Assembly of a supramolecular capsule on a molecular printboard

Journal of the American Chemical Society

Volumn 126, Issue 51, 2004, Pages 17050-17058

  Corbellini, Francesca ^a   Mulder, Alart ^a   Sartori, Andrea ^a,b   Ludden, Manon J W ^a   Casnati, Alessandro ^b,c   Ungaro, Rocco ^b,c   Huskens, Jurriaan ^a   Crego Calama, Mercedes ^a   Reinhoudt, David N ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

^b UNIVERSITY OF PARMA   (Italy)

^c NONE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ASSEMBLY; IONIC STRENGTH; MONOLAYERS; NUCLEAR MAGNETIC RESONANCE; SOLUTIONS; SPECTROSCOPY; SURFACE PLASMON RESONANCE; TITRATION;

ARENE; IONIC INTERACTIONS; MOLECULAR CAPSULE; PRINTBOARD;

SUPRAMOLECULAR CHEMISTRY;

2 PROPANOL; BETA CYCLODEXTRIN; CALIXARENE; GOLD; TETRAGUANIDINIUM CALIX[4]ARENE; TETRASULFONATE CALIX[4]ARENE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; BINDING AFFINITY; DESORPTION; DRUG CAPSULE; ELECTRICITY; ELECTROSPRAY MASS SPECTROMETRY; IONIC STRENGTH; ISOTHERMAL TITRATION CALORIMETRY; MOLECULAR INTERACTION; MOLECULE; MONITORING; PROTON NUCLEAR MAGNETIC RESONANCE; SURFACE PLASMON RESONANCE; SURFACE PROPERTY;

EID: 11244281035     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja046780j     Document Type: Article

References (106)

1. (a) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229-2260.
2. (b) Greig, L. M.; Philp, D. Chem. Soc. Rev. 2001, 30, 287-302.
3. (c) Higler, I.; Timmerman, P.; Verboom, W.; Reinhoudt, D. N. Eur. J. Org. Chem. 1998, 2689-2702.
4. (d) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2382-2426.
5. (e) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem Rev. 2000, 100, 853-908.
6. (f) Stang, P. J.; Olenyuk, B. Acc. Chem. Res. 1997, 30, 502-518.
7. (g) Olenyuk, B.; Fechtenkötter, A.; Stang, P. J. J. Chem, Soc., Dalton Trans. 1998, 1707-1728.
8. For reviews on molecular containers, see: (a) Conn, M. M.; Rebek, J., Jr. Chem, Rev. 1997, 97, 1647-1668. (b) MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. 1999, 38, 1018-1033. (c) Rudkevich, D. M. Bull Chem. Soc. Jpn. 2002, 75, 393-413. (d) Hof, F.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2002, 41, 1488-1508. (e) Jasat, A.; Sherman, J. C. Chem. Rev. 1999, 99, 931-967. (f) Russel-Seidel, S.; Stang, P. J. Acc. Chem. Res. 2002, 35, 972-983.
9. For reviews on molecular containers, see: (a) Conn, M. M.; Rebek, J., Jr. Chem, Rev. 1997, 97, 1647-1668. (b) MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. 1999, 38, 1018-1033. (c) Rudkevich, D. M. Bull Chem. Soc. Jpn. 2002, 75, 393-413. (d) Hof, F.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2002, 41, 1488-1508. (e) Jasat, A.; Sherman, J. C. Chem. Rev. 1999, 99, 931-967. (f) Russel-Seidel, S.; Stang, P. J. Acc. Chem. Res. 2002, 35, 972-983.
10. For reviews on molecular containers, see: (a) Conn, M. M.; Rebek, J., Jr. Chem, Rev. 1997, 97, 1647-1668. (b) MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. 1999, 38, 1018-1033. (c) Rudkevich, D. M. Bull Chem. Soc. Jpn. 2002, 75, 393-413. (d) Hof, F.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2002, 41, 1488-1508. (e) Jasat, A.; Sherman, J. C. Chem. Rev. 1999, 99, 931-967. (f) Russel-Seidel, S.; Stang, P. J. Acc. Chem. Res. 2002, 35, 972-983.
11. For reviews on molecular containers, see: (a) Conn, M. M.; Rebek, J., Jr. Chem, Rev. 1997, 97, 1647-1668. (b) MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. 1999, 38, 1018-1033. (c) Rudkevich, D. M. Bull Chem. Soc. Jpn. 2002, 75, 393-413. (d) Hof, F.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2002, 41, 1488-1508. (e) Jasat, A.; Sherman, J. C. Chem. Rev. 1999, 99, 931-967. (f) Russel-Seidel, S.; Stang, P. J. Acc. Chem. Res. 2002, 35, 972-983.
12. For reviews on molecular containers, see: (a) Conn, M. M.; Rebek, J., Jr. Chem, Rev. 1997, 97, 1647-1668. (b) MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. 1999, 38, 1018-1033. (c) Rudkevich, D. M. Bull Chem. Soc. Jpn. 2002, 75, 393-413. (d) Hof, F.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2002, 41, 1488-1508. (e) Jasat, A.; Sherman, J. C. Chem. Rev. 1999, 99, 931-967. (f) Russel-Seidel, S.; Stang, P. J. Acc. Chem. Res. 2002, 35, 972-983.
13. For reviews on molecular containers, see: (a) Conn, M. M.; Rebek, J., Jr. Chem, Rev. 1997, 97, 1647-1668. (b) MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. 1999, 38, 1018-1033. (c) Rudkevich, D. M. Bull Chem. Soc. Jpn. 2002, 75, 393-413. (d) Hof, F.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2002, 41, 1488-1508. (e) Jasat, A.; Sherman, J. C. Chem. Rev. 1999, 99, 931-967. (f) Russel-Seidel, S.; Stang, P. J. Acc. Chem. Res. 2002, 35, 972-983.
14. (a) Cram, D. J.; Tanner, M. E.; Thomas, R. Angew. Chem., Int. Ed. Engl. 1991, 30, 1024-1027.
15. (b) Körner, S. K.; Tucci, F. C.; Rudkevich, D. M.; Heinz, T. Chem.-Eur. J. 2000, 6, 187-195.
16. (c) Chen, J.; Körner, S.; Craig, S. L.; Rudkevich, D. M.; Rebek, J., Jr. Nature 2002, 415, 385-386.
17. (d) Kusukawa, T.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 1397-1398.
18. (e) Yoshizawa, M.; Kusukawa, T.; Fujita, M.; Yamaguchi, K. J. Am. Chem. Soc. 2000, 122, 6311-6312.
19. (f) Warmuth, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1347-1350.
20. (g) Warmuth, R. Chem. Commun, 1998, 59-60.
21. (a) Warmuth, R. J. Inclusion Phenom. Macrocyclic Chem. 2000, 37, 1-37.
22. (b) Kang, J.; Rebek, J., Jr. Nature 1997, 385, 50-52.
23. (c) Kang, J.; Santamaria, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389-7390.
24. (d) Kang, J.; Hilmersson, G.; Santamaria, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3650-3656.
25. (e) Yoshizawa, M.; Takeyama, Y.; Kusukawa, T.; Fujita, M. Angew. Chem., Int. Ed. 2002, 41, 1347-1349.
26. (f) Yoshizawa, M.; Takeyama, Y.; Okano, T.; Fujita, M. J. Am. Chem. Soc. 2003, 125, 3243-3247.
27. (g) Makeiff, D. A.; Vishnumurthy, K.; Sherman, J. C. J. Am. Chem. Soc. 2003, 125, 9558-9559 .
28. (h) Kusukawa, T.; Yoshizawa, M.; Fujita, M. Angew. Chem., Int. Ed. 2001, 40, 1879-1884.
29. (a) Yamanaka, M.; Shivanyuk, A.; Rebek, J., Jr. J. Am. Chem. Soc. 2004, 126, 2939-2943.
30. (b) Rebek, J., Jr. Acc. Chem. Res. 1999, 32, 278-286.
31. (c) Rebek, J., Jr. Chem. Soc. Rev. 1996, 25, 255-264.
32. (d) Rebek, J., Jr. Chem. Commun. 2000, 637-643.
33. (e) Rebek, J., Jr. Acc. Chem. Res., 1999, 32, 278-286.
34. (f) MacGillivray, L. R.; Atwood, J. L. Nature 1997, 389, 469-472.
35. (g) Kerchoffs, J. M. C. A.; van Leeuven, F. W. R.; Spek A. L.; Kooijman, H.; Crego-Calama, M.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2003, 42, 5717-5722.
36. (h) Sansone, F.; Baldini, L.; Casnati, A.; Chierici, E.; Faimani, G.; Ugozzoli, F.; Ungaro, R. J. Am. Chem. Soc. 2004, 126, 6205-6206.
37. (i) Rincón, A. M.; Prados, P.; de Mendoza, J. J. Am. Chem. Soc. 2001, 123, 3493-3498.
38. (j) Kobayashi, K.; Ishii, I.; Sakamoto, S.; Shirasake, T.; Yamaguchi, K. J. Am. Chem. Soc. 2003, 125, 10615-10624.
39. (a) Kryschenko, Y. K.; Seidel, S. R.; Muddiman, D. C.; Nepomuceno, A. I.; Stang, P. J. J. Am. Chem. Soc. 2003, 125, 9647-9652.
40. (b) Fujita, M.; Umemoto, K.; Yoshizawa, M.; Fujita, N.; Kusukawa, T.; Biradha, K. Chem. Commun. 2001, 509-518.
41. (c) Takeda, N.; Umemoto, K.; Yamaguchi, K.; Fujita, M. Nature 1999, 398, 794-796.
42. (d) Jacopozzi, P.; Dalcanale, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 613-615.
43. (e) Radhakrishnan, U.; Schweiger, M.; Stang, P. J. Org. Lett. 2001, 3, 3141-3143.
44. (f) Leung, D. H.; Fiedler, D.; Bergman, R. G.; Raymond, K. N. Angew. Chem., Int. Ed. 2004, 43, 963-966.
45. (g) Fox, O. D.; Leung, J. F. Y.; Hunter, J. M.; Dalley, N. K.; Harrison, R. G. Inorg. Chem. 2000, 39, 783-790.
46. (a) Zadmard, R.; Schrader, T.; Grawe, T.; Kraft, A. Org. Lett. 2002, 4, 1687-1690.
47. (b) Zadmard, R.; Junkers, M.; Schrader, T.; Grawe, T.; Kraft, A J. Org. Chen 2003, 68, 6511-6521.
48. (c) Fiammengo, R.; Timmerman, P.; de Jong, F.; Reinhoudt, D. N. Chem. Commun. 2000, 2313-2314.
49. (d) Grawe, T.; Schrader, T.; Gurrath, M.; Kraft, A.; Osterod, F. Org. Lett. 2000, 2, 29-32.
50. (e) Corbellini, F.; Fiammengo, R.; Timmerman, P.; Crego-Calama, M.; Versluis, K.; Heck, A. J. R.; Luyten, I.; Reinhoudt, D. N. J. Am. Chem. Soc. 2002, 124, 6569-6575.
51. (a) Swalen, J. D.; Allara, D. L.; Andrade, J. D.; Chandross, E. A.; Garoff, S.; Israelachvili, J.; MacCarthy, T. J.; Murray, R.; Pease, R. F.; Rabolt, J. F.; Wynn, K. J.; Yu, H. Langmuir 1987, 3, 932-950.
52. (b) Mrksich, M.; Whitesides, G. M. Trends Biotechnol. 1995, 13, 228-235.
53. (c) Shipway, A. N.; Katz, E.; Willner, I. Chem. Phys. Chem. 2000, 1, 18-52.
54. (d) Willner, I.; Katz, E. Angew. Chem., Int. Ed. 2000, 39, 1180-1218.
55. (e) Leech, D. Chem. Soc. Rev. 1994, 23, 205-213.
56. (f) Granick, S.; Kumar, S. K.; Amis, E. J.; Antonietti, M.; Balazs, A. C.; Chakraborty, A. K.; Grest, G. S.; Hawker, C.; Janmey, P.; Kramer, E. J.; Nuzzo, R.; Russell, T. P.; Safinya, C. R. J. Polym. Sci., Part B: Polym. Phys. 2003, 41, 2755-2793.
57. (g) Matsui, H.; Porrata, P.; Douberly, G. E., Jr. Nano Lett. 2001, 1, 461-464.
58. (h) Ball, P. Nature 2000, 406, 118-120.
59. (i) Chen, J.; Reed, M. A.; Rawlett, A. M.; Tour, J. M. Science 1999, 286, 1550-1552.
60. (j) Gittins, D. I.; Bethell, D.; Schiffrin, D. J.; Nichols, R. J. Nature 2000, 408, 67-69.
61. (k) Fendler, J. H. Chem. Mater. 2001, 13, 3196-3210.
62. (a) Lehn, J.-M. Science 1996, 35, 538-540.
63. (b) Garcia-Lopez, J. J.; Zapotoczny, S.; Timmerman, P.; van Veggel, F. C. J. M.; Vancso, G. J.; Crego-Calama, M.; Reinhoudt, D. N. Chem. Commun. 2003, 352-353.
64. (c) Friggeri, A.; van Manen, H.-J.; Auletta, T.; Li, X.-M.; Zapotoczny, H.; Schönherr, H.; Vancso, G. J.; Huskens, J.; van Veggel, F. C. J. M.; Reinhoudt, D. N. J. Am. Chem. Soc. 2001, 123, 6388-6395.
65. (a) Ulman, A. Chem. Rev. 1996, 96, 1533-1554.
66. (b) Ulman, A. Acc. Chem. Res. 2001, 34, 855-863.
67. (c) Ulman, A. An Introduction to Ultrathin Organic Films; Academic Press: Boston, 1991.
68. (d) Ulman, A. Thin Films; Academic Press: Boston, 1999; Vol. 23.
69. (e) Gupta, P.; Loos, K.; Korniakov, A.; Spagnoli, C.; Cowman, M.; Ulman, A. Angew. Chem., Int. Ed. 2004, 43, 520-523.
70. (a) Dubois, L. H.; Nuzzo, R. G. Annu. Rev. Phys. Chem. 1992, 43, 437-463.
71. (b) Rojas, M. T.; Königer, R.; Stoddart, J. F.; Kaifer, A. E. J. Am. Chem. Soc. 1995, 117, 336-343.
72. (c) Thoden van Velzen, E. U.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Am. Chem. Soc. 1994, 116, 3597-3598.
73. (d) Huisman, B.-H.; Thoden van Velzen, E. U.; van Veggel, F. C. J. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Tetrahedron Lett. 1995, 18, 3273-3276.
74. (e) Nelles, G.; Weisser, M.; Back, R.; Wohlfart, P.; Wenz, P.; Wenz, G.; Mittler-Neher, S. J. Am. Chem. Soc. 1996, 118, 5039-5046.
75. (f) Zhang, S.; Echegoyen, L. Org. Lett. 2004, 6, 791-794.
76. (g) Nissink, J. W. M.; Wink, T.; van der Mass, J. H. J. Mol. Struct. 1999, 479, 65-73.
77. (h) Yang, X.; McBranch, D.; Swanson, B.; Li. D. Angew. Chem., Int. Ed. Engl. 1996, 35, 538-540.
78. (a) Maeda, Y.; Fukuda, T.; Yamamoto, H.; Kitano, H. Langmuir 1997, 13, 4187-4189.
79. (b) Arias, F.; Godinez, L. A.; Wilson, S. R.; Kaifer, A. E.; Echegoyen, L. J. Am. Chem. Soc. 1996, 118, 6086-6087.
80. (c) Sigal, G. B.; Bamdad, C.; Barberis, A.; Strominger, J.; Whitesides, G. M. Anal. Chem. 1996, 68, 490-497.
81. (d) Brown. S. A.; Easton, C. J.; Kelly, J. B. J. Inclusion Phenom. Macrocyclic Chem. 2003, 46, 167-173.
82. (e) Banerjee, I. A.; Yu, L.; Matsui, H. J. J. Am. Chem. Soc. 2003, 125, 9542-9543.
83. (f) Fragoso, A.; Caballero, J.; Almirall, E.; Villalonga, R.; Cao, R. Langmuir 2002, 18, 5051-5054.
84. (g) Beulen, M. W. J.; Bügler, J.; De Jong, M. R.; Lammerink, B.; Huskens, J.; Schönherr, H.; Vancso, G. J.; Boukamp, B. A.; Wieder, H.; Offenhäuser, A.; Knoll, W.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Chem.-Eur. J. 2000, 6, 1176-1183.
85. (a) Hatzor, A.; Moav, T.; Cohen, H.; Matlis, S.; Libman, J.; Vaskevich, A.; Shanzer, A.; Rubinstein, I. J. Am. Chem. Soc. 1998, 120, 13469-13477.
86. (b) Moav, T.; Hatzor, A.; Cohen, H.; Libman, J.; Rubinstein, I.; Shanzer, A. Chem.-Eur. J. 1998, 4, 502-507.
87. (c) Hatzor, A.; Moav, T.; Yochelis, S.; Vaskevich, A.; Shanzer, A.; Rubinstein, I. Langmuir 2000, 16, 4420-4423.
88. (d) Godínez, L. A.; Lin, J.; Muñoz, M.; Coleman, A. W.; Rubin, S.; Parikh, A.; Zawodzinski, T. A., Jr.; Loveday, D.; Ferraris, J. P.; Kaifer, A. E. Langmuir 1998, 14, 137-144.
89. (a) Huisman, B. H.; Rudkevich, D. M.; van Veggel, F. C. J. M.; Reinhoudt, D. N. J. Am. Chem. Soc. 1996, 118, 3523-3524.
90. (b) Huisman, B. H.; Rudkevich, D. M.; Farrán, A.; Verboom, W.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Eur. J. Org. Chem. 2000, 269-274.
91. (a) Levi, S.; Guatteri, P.; van Veggel, F. C. J. M.; Vancso, G. J.; Dalcanale, E.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2001, 40, 1892-1896.
92. (b) Menozzi, E.; Pinalli, R.; Speets, E.; Ravoo B.-J.; Dalcanale, E.; Reinhoudt, D. N. Chem.-Eur. J. 2004, 10, 2199-2206.
93. Corbellini, F.; Di Costanzo, L.; Crego-Calama, M.; Geremia, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2003, 125, 9946-9947.
94. (a) Huskens, J.; Deij, M. A.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2002, 41, 4467-4471.
95. (b) Auletta, T.; Dordi, B.; Mulder, A.; Sartori, A.; Onclin, S.; Bruinink, C. M.; Péter, M.; Nijhuis, C. A.; Beijleveld, H.; Schönherr, H.; Vancso, G. J.; Casnati, A.; Ungaro, R.; Ravoo, B. J.; Huskens, J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2004, 43, 369-373.
96. Fiammengo, R.; Timmerman, P.; Huskens, J.; Versluis, K.; Heck, A. J. R.; Reinhoudt, D. N. Tetrahedron 2002, 58, 757-764.
97. Kim, K. S.; Qian, L. Tetrahedron Lett. 1993, 34, 7677-7680.
98. De Jong, M. R.; Huskens, J.; Reinhoudt, D. N. Chem.-Eur. J. 2001, 7, 4164-4170.
99. Scuck, P. Annu. Rev. Biophys. Biomol. Struct. 1997, 26, 541-566.
100. Mulder, A.; Auletta, T.; Sartori, A.; Casnati, A.; Ungaro, R.; Huskens, J.; Reinhoudt, D. N. J. Am. Chem. Soc. 2004, 126, 6627-6636.
101. Huskens, J.; Mulder, A.; Auletta, T.; Nijhuis, C. A.; Ludden, M. J. W.; Reinhoudt, D. N. J. Am. Chem. Soc. 2004, 126, 6784-6797.
102. Nijhuis, C. A.; Husketis, J.; Reinhoudt, D. N. J. Am. Chem. Soc. 2004, 726, 12266-12267.
103. -1.
104. -1 (see, e.g., Schneider, H.-J.; Yatsimirsky, A. Principles and Methods in Supramolecular Chemistry; Wiley: Chichester, U.K., 2000), which is clearly too high to explain our results.
105. The small drop in the SPR signal upon restoration of the 4 mM β-CD + 10 mM KCl solution is attributed to the change in refractive index. The fact the SPR signal remains elevated with respect to the starting positions rules out desorption of the building block.
106. Lenferink, A. T. M.; Kooyman, R. P. H.; Greve, J. Sens. Act. B 1991, 261-265.