Molecular Tectonics. Dendritic Construction of Porous Hydrogen-Bonded Networks

Organic Letters

Volumn 5, Issue 25, 2003, Pages 4787-4790

  Laliberté, Dominic ^a   Maris, Thierry ^a   Sirois, Ariane ^a   Wuest, James D ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DENDRIMER; DIPENTAERYTHRITYLHEXAPHENYL ETHER; ETHER DERIVATIVE; HYDROGEN; PENTAERYTHRITYLTETRAPHENYL ETHER; UNCLASSIFIED DRUG;

ARTICLE; HYDROGEN BOND; MOLECULE; POROSITY;

EID: 0347052795     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035712j     Document Type: Article

References (40)

1. Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696.
2. Fournier, J.-H.; Maris, T.; Wuest, J. D.; Guo, W.; Galoppini, E. J. Am. Chem. Soc. 2003, 125, 1002.
3. Sauriat-Dorizon, H.; Maris, T.; Wuest, J. D.; Enright, G. D. J. Org. Chem. 2003, 68, 240.
4. Laliberté, D.; Maris, T.; Wuest, J. D. J. Org. Chem., accepted for publication.
5. For references to related work, see: Fournier, J.-H.; Maris, T.; Wuest, J. D. J. Org. Chem., in press. Fournier, J.-H.; Maris, T.; Simard, M.; Wuest, J. D. Cryst. Growth Des. 2003, 3, 535.
6. For references to related work, see: Fournier, J.-H.; Maris, T.; Wuest, J. D. J. Org. Chem., in press. Fournier, J.-H.; Maris, T.; Simard, M.; Wuest, J. D. Cryst. Growth Des. 2003, 3, 535.
7. 2-5
8. Spek, A. L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, The Netherlands, 2001. van der Sluis, P.; Spek, A. L. Acta Crystallogr. 1990, A46, 194.
9. Spek, A. L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, The Netherlands, 2001. van der Sluis, P.; Spek, A. L. Acta Crystallogr. 1990, A46, 194.
10. The dimensions of a channel in a particular direction correspond to the cross section of an imaginary cylinder that could be passed through the hypothetical open network in the given direction in contact with the van der Waals surface. Such values are inherently conservative because (1) they measure the cross section at the most narrow constriction, and (2) they systematically underestimate the sizes of channels that are not uniform and linear.
11. Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendrimers and Dendrons: Concepts, Syntheses, Applications; VCH: Weinheim, Germany, 2001.
12. For other recent reviews of the subject of dendrimers, see: Grayson, S. M.; Fréchet, J. M. J. Chem. Rev. 2001, 101, 3819. Chow, H.-F.; Leung, C.-F.; Wang, G.-X.; Zhang, J. Top. Curr. Chem. 2001, 217, 1. Zimmerman, S. C.; Lawless, L. J. Top. Curr. Chem. 2001, 217, 95. Vögtle, F.; Gestermann, S.; Hesse, R.; Schwierz, H.; Windisch, B. Prog. Polym. Sci. 2000, 25, 987.
13. For other recent reviews of the subject of dendrimers, see: Grayson, S. M.; Fréchet, J. M. J. Chem. Rev. 2001, 101, 3819. Chow, H.-F.; Leung, C.-F.; Wang, G.-X.; Zhang, J. Top. Curr. Chem. 2001, 217, 1. Zimmerman, S. C.; Lawless, L. J. Top. Curr. Chem. 2001, 217, 95. Vögtle, F.; Gestermann, S.; Hesse, R.; Schwierz, H.; Windisch, B. Prog. Polym. Sci. 2000, 25, 987.
14. For other recent reviews of the subject of dendrimers, see: Grayson, S. M.; Fréchet, J. M. J. Chem. Rev. 2001, 101, 3819. Chow, H.-F.; Leung, C.-F.; Wang, G.-X.; Zhang, J. Top. Curr. Chem. 2001, 217, 1. Zimmerman, S. C.; Lawless, L. J. Top. Curr. Chem. 2001, 217, 95. Vögtle, F.; Gestermann, S.; Hesse, R.; Schwierz, H.; Windisch, B. Prog. Polym. Sci. 2000, 25, 987.
15. For other recent reviews of the subject of dendrimers, see: Grayson, S. M.; Fréchet, J. M. J. Chem. Rev. 2001, 101, 3819. Chow, H.-F.; Leung, C.-F.; Wang, G.-X.; Zhang, J. Top. Curr. Chem. 2001, 217, 1. Zimmerman, S. C.; Lawless, L. J. Top. Curr. Chem. 2001, 217, 95. Vögtle, F.; Gestermann, S.; Hesse, R.; Schwierz, H.; Windisch, B. Prog. Polym. Sci. 2000, 25, 987.
16. For recent use of derivatives of dipentaerythritol in materials science, see: Shukla, A. A.; Bae, S. S.; Moore, J. A.; Barnthouse, K. A.; Cramer, S. M. Ind. Eng. Chem. Res. 1998, 37, 4090.
17. For other recent uses of derivatives of dipentaerythritol in materials science, see: Biela, T.; Duda, A.; Rode, K.; Pasch, H. Polymer 2003, 44, 1851. Gigant, K.; Posset, U.; Schottner, G.; Baia, L.; Kiefer, W.; Popp, J. J. Sol-Gel Sci. Technol. 2003, 26, 369. Mayadunne, R. T. A.; Moad, G.; Rizzardo, E. Tetrahedron Lett. 2002, 43, 6811. Rohr, T.; Knaus, S.; Gruber, H.; Sherrington, D. C. Macromolecules 2002, 35, 97. Kader, M. A.; Bhowmick, A. K.; Inoue, T.; Chiba, T. J. Mater. Sci. 2002, 37, 1503. Kaczmarek, H.; Ołdak, D.; Szalla, A. J. Appl. Polym. Sci. 2002, 86, 3725. Huang, H.; Zhang, J.-Z.; Shi, W.-F. J. Appl. Polym. Sci. 2001, 80, 499. Joziasse, C. A. P.; Grablowitz, H.; Pennings, A. J. Macromol. Chem. Phys. 2000, 201, 107. Bunning, T. J.; Kirkpatrick, S. M.; Natarajan, L. V.; Tondiglia, V. P.; Tomlin, D. W. Chem. Mater. 2000, 12, 2842. Menger, F. M.; Migulin, V. A. J. Org. Chem. 1999, 64, 8916.
18. For other recent uses of derivatives of dipentaerythritol in materials science, see: Biela, T.; Duda, A.; Rode, K.; Pasch, H. Polymer 2003, 44, 1851. Gigant, K.; Posset, U.; Schottner, G.; Baia, L.; Kiefer, W.; Popp, J. J. Sol-Gel Sci. Technol. 2003, 26, 369. Mayadunne, R. T. A.; Moad, G.; Rizzardo, E. Tetrahedron Lett. 2002, 43, 6811. Rohr, T.; Knaus, S.; Gruber, H.; Sherrington, D. C. Macromolecules 2002, 35, 97. Kader, M. A.; Bhowmick, A. K.; Inoue, T.; Chiba, T. J. Mater. Sci. 2002, 37, 1503. Kaczmarek, H.; Ołdak, D.; Szalla, A. J. Appl. Polym. Sci. 2002, 86, 3725. Huang, H.; Zhang, J.-Z.; Shi, W.-F. J. Appl. Polym. Sci. 2001, 80, 499. Joziasse, C. A. P.; Grablowitz, H.; Pennings, A. J. Macromol. Chem. Phys. 2000, 201, 107. Bunning, T. J.; Kirkpatrick, S. M.; Natarajan, L. V.; Tondiglia, V. P.; Tomlin, D. W. Chem. Mater. 2000, 12, 2842. Menger, F. M.; Migulin, V. A. J. Org. Chem. 1999, 64, 8916.
19. For other recent uses of derivatives of dipentaerythritol in materials science, see: Biela, T.; Duda, A.; Rode, K.; Pasch, H. Polymer 2003, 44, 1851. Gigant, K.; Posset, U.; Schottner, G.; Baia, L.; Kiefer, W.; Popp, J. J. Sol-Gel Sci. Technol. 2003, 26, 369. Mayadunne, R. T. A.; Moad, G.; Rizzardo, E. Tetrahedron Lett. 2002, 43, 6811. Rohr, T.; Knaus, S.; Gruber, H.; Sherrington, D. C. Macromolecules 2002, 35, 97. Kader, M. A.; Bhowmick, A. K.; Inoue, T.; Chiba, T. J. Mater. Sci. 2002, 37, 1503. Kaczmarek, H.; Ołdak, D.; Szalla, A. J. Appl. Polym. Sci. 2002, 86, 3725. Huang, H.; Zhang, J.-Z.; Shi, W.-F. J. Appl. Polym. Sci. 2001, 80, 499. Joziasse, C. A. P.; Grablowitz, H.; Pennings, A. J. Macromol. Chem. Phys. 2000, 201, 107. Bunning, T. J.; Kirkpatrick, S. M.; Natarajan, L. V.; Tondiglia, V. P.; Tomlin, D. W. Chem. Mater. 2000, 12, 2842. Menger, F. M.; Migulin, V. A. J. Org. Chem. 1999, 64, 8916.
20. For other recent uses of derivatives of dipentaerythritol in materials science, see: Biela, T.; Duda, A.; Rode, K.; Pasch, H. Polymer 2003, 44, 1851. Gigant, K.; Posset, U.; Schottner, G.; Baia, L.; Kiefer, W.; Popp, J. J. Sol-Gel Sci. Technol. 2003, 26, 369. Mayadunne, R. T. A.; Moad, G.; Rizzardo, E. Tetrahedron Lett. 2002, 43, 6811. Rohr, T.; Knaus, S.; Gruber, H.; Sherrington, D. C. Macromolecules 2002, 35, 97. Kader, M. A.; Bhowmick, A. K.; Inoue, T.; Chiba, T. J. Mater. Sci. 2002, 37, 1503. Kaczmarek, H.; Ołdak, D.; Szalla, A. J. Appl. Polym. Sci. 2002, 86, 3725. Huang, H.; Zhang, J.-Z.; Shi, W.-F. J. Appl. Polym. Sci. 2001, 80, 499. Joziasse, C. A. P.; Grablowitz, H.; Pennings, A. J. Macromol. Chem. Phys. 2000, 201, 107. Bunning, T. J.; Kirkpatrick, S. M.; Natarajan, L. V.; Tondiglia, V. P.; Tomlin, D. W. Chem. Mater. 2000, 12, 2842. Menger, F. M.; Migulin, V. A. J. Org. Chem. 1999, 64, 8916.
21. For other recent uses of derivatives of dipentaerythritol in materials science, see: Biela, T.; Duda, A.; Rode, K.; Pasch, H. Polymer 2003, 44, 1851. Gigant, K.; Posset, U.; Schottner, G.; Baia, L.; Kiefer, W.; Popp, J. J. Sol-Gel Sci. Technol. 2003, 26, 369. Mayadunne, R. T. A.; Moad, G.; Rizzardo, E. Tetrahedron Lett. 2002, 43, 6811. Rohr, T.; Knaus, S.; Gruber, H.; Sherrington, D. C. Macromolecules 2002, 35, 97. Kader, M. A.; Bhowmick, A. K.; Inoue, T.; Chiba, T. J. Mater. Sci. 2002, 37, 1503. Kaczmarek, H.; Ołdak, D.; Szalla, A. J. Appl. Polym. Sci. 2002, 86, 3725. Huang, H.; Zhang, J.-Z.; Shi, W.-F. J. Appl. Polym. Sci. 2001, 80, 499. Joziasse, C. A. P.; Grablowitz, H.; Pennings, A. J. Macromol. Chem. Phys. 2000, 201, 107. Bunning, T. J.; Kirkpatrick, S. M.; Natarajan, L. V.; Tondiglia, V. P.; Tomlin, D. W. Chem. Mater. 2000, 12, 2842. Menger, F. M.; Migulin, V. A. J. Org. Chem. 1999, 64, 8916.
22. For other recent uses of derivatives of dipentaerythritol in materials science, see: Biela, T.; Duda, A.; Rode, K.; Pasch, H. Polymer 2003, 44, 1851. Gigant, K.; Posset, U.; Schottner, G.; Baia, L.; Kiefer, W.; Popp, J. J. Sol-Gel Sci. Technol. 2003, 26, 369. Mayadunne, R. T. A.; Moad, G.; Rizzardo, E. Tetrahedron Lett. 2002, 43, 6811. Rohr, T.; Knaus, S.; Gruber, H.; Sherrington, D. C. Macromolecules 2002, 35, 97. Kader, M. A.; Bhowmick, A. K.; Inoue, T.; Chiba, T. J. Mater. Sci. 2002, 37, 1503. Kaczmarek, H.; Ołdak, D.; Szalla, A. J. Appl. Polym. Sci. 2002, 86, 3725. Huang, H.; Zhang, J.-Z.; Shi, W.-F. J. Appl. Polym. Sci. 2001, 80, 499. Joziasse, C. A. P.; Grablowitz, H.; Pennings, A. J. Macromol. Chem. Phys. 2000, 201, 107. Bunning, T. J.; Kirkpatrick, S. M.; Natarajan, L. V.; Tondiglia, V. P.; Tomlin, D. W. Chem. Mater. 2000, 12, 2842. Menger, F. M.; Migulin, V. A. J. Org. Chem. 1999, 64, 8916.
23. For other recent uses of derivatives of dipentaerythritol in materials science, see: Biela, T.; Duda, A.; Rode, K.; Pasch, H. Polymer 2003, 44, 1851. Gigant, K.; Posset, U.; Schottner, G.; Baia, L.; Kiefer, W.; Popp, J. J. Sol-Gel Sci. Technol. 2003, 26, 369. Mayadunne, R. T. A.; Moad, G.; Rizzardo, E. Tetrahedron Lett. 2002, 43, 6811. Rohr, T.; Knaus, S.; Gruber, H.; Sherrington, D. C. Macromolecules 2002, 35, 97. Kader, M. A.; Bhowmick, A. K.; Inoue, T.; Chiba, T. J. Mater. Sci. 2002, 37, 1503. Kaczmarek, H.; Ołdak, D.; Szalla, A. J. Appl. Polym. Sci. 2002, 86, 3725. Huang, H.; Zhang, J.-Z.; Shi, W.-F. J. Appl. Polym. Sci. 2001, 80, 499. Joziasse, C. A. P.; Grablowitz, H.; Pennings, A. J. Macromol. Chem. Phys. 2000, 201, 107. Bunning, T. J.; Kirkpatrick, S. M.; Natarajan, L. V.; Tondiglia, V. P.; Tomlin, D. W. Chem. Mater. 2000, 12, 2842. Menger, F. M.; Migulin, V. A. J. Org. Chem. 1999, 64, 8916.
24. For other recent uses of derivatives of dipentaerythritol in materials science, see: Biela, T.; Duda, A.; Rode, K.; Pasch, H. Polymer 2003, 44, 1851. Gigant, K.; Posset, U.; Schottner, G.; Baia, L.; Kiefer, W.; Popp, J. J. Sol-Gel Sci. Technol. 2003, 26, 369. Mayadunne, R. T. A.; Moad, G.; Rizzardo, E. Tetrahedron Lett. 2002, 43, 6811. Rohr, T.; Knaus, S.; Gruber, H.; Sherrington, D. C. Macromolecules 2002, 35, 97. Kader, M. A.; Bhowmick, A. K.; Inoue, T.; Chiba, T. J. Mater. Sci. 2002, 37, 1503. Kaczmarek, H.; Ołdak, D.; Szalla, A. J. Appl. Polym. Sci. 2002, 86, 3725. Huang, H.; Zhang, J.-Z.; Shi, W.-F. J. Appl. Polym. Sci. 2001, 80, 499. Joziasse, C. A. P.; Grablowitz, H.; Pennings, A. J. Macromol. Chem. Phys. 2000, 201, 107. Bunning, T. J.; Kirkpatrick, S. M.; Natarajan, L. V.; Tondiglia, V. P.; Tomlin, D. W. Chem. Mater. 2000, 12, 2842. Menger, F. M.; Migulin, V. A. J. Org. Chem. 1999, 64, 8916.
25. For other recent uses of derivatives of dipentaerythritol in materials science, see: Biela, T.; Duda, A.; Rode, K.; Pasch, H. Polymer 2003, 44, 1851. Gigant, K.; Posset, U.; Schottner, G.; Baia, L.; Kiefer, W.; Popp, J. J. Sol-Gel Sci. Technol. 2003, 26, 369. Mayadunne, R. T. A.; Moad, G.; Rizzardo, E. Tetrahedron Lett. 2002, 43, 6811. Rohr, T.; Knaus, S.; Gruber, H.; Sherrington, D. C. Macromolecules 2002, 35, 97. Kader, M. A.; Bhowmick, A. K.; Inoue, T.; Chiba, T. J. Mater. Sci. 2002, 37, 1503. Kaczmarek, H.; Ołdak, D.; Szalla, A. J. Appl. Polym. Sci. 2002, 86, 3725. Huang, H.; Zhang, J.-Z.; Shi, W.-F. J. Appl. Polym. Sci. 2001, 80, 499. Joziasse, C. A. P.; Grablowitz, H.; Pennings, A. J. Macromol. Chem. Phys. 2000, 201, 107. Bunning, T. J.; Kirkpatrick, S. M.; Natarajan, L. V.; Tondiglia, V. P.; Tomlin, D. W. Chem. Mater. 2000, 12, 2842. Menger, F. M.; Migulin, V. A. J. Org. Chem. 1999, 64, 8916.
26. For other recent uses of derivatives of dipentaerythritol in materials science, see: Biela, T.; Duda, A.; Rode, K.; Pasch, H. Polymer 2003, 44, 1851. Gigant, K.; Posset, U.; Schottner, G.; Baia, L.; Kiefer, W.; Popp, J. J. Sol-Gel Sci. Technol. 2003, 26, 369. Mayadunne, R. T. A.; Moad, G.; Rizzardo, E. Tetrahedron Lett. 2002, 43, 6811. Rohr, T.; Knaus, S.; Gruber, H.; Sherrington, D. C. Macromolecules 2002, 35, 97. Kader, M. A.; Bhowmick, A. K.; Inoue, T.; Chiba, T. J. Mater. Sci. 2002, 37, 1503. Kaczmarek, H.; Ołdak, D.; Szalla, A. J. Appl. Polym. Sci. 2002, 86, 3725. Huang, H.; Zhang, J.-Z.; Shi, W.-F. J. Appl. Polym. Sci. 2001, 80, 499. Joziasse, C. A. P.; Grablowitz, H.; Pennings, A. J. Macromol. Chem. Phys. 2000, 201, 107. Bunning, T. J.; Kirkpatrick, S. M.; Natarajan, L. V.; Tondiglia, V. P.; Tomlin, D. W. Chem. Mater. 2000, 12, 2842. Menger, F. M.; Migulin, V. A. J. Org. Chem. 1999, 64, 8916.
27. Dipentaerythritol and tripentaerythritol are commercially available and inexpensive. For preparations of tetrapentaerythritol and pentapentaerythritol, see: Padias, A. B.; Hall, H. K., Jr.; Tomalia, D. A.; McConnell, J. R. J. Org. Chem. 1987, 52, 5305. Suchanec, R. R. Anal. Chem. 1965, 37, 1361.
28. Dipentaerythritol and tripentaerythritol are commercially available and inexpensive. For preparations of tetrapentaerythritol and pentapentaerythritol, see: Padias, A. B.; Hall, H. K., Jr.; Tomalia, D. A.; McConnell, J. R. J. Org. Chem. 1987, 52, 5305. Suchanec, R. R. Anal. Chem. 1965, 37, 1361.
29. For recent reviews of dendritic encapsulation, see: Gorman, C. B.; Smith, J. C. Acc. Chem. Res. 2001, 34, 60. Hecht, S.; Fréchet, J. M. J. Angew. Chem., Int. Ed. 2001, 40, 74.
30. For recent reviews of dendritic encapsulation, see: Gorman, C. B.; Smith, J. C. Acc. Chem. Res. 2001, 34, 60. Hecht, S.; Fréchet, J. M. J. Angew. Chem., Int. Ed. 2001, 40, 74.
31. For structural studies of derivatives of dipentaerythritol by X-ray crystallography, see: Nättinen, K. I.; Rissanen, K. Cryst. Growth Des. 2003, 3, 339.
32. For other recent structural studies of dendritic molecules by single-crystal X-ray diffraction, see: Bauer, R. E.; Enkelmann, V.; Wiesler, U. M.; Berresheim, A. J.; Müllen, K. Chem. Eur. J. 2002, 8, 3858. Ranganathan, D.; Kurur, S.; Gilardi, R.; Karle, I. L. Biopolymers 2000, 54, 289. Friedmann, G.; Guilbert, Y.; Wittmann, J. C. Eur. Polym. J. 1999, 35, 1097.
33. For other recent structural studies of dendritic molecules by single-crystal X-ray diffraction, see: Bauer, R. E.; Enkelmann, V.; Wiesler, U. M.; Berresheim, A. J.; Müllen, K. Chem. Eur. J. 2002, 8, 3858. Ranganathan, D.; Kurur, S.; Gilardi, R.; Karle, I. L. Biopolymers 2000, 54, 289. Friedmann, G.; Guilbert, Y.; Wittmann, J. C. Eur. Polym. J. 1999, 35, 1097.
34. For other recent structural studies of dendritic molecules by single-crystal X-ray diffraction, see: Bauer, R. E.; Enkelmann, V.; Wiesler, U. M.; Berresheim, A. J.; Müllen, K. Chem. Eur. J. 2002, 8, 3858. Ranganathan, D.; Kurur, S.; Gilardi, R.; Karle, I. L. Biopolymers 2000, 54, 289. Friedmann, G.; Guilbert, Y.; Wittmann, J. C. Eur. Polym. J. 1999, 35, 1097.
35. For the structure of hexatosylate 8, see the Supporting Information.
36. Simons, J. K.; Saxton, M. R Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, p 78.
37. 2 = 0.2195, and GoF = 1.041. Details are provided as Supporting Information.
38. 2O included could not be determined accurately.
39. 15
40. Joining the central oxygen atom of each tecton with the centers of the six neighboring tectons defines a complex noninterpenetrated six-connected network (see Supporting Information).