Three-dimensional shape-persistent fluorescent nanocages: Facile dynamic synthesis, photophysical properties and surface morphologies

Chemistry - A European Journal

Volumn 14, Issue 13, 2008, Pages 3860-3865

  Luo, Jia ^a   Lei, Ting ^a   Xu, Xiaoguang ^a   Li, Fang Mei ^a   Ma, Yuguo ^a   Wu, Kai ^a   Pei, Jian ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

Atomic force microscopy; Cage compounds; Host guest systems; Nanostructures; NMR spectroscopy

Indexed keywords

FLUORESCENCE; LIGHT EMISSION; LUMINESCENCE; SURFACE MORPHOLOGY; SURFACE PROPERTIES;

ATOMIC FORCE MICROSCOPY; CAGE COMPOUNDS; HOST-GUEST SYSTEMS; NANOSTRUCTURES; NMR SPECTROSCOPY;

THREE DIMENSIONAL;

FURAN DERIVATIVE; NANOMATERIAL;

ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMICAL STRUCTURE; CHEMISTRY; FACILE; FLUORESCENCE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; SPECTROPHOTOMETRY; SURFACE PROPERTY; SYNTHESIS; THREE DIMENSIONAL IMAGING; ULTRASTRUCTURE;

FLUORESCENCE; FURANS; IMAGING, THREE-DIMENSIONAL; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MICROSCOPY, ATOMIC FORCE; MOLECULAR STRUCTURE; NANOSTRUCTURES; PHOTOCHEMISTRY; SPECTROPHOTOMETRY; SURFACE PROPERTIES;

EID: 53249091416     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800154     Document Type: Article

References (51)

1. a) S. R. Seidel, P. J. Stang. Acc. Chem. Res. 2002, 35, 972-983;
2. b) S. Höger, Chem. Eur. J. 2004, 10, 1320-1329;
3. c) M. Fujita, M. Tominaga, A. Hori, B. Therrien, Acc. Chem. Res. 2005, 38, 371-380;
4. d) W. Zhang, J. S. Moore, Angew. Chem. 2006, 118, 4524-4548;
5. Angew. Chem. Int. Ed. 2006, 45, 4416-4439.
6. a) T. Heinz, D. M. Rudkevich, J. Rebek, Jr., Nature 1998, 394, 764-766;
7. b) G. W. Orr, L. J. Barbour, J. L. Alwood, Science 1999, 255, 1049-1051;
8. c) J. L. Atwood, L. J. Barbour, A. Jerga. Science 2002, 296, 2367-2369;
9. d) J. L. Atwood, L. J. Barbour, A. Jerga, B. L. Schotlel, Science 2002, 295, 1000-1002;
10. e) M. Yoshizawa, M. Tamura, M. Fujita, J. Anu Chem. Soc. 2004, 126, 6846-6847;
11. f) A. Lützen, Angew. Chem. 2005, 117, 1022-1025;
12. Angew. Chem. Int. Ed. 2005, 44, 1000-1002;
13. g) S. J. Dalgarno, S. A. Tucker, D. B. Bassil, J. L. Atwood, Science 2005, 309, 2037-2039;
14. h) M. Yoshizawa, M. Tamura, M. Fujita, Science 2006, 312, 251-254;
15. i) G. V. Oshovsky, D. N. Reinhoudt, W. Verboom, Angew. Chem. 2007, 119, 2418-2445;
16. Angew. Chem. Int. Ed. 2007, 46, 2366-2393;
17. j) M. D. Pluth, R. G. Bergman, K. N. Raymond, Science 2007, 316, 85-88;
18. k) C. Schmuck, Angew. Chem. 2007, 119, 5932-5935;
19. Angew. Chem. Int. Ed. 2007, 46, 5830-5833;
20. l) R. J. Hooley, H. J. van Anda, J. Rebek, Jr., J. Am. Chem. Soc. 2007, 129, 13464-13473.
21. For cage-like molecules formed via hydrogen bonding, see a) C. T. Seto, G. M. Whitesides, J. Am. Chem. Soc. 1993, 115, 905-916;
22. b) A. Arduini, L. Domiano, L. Ogliosi, A. Pochini, A. Secchi, R. Ungaro, J. Org. Chem. 1997, 62, 7866-7868;
23. c) T. Martin, U. Obst, J. Rebek, Jr., Science 1998, 281, 1842-1845;
24. d) T. Heinz, D. M. Rudkevich, J. Rebek, Jr., Nature 1998, 394, 764-766;
25. e) T. Grawe, T. Schrader, R. Zadmard, A. Kraft, J. Org. Chem. 2002, 67, 3755-3763;
26. f) J. M. C. A. Kerckhoffs, F. W. B. van Leeuwen, A. L. Spek, H. Kooijman, M. Crego-Calama, D. N. Reinhoudt, Angew. Chem. 2003, 115, 5895-5900;
27. Angew. Chem. Int. Ed. 2003, 42, 5717-5722: for cage-like molecules formed via metal coordination,
28. see g) L. Baldini, P. Ballester, A. Casnati, R. M. Gomila, C. A. Hunter, F. Sansone, R. Ungaro, J. Am. Chem. Soc. 2003, 125, 14181-14189;
29. h) E. Menozzi, R. Pinalli, E. A. Speets, B. J. Ravoo, E. Dalcanale, D. N. Reinhoudt, Chem. Eur. J. 2004, 10, 2199-2206;
30. i) R. Pinalli, V. Cristini, V. Sottili, S. Geremia, M. Campagnolo, A. Caneschi, E. Dalcanale, J. Am. Chem. Soc. 2004, 126, 6516-6517;
31. j) S. Sato, J. Iida, K. Suzuki, M. Kawano, T. Ozeki, M. Fujita, Science 2006, 313, 1273-1276;
32. k) Q.-H. Yuan, L.-J. Wan, H. Jude, P. J. Stang, J. Am. Chem. Soc. 2005, 127, 16279-16286;
33. l) P. Ballester, A. I. Oliva, A. Costa, P. M. Deya, A. Frontera, R. M. Gomila, C. A. Hunter, J. Am. Chem. Soc. 2006, 125, 5560-5569;
34. m) M. Yamanaka, Y. Yamada, Y. Sei, K. Yamaguchi, K. Kobayashi, J. Am. Chem. Soc. 2006, 128, 1531-1539;
35. n) K. Harano, S. Hiraoka, M. Shionoya, J. Am. Chem. Soc. 2007, 129, 5300-5301.
36. a) J. D. Badjic, S. J. Cantrill, R. H. Grubbs, E. N. Guidry, R. Orenes, J. F. Stoddart, Angew. Chem. 2004, 116, 3335-3340;
37. Angew. Chem. Int. Ed. 2004, 43, 3273-3278;
38. b) J. D. Badjic, A. Nelson, S. J. Cantrill, W. B. Tumbull, J. F. Stoddart, Acc. Chem. Res. 2005, 38, 723-732.
39. J. Luo, Y. Zhou, Z.-Q. Niu, Q.-F. Zhou, Y. Ma, J. Pei, J. Am. Chem. Soc. 2001, 129, 11314-11315.
40. For dynamic covalent chemistry, see a) S. Ro, S. J. Rowan, A. R. Pease, D. J. Cram, J. F. Stoddart, Org. Lett. 2000, 2, 2411-2414;
41. b) S. J. Rowan, S. J. Cantrill, G. R. L. Cousins, J. K. M. Sanders, J. F. Stoddart, Angew. Chem. 2002, 114, 938-993;
42. Angew. Chem. Int. Ed. 2002, 41, 898-952;
43. c) K. S. Chichak. S. J. Cantrill, A. R. Pease, S-H. Chiu, G. W. V. Cave, J. L. Atwood, J. F. Stoddart. Science 2004, 304, 1308-1312;
44. d) K. C.-F. Leung, F. Arico, S. J. Cantrill, J. F. Stoddart, J. Am. Chem. Soc. 2005, 127, 5808-5810;
45. e) B. H. Northrop, F. Arico, N. Tangchiavang, J. D. Badjic, J. F. Stoddart, Org. Lett. 2006, 5, 3899-3902;
46. f) X. Liu, R. Warmuth, J. Am. Chem. Soc. 2006, 125, 14120-14127;
47. g) C. S. Hartley, E. L. Elliott, J. S. Moore, J. Am. Chem. Soc. 2007, 129, 4512-4513;
48. h) C. S. Hartley, J. S. Moore, J. Am. Chem. Soc. 2007, 129, 11682-11683.
49. T. Grawe, T. Schrader, R. Zadmard, A. Kraft, J. Org. Chem. 2002, 67, 3755-3763.
50. a was shielded by the capping benzene in cage. More details are shown in the Supporting Information.
51. J. Salbeck, N. Yu, J. Bauer, F. Weissortel, H. Bestgen, Synth. Met. 1997, 91, 209-215.