Two-component dendritic gels: Easily tunable materials

Journal of the American Chemical Society

Volumn 125, Issue 30, 2003, Pages 9010-9011

  Hirst, Andrew R ^a   Smith, David K ^a   Feiters, Martin C ^b   Geurts, Huub P M ^b   Wright, Andrew C ^c  

^a UNIVERSITY OF YORK   (United Kingdom)

^b RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

^c GLYNDWR UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DENDRIMER; DIAMINE; ORGANIC SOLVENT; POLYMER; SOLVENT;

ACID BASE INTERACTION; ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CRYO SCANNING ELECTRON MICROSCOPY; DRUG DELIVERY SYSTEM; GEL; GELATION; PHASE TRANSITION; SCANNING ELECTRON MICROSCOPY; SUPRAMOLECULAR CHEMISTRY; THERMALLY REVERSIBLE GEL SOL PHASE TRANSITION; THERMODYNAMICS; TWO COMPONENT DENDRITIC GEL;

EID: 0042367619     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036111q     Document Type: Article

References (25)

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2. For reviews of small-molecule gelators, see: Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133-3159. van Esch, J. H.; Feringa, B. L. Angew. Chem., Int. Ed. 2000, 39, 2263-2266. Gronwald, O.; Snip, E.; Shinkai, S. Curr. Opin. Colloid Interface Sci. 2002, 7, 148-156.
3. For reviews of small-molecule gelators, see: Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133-3159. van Esch, J. H.; Feringa, B. L. Angew. Chem., Int. Ed. 2000, 39, 2263-2266. Gronwald, O.; Snip, E.; Shinkai, S. Curr. Opin. Colloid Interface Sci. 2002, 7, 148-156.
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5. For an overview, see: Beer, P. D.; Gale, P. A.; Smith, D. K. Supramolecular Chemistry; Oxford University Press: Oxford, UK, 1999.
6. Examples are too numerous to list here; see the excellent review articles in ref 1 for an introduction to this topic.
7. (a) Jang, W. D.; Jiang, D. L.; Aida, T. J. Am. Chem. Soc. 2000, 122, 3232-3233.
8. (b) Kim, C.; Kim, K. T.; Chang, Y.; Song, H. H.; Cho, T.-Y.; Jeon, H.-J. J. Am. Chem. Soc. 2001, 123, 5586-5587.
9. Two-component gels based on hydrogen bonding: (a) Hanabusa, K.; Miki, T.; Taguchi, Y.; Koyama, T.; Shirai, H. J. Chem. Soc., Chem. Commun. 1993, 1382-1384. (b) Jeong, S. W.; Shinkai, S. Nanotechnology 1997, 8, 179-185. (c) Inoue, K.; Ono, Y.; Kanekiyo, Y.; Ishi-i, T.; Yoshihara, K.; Shinkai, S. J. Org. Chem. 1999, 64, 2933-2937. (d) Tata, M.; John, V. T.; Waguespack, Y. Y.; McPherson, G. L. J. Am. Chem. Soc. 1994, 116, 9464-9470. (e) Simmons, B. A.; Taylor, C. E.; Landis, F. A.; John, V. T.; McPherson, G. L.; Schwartz, D. K.; Moore, R. J. Am. Chem. Soc. 2001, 123, 2414-2421. (f) Willemen, H. M.; Vermonden, T.; Marcelis, A. T. M.; Sudhölter, E. J. R. Langmuir 2002, 18, 7102-7106. (g) de Loos, M.; van Esch, J.; Kellogg, R. M.; Feringa, B. L. Angew. Chem., Int. Ed. 2001, 40, 613-616. (h) Nakano, K.; Hishikawa, Y.; Sada, K.; Miyata, M.; Hanabusa, K. Chem. Lett. 2000, 1170-1171.
10. Two-component gels based on hydrogen bonding: (a) Hanabusa, K.; Miki, T.; Taguchi, Y.; Koyama, T.; Shirai, H. J. Chem. Soc., Chem. Commun. 1993, 1382-1384. (b) Jeong, S. W.; Shinkai, S. Nanotechnology 1997, 8, 179-185. (c) Inoue, K.; Ono, Y.; Kanekiyo, Y.; Ishi-i, T.; Yoshihara, K.; Shinkai, S. J. Org. Chem. 1999, 64, 2933-2937. (d) Tata, M.; John, V. T.; Waguespack, Y. Y.; McPherson, G. L. J. Am. Chem. Soc. 1994, 116, 9464-9470. (e) Simmons, B. A.; Taylor, C. E.; Landis, F. A.; John, V. T.; McPherson, G. L.; Schwartz, D. K.; Moore, R. J. Am. Chem. Soc. 2001, 123, 2414-2421. (f) Willemen, H. M.; Vermonden, T.; Marcelis, A. T. M.; Sudhölter, E. J. R. Langmuir 2002, 18, 7102-7106. (g) de Loos, M.; van Esch, J.; Kellogg, R. M.; Feringa, B. L. Angew. Chem., Int. Ed. 2001, 40, 613-616. (h) Nakano, K.; Hishikawa, Y.; Sada, K.; Miyata, M.; Hanabusa, K. Chem. Lett. 2000, 1170-1171.
11. Two-component gels based on hydrogen bonding: (a) Hanabusa, K.; Miki, T.; Taguchi, Y.; Koyama, T.; Shirai, H. J. Chem. Soc., Chem. Commun. 1993, 1382-1384. (b) Jeong, S. W.; Shinkai, S. Nanotechnology 1997, 8, 179-185. (c) Inoue, K.; Ono, Y.; Kanekiyo, Y.; Ishi-i, T.; Yoshihara, K.; Shinkai, S. J. Org. Chem. 1999, 64, 2933-2937. (d) Tata, M.; John, V. T.; Waguespack, Y. Y.; McPherson, G. L. J. Am. Chem. Soc. 1994, 116, 9464-9470. (e) Simmons, B. A.; Taylor, C. E.; Landis, F. A.; John, V. T.; McPherson, G. L.; Schwartz, D. K.; Moore, R. J. Am. Chem. Soc. 2001, 123, 2414-2421. (f) Willemen, H. M.; Vermonden, T.; Marcelis, A. T. M.; Sudhölter, E. J. R. Langmuir 2002, 18, 7102-7106. (g) de Loos, M.; van Esch, J.; Kellogg, R. M.; Feringa, B. L. Angew. Chem., Int. Ed. 2001, 40, 613-616. (h) Nakano, K.; Hishikawa, Y.; Sada, K.; Miyata, M.; Hanabusa, K. Chem. Lett. 2000, 1170-1171.
12. Two-component gels based on hydrogen bonding: (a) Hanabusa, K.; Miki, T.; Taguchi, Y.; Koyama, T.; Shirai, H. J. Chem. Soc., Chem. Commun. 1993, 1382-1384. (b) Jeong, S. W.; Shinkai, S. Nanotechnology 1997, 8, 179-185. (c) Inoue, K.; Ono, Y.; Kanekiyo, Y.; Ishi-i, T.; Yoshihara, K.; Shinkai, S. J. Org. Chem. 1999, 64, 2933-2937. (d) Tata, M.; John, V. T.; Waguespack, Y. Y.; McPherson, G. L. J. Am. Chem. Soc. 1994, 116, 9464-9470. (e) Simmons, B. A.; Taylor, C. E.; Landis, F. A.; John, V. T.; McPherson, G. L.; Schwartz, D. K.; Moore, R. J. Am. Chem. Soc. 2001, 123, 2414-2421. (f) Willemen, H. M.; Vermonden, T.; Marcelis, A. T. M.; Sudhölter, E. J. R. Langmuir 2002, 18, 7102-7106. (g) de Loos, M.; van Esch, J.; Kellogg, R. M.; Feringa, B. L. Angew. Chem., Int. Ed. 2001, 40, 613-616. (h) Nakano, K.; Hishikawa, Y.; Sada, K.; Miyata, M.; Hanabusa, K. Chem. Lett. 2000, 1170-1171.
13. Two-component gels based on hydrogen bonding: (a) Hanabusa, K.; Miki, T.; Taguchi, Y.; Koyama, T.; Shirai, H. J. Chem. Soc., Chem. Commun. 1993, 1382-1384. (b) Jeong, S. W.; Shinkai, S. Nanotechnology 1997, 8, 179-185. (c) Inoue, K.; Ono, Y.; Kanekiyo, Y.; Ishi-i, T.; Yoshihara, K.; Shinkai, S. J. Org. Chem. 1999, 64, 2933-2937. (d) Tata, M.; John, V. T.; Waguespack, Y. Y.; McPherson, G. L. J. Am. Chem. Soc. 1994, 116, 9464-9470. (e) Simmons, B. A.; Taylor, C. E.; Landis, F. A.; John, V. T.; McPherson, G. L.; Schwartz, D. K.; Moore, R. J. Am. Chem. Soc. 2001, 123, 2414-2421. (f) Willemen, H. M.; Vermonden, T.; Marcelis, A. T. M.; Sudhölter, E. J. R. Langmuir 2002, 18, 7102-7106. (g) de Loos, M.; van Esch, J.; Kellogg, R. M.; Feringa, B. L. Angew. Chem., Int. Ed. 2001, 40, 613-616. (h) Nakano, K.; Hishikawa, Y.; Sada, K.; Miyata, M.; Hanabusa, K. Chem. Lett. 2000, 1170-1171.
14. Two-component gels based on hydrogen bonding: (a) Hanabusa, K.; Miki, T.; Taguchi, Y.; Koyama, T.; Shirai, H. J. Chem. Soc., Chem. Commun. 1993, 1382-1384. (b) Jeong, S. W.; Shinkai, S. Nanotechnology 1997, 8, 179-185. (c) Inoue, K.; Ono, Y.; Kanekiyo, Y.; Ishi-i, T.; Yoshihara, K.; Shinkai, S. J. Org. Chem. 1999, 64, 2933-2937. (d) Tata, M.; John, V. T.; Waguespack, Y. Y.; McPherson, G. L. J. Am. Chem. Soc. 1994, 116, 9464-9470. (e) Simmons, B. A.; Taylor, C. E.; Landis, F. A.; John, V. T.; McPherson, G. L.; Schwartz, D. K.; Moore, R. J. Am. Chem. Soc. 2001, 123, 2414-2421. (f) Willemen, H. M.; Vermonden, T.; Marcelis, A. T. M.; Sudhölter, E. J. R. Langmuir 2002, 18, 7102-7106. (g) de Loos, M.; van Esch, J.; Kellogg, R. M.; Feringa, B. L. Angew. Chem., Int. Ed. 2001, 40, 613-616. (h) Nakano, K.; Hishikawa, Y.; Sada, K.; Miyata, M.; Hanabusa, K. Chem. Lett. 2000, 1170-1171.
15. Two-component gels based on hydrogen bonding: (a) Hanabusa, K.; Miki, T.; Taguchi, Y.; Koyama, T.; Shirai, H. J. Chem. Soc., Chem. Commun. 1993, 1382-1384. (b) Jeong, S. W.; Shinkai, S. Nanotechnology 1997, 8, 179-185. (c) Inoue, K.; Ono, Y.; Kanekiyo, Y.; Ishi-i, T.; Yoshihara, K.; Shinkai, S. J. Org. Chem. 1999, 64, 2933-2937. (d) Tata, M.; John, V. T.; Waguespack, Y. Y.; McPherson, G. L. J. Am. Chem. Soc. 1994, 116, 9464-9470. (e) Simmons, B. A.; Taylor, C. E.; Landis, F. A.; John, V. T.; McPherson, G. L.; Schwartz, D. K.; Moore, R. J. Am. Chem. Soc. 2001, 123, 2414-2421. (f) Willemen, H. M.; Vermonden, T.; Marcelis, A. T. M.; Sudhölter, E. J. R. Langmuir 2002, 18, 7102-7106. (g) de Loos, M.; van Esch, J.; Kellogg, R. M.; Feringa, B. L. Angew. Chem., Int. Ed. 2001, 40, 613-616. (h) Nakano, K.; Hishikawa, Y.; Sada, K.; Miyata, M.; Hanabusa, K. Chem. Lett. 2000, 1170-1171.
16. Two-component gels based on hydrogen bonding: (a) Hanabusa, K.; Miki, T.; Taguchi, Y.; Koyama, T.; Shirai, H. J. Chem. Soc., Chem. Commun. 1993, 1382-1384. (b) Jeong, S. W.; Shinkai, S. Nanotechnology 1997, 8, 179-185. (c) Inoue, K.; Ono, Y.; Kanekiyo, Y.; Ishi-i, T.; Yoshihara, K.; Shinkai, S. J. Org. Chem. 1999, 64, 2933-2937. (d) Tata, M.; John, V. T.; Waguespack, Y. Y.; McPherson, G. L. J. Am. Chem. Soc. 1994, 116, 9464-9470. (e) Simmons, B. A.; Taylor, C. E.; Landis, F. A.; John, V. T.; McPherson, G. L.; Schwartz, D. K.; Moore, R. J. Am. Chem. Soc. 2001, 123, 2414-2421. (f) Willemen, H. M.; Vermonden, T.; Marcelis, A. T. M.; Sudhölter, E. J. R. Langmuir 2002, 18, 7102-7106. (g) de Loos, M.; van Esch, J.; Kellogg, R. M.; Feringa, B. L. Angew. Chem., Int. Ed. 2001, 40, 613-616. (h) Nakano, K.; Hishikawa, Y.; Sada, K.; Miyata, M.; Hanabusa, K. Chem. Lett. 2000, 1170-1171.
17. Two-component gels based on 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. (b) Friggeri, A.; Gronwald, O.; van Bommel, K. J. C.; Shinkai, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2002, 124, 10754-10758. (c) Babu, P.; Sangeetha, N. M.; Vijaykumar, P.; Maitra, U.; Rissanen, K.; Raju, A. R. Chem. Eur. J. 2003, 9, 1922-1932.
18. Two-component gels based on 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. (b) Friggeri, A.; Gronwald, O.; van Bommel, K. J. C.; Shinkai, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2002, 124, 10754-10758. (c) Babu, P.; Sangeetha, N. M.; Vijaykumar, P.; Maitra, U.; Rissanen, K.; Raju, A. R. Chem. Eur. J. 2003, 9, 1922-1932.
19. Two-component gels based on 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. (b) Friggeri, A.; Gronwald, O.; van Bommel, K. J. C.; Shinkai, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2002, 124, 10754-10758. (c) Babu, P.; Sangeetha, N. M.; Vijaykumar, P.; Maitra, U.; Rissanen, K.; Raju, A. R. Chem. Eur. J. 2003, 9, 1922-1932.
20. Two-component gels based on a reversible chemical reaction give rise to latent gels: (a) George, M.; Weiss, R. G. Langmuir 2003, 19, 1017-1025. (b) George, M.; Weiss, R. G. Langmuir 2002, 18, 7124-7135.
21. Two-component gels based on a reversible chemical reaction give rise to latent gels: (a) George, M.; Weiss, R. G. Langmuir 2003, 19, 1017-1025. (b) George, M.; Weiss, R. G. Langmuir 2002, 18, 7124-7135.
22. For our initial report of two-component dendritic gelator systems, see: Partridge, K. S.; Smith, D. K.; Dykes, G. M.; McGrail, P. T. Chem. Commun. 2001, 319-320. For a paper in which the design principle is extended to dendritic crown ethers and aliphatic bis-ammonium cations, see: Dykes, G. M.; Smith, D. K. Tetrahedron 2003, 59, 3999-4009.
23. For our initial report of two-component dendritic gelator systems, see: Partridge, K. S.; Smith, D. K.; Dykes, G. M.; McGrail, P. T. Chem. Commun. 2001, 319-320. For a paper in which the design principle is extended to dendritic crown ethers and aliphatic bis-ammonium cations, see: Dykes, G. M.; Smith, D. K. Tetrahedron 2003, 59, 3999-4009.
24. gel values.
25. For a review of organogel applications, see: Hinze, W. L.; Uemasu, I.; Dai, F.; Braun, J. M. Curr. Opin. Colloid Interface Sci. 1996, 1, 502-513.