-4650.
61. See for example: (a) Newkome G.R., Güther R., Moorefield C.N., Cardullo F., Echegoyen L., Pérez-Cordero E., Luftmann H. Angew. Chem. Int. Ed. Engl. 34:1995;2023-2026 (b) Issberner J., Vögtle F., De Cola L., Balzani V. Chem. Eur. J. 3:1997;706-712 (c) Kawa M., Fréchet J.M.J. Chem. Mater. 10:1998;286-296 (d) Enomoto M., Aida T. J. Am. Chem. Soc. 121:1999;874-875 (e) Vögtle F., Plevoets M., Nieger M., Azzellini G.C., Credi A., De Cola L., De Marchis V., Venturi M., Balzani V. J. Am. Chem. Soc. 121:1999;6290-6298 (f) Newkome G.R., He E., Godínez L.A., Baker G.R. J. Am. Chem. Soc. 122:2000;9993-10006 (g) van Manen H.J., Fokkens R.H., Nibbering N.M.M., van Veggel F.C.J.M., Reinhoudt D.N. J. Org. Chem. 66:2001;4643-4650.
62. See for example: (a) Newkome G.R., Güther R., Moorefield C.N., Cardullo F., Echegoyen L., Pérez-Cordero E., Luftmann H. Angew. Chem. Int. Ed. Engl. 34:1995;2023-2026 (b) Issberner J., Vögtle F., De Cola L., Balzani V. Chem. Eur. J. 3:1997;706-712 (c) Kawa M., Fréchet J.M.J. Chem. Mater. 10:1998;286-296 (d) Enomoto M., Aida T. J. Am. Chem. Soc. 121:1999;874-875 (e) Vögtle F., Plevoets M., Nieger M., Azzellini G.C., Credi A., De Cola L., De Marchis V., Venturi M., Balzani V. J. Am. Chem. Soc. 121:1999;6290-6298 (f) Newkome G.R., He E., Godínez L.A., Baker G.R. J. Am. Chem. Soc. 122:2000;9993-10006 (g) van Manen H.J., Fokkens R.H., Nibbering N.M.M., van Veggel F.C.J.M., Reinhoudt D.N. J. Org. Chem. 66:2001;4643-4650.
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105. Bile acid-pyrene/trinitrofluorenone (aromatic donor-acceptor interactions): Maitra U., Kumar P.V., Chandra N., D'Sousa L.J., Prasanna M.D., Raju A.R. Chem. Commun. 1999;595-596.
106. Interactions between complementary glucopyranosides see: Jung J.H., Yoshida K., Shimizu T. Langmuir. 18:2002;8724-8727.
107. Keller O., Keller W.E., van Look G., Wersin G. Org. Synth. 63:1985;160-170.