Supramolecular polymers in aqueous medium: Rational design based on directional hydrophobic interactions

Journal of the American Chemical Society

Volumn 133, Issue 40, 2011, Pages 16201-16211

  Ustinov, Alona ^a   Weissman, Haim ^a   Shirman, Elijah ^a   Pinkas, Iddo ^a   Zuo, Xiaobing ^b   Rybtchinski, Boris ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

^b ARGONNE NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS MEDIUM; ASSOCIATION CONSTANT; EXCITON CONFINEMENT; GENERAL APPROACH; HYDROPHOBIC INTERACTIONS; HYDROPHOBIC MOTIFS; MULTIVALENCY; NONCOVALENT ASSEMBLIES; NOVEL STRATEGIES; OPTICAL SPECTROSCOPY; PERYLENE DIIMIDES; PHOTONIC BEHAVIOR; RATIONAL DESIGN; SMALL ANGLE X-RAY SCATTERING; STACKED SYSTEMS; STACKING INTERACTION; STERICS; SUPRAMOLECULAR POLYMERIZATION; SUPRAMOLECULAR POLYMERS;

BENZENE; DESIGN; ELECTRON SPIN RESONANCE SPECTROSCOPY; HYDROGEN BONDS; POLYMERIZATION; POLYMERS; SCAFFOLDS; SELF ASSEMBLY; SUPRAMOLECULAR CHEMISTRY; X RAY SCATTERING;

HYDROPHOBICITY;

BENZENE DERIVATIVE; POLYMER;

ARTICLE; CHEMICAL PHENOMENA; CRYOGENIC ELECTRON MICROSCOPY; ELECTRON SPIN RESONANCE; ENTHALPY; HYDROGEN BOND; HYDROPHOBICITY; MICROSCOPY; MOLECULAR INTERACTION; OPTICAL SPECTROSCOPY; POLYMERIZATION; SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

BENZENE; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; IMIDES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PERYLENE; POLYMERS; WATER;

EID: 80053535138     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2066225     Document Type: Article

References (54)

1. Stupp, S. I.; LeBonheur, V.; Walker, K.; Li, L. S.; Huggins, K. E.; Keser, M.; Amstutz, A. Science 1997, 276, 384-389
2. Lehn, J.-M. Science 2002, 295, 2400-2403
3. Reinhoudt, D. N.; Crego-Calama, M. Science 2002, 295, 2403-2407
4. Stoddart, J. F. Nat. Chem. 2009, 1, 14-15
5. De Greef, T. F. A.; Smulders, M. M. J.; Wolffs, M.; Schenning, A. P. H. J.; Sijbesma, R. P.; Meijer, E. W. Chem. Rev. 2009, 109, 5687-5754
6. Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097
7. Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 271, 1095-1098
8. Castellano, R. K.; Rudkevich, D. M.; Rebek, J. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 7132-7137
9. Rehm, T. H.; Schmuck, C. Chem. Soc. Rev. 2010, 39, 3597-3611
10. Chen, Z.; Lohr, A.; Saha-Moller, C. R.; Würthner, F. Chem. Soc. Rev. 2009, 38, 564-584
11. Harada, A. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 5113-5119
12. Zayed, J. M.; Nouvel, N.; Rauwald, U.; Scherman, O. A. Chem. Soc. Rev. 2010, 39, 2806-2816
13. Besenius, P.; Portale, G.; Bomans, P. H. H.; Janssen, H. M.; Palmans, A. R. A.; Meijer, E. W. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 17888-17893
14. Baram, J.; Shirman, E.; Ben-Shitrit, N.; Ustinov, A.; Weissman, H.; Pinkas, I.; Wolf, S. G.; Rybtchinski, B. J. Am. Chem. Soc. 2008, 130, 14966-14967
15. Neelakandan, P. P.; Pan, Z. Z.; Hariharan, M.; Zheng, Y.; Weissman, H.; Rybtchinski, B.; Lewis, F. D. J. Am. Chem. Soc. 2010, 132, 15808-15813
16. Arnaud, A.; Belleney, J.; Boue, F.; Bouteiller, L.; Carrot, G.; Wintgens, W. Angew. Chem., Int. Ed. 2004, 43, 1718-1721
17. Obert, E.; Bellot, M.; Bouteiller, L.; Andrioletti, F.; Lehen-Ferrenbach, C.; Boue, F. J. Am. Chem. Soc. 2007, 129, 15601-15605
18. Amdursky, N.; Gazit, E.; Rosenman, G. Adv. Mater. 2010, 22, 2311-2315
19. Amdursky, N.; Molotskii, M.; Gazit, E.; Rosenman, G. Appl. Phys. Lett. 2009, 94 261907
20. Buchvarov, I.; Wang, Q.; Raytchev, M.; Trifonov, A.; Fiebig, T. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 4794-4797
21. Giaimo, J. M.; Lockard, J. V.; Sinks, L. E.; Scott, A. M.; Wilson, T. M.; Wasielewski, M. R. J. Phys. Chem. A 2008, 112, 2322-2330
22. Fink, R. F.; Seibt, J.; Engel, V.; Renz, M.; Kaupp, M.; Lochbrunner, S.; Zhao, H. M.; Pfister, J.; Würthner, F.; Engels, B. J. Am. Chem. Soc. 2008, 130, 12858-12859
23. Kilway, K. V.; Siegel, J. S. Tetrahedron 2001, 57, 3615-3627
24. Hennrich, G.; Anslyn, E. V. Chem.-Eur. J. 2002, 8, 2219-2224
25. Gebers, J.; Rolland, D.; Frauenrath, H. Angew. Chem., Int. Ed. 2009, 48, 4480-4483
26. Zhang, X.; Rehm, S.; Safont-Sempere, M. M.; Würthner, F. Nat. Chem. 2009, 1, 623-629
27. Zhang, X.; Chen, Z.; Würthner, F. J. Am. Chem. Soc. 2007, 129, 4886-4887
28. Ryu, J. H.; Jang, C. J.; Yoo, Y. S.; Lim, S. G.; Lee, M. J. Org. Chem. 2005, 70, 8956-8962
29. Golubkov, G.; Weissman, H.; Shirman, E.; Wolf, S. G.; Pinkas, I.; Rybtchinski, B. Angew. Chem., Int. Ed. 2009, 48, 926-930
30. Krieg, E.; Shirman, E.; Weissman, H.; Shimoni, E.; Wolf, S. G.; Pinkas, I.; Rybtchinski, B. J. Am. Chem. Soc. 2009, 131, 14365-14373
31. Mulder, A.; Huskens, J.; Reinhoudt, D. N. Org. Biomol. Chem. 2004, 2, 3409-3424
32. Badjic, J. D.; Nelson, A.; Cantrill, S. J.; Turnbull, W. B.; Stoddart, J. F. Acc. Chem. Res. 2005, 38, 723-732
33. Würthner, F. Chem. Commun. 2004, 1564-1579
34. Ahrens, M. J.; Sinks, L. E.; Rybtchinski, B.; Liu, W.; Jones, B. A.; Giaimo, J. M.; Gusev, A. V.; Goshe, A. J.; Tiede, D. M.; Wasielewski, M. R. J. Am. Chem. Soc. 2004, 126, 8284-8294
35. Cui, H.; Hodgdon, T. K.; Kaler, E. W.; Abezgauz, L.; Danino, D.; Lubovsky, M.; Talmon, Y.; Pochan, D. J. Soft Matter 2007, 3, 945-955
36. Friedrich, H.; Frederik, P. M.; de With, G.; Sommerdijk, N. A. J. M. Angew. Chem., Int. Ed. 2010, 49, 7850-7858
37. Shimizu, T.; Masuda, M.; Minamikawa, H. Chem. Rev. 2005, 105, 1401-1443
38. Wilson, T. M.; Zeidan, T. A.; Hariharan, M.; Lewis, F. D.; Wasielewski, M. R. Angew. Chem., Int. Ed. 2010, 49, 2385-2388
39. Svergun, D. I. Biophys. J. 1999, 76, 2879-2886
40. Svergun, D. I.; Koch, M. H. Rep. Prog. Phys. 2003, 66, 1735-1782
41. Smulders, M. M. J.; Nieuwenhuizen, M. M. L.; de Greef, T. F. A.; van der Schoot, P.; Schenning, A. P. H. J.; Meijer, E. W. Chem.-Eur. J. 2010, 16, 362-367
42. Smulders, M. M. J.; Schenning, A. P. H. J.; Meijer, E. W. J. Am. Chem. Soc. 2008, 130, 606-611
43. Martin, R. B. Chem. Rev. 1996, 96, 3043-3064
44. Zhao, D. H.; Moore, J. S. Org. Biomol. Chem. 2003, 1, 3471-3491
45. Smithrud, D. B.; Wyman, T. B.; Diederich, F. J. Am. Chem. Soc. 1991, 113, 5420-5426
46. Chandler, D. Nature 2005, 437, 640-647
47. Daniel, C.; Herz, L. M.; Silva, C.; Hoeben, F. J. M.; Jonkheijm, P.; Schenning, A. P. H. J.; Meijer, E. W. Phys Rev B 2003, 68 235212
48. Fujitsuka, M.; Okada, A.; Tojo, S.; Takei, F.; Onitsuka, K.; Takahashi, S.; Majima, T. J. Phys. Chem. B 2004, 108, 11935-11941
49. Gilbert, E. E.; Voreck, W. E. Propellants, Explos, Pyrotech. 1989, 14, 19-23 and references therein
50. Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Kluwer Academic/Plenum Publishers: New York, 1999.
51. Petoukhov, M. V.; Konarev, P. V.; Kikhney, A. G.; Svergun, D. I. J. Appl. Crystallogr. 2007, 40, S223-S228
52. Wriggers, W.; Chacon, P. J. Appl. Crystallogr. 2001, 34, 773-776
53. Weissman, H.; Ustinov, A.; Shimoni, E.; Cohen, S. R.; Rybtchinski, B. Polym. Adv. Technol. 2011, 22, 133-138
54. Wallace, K. J.; Hanes, R.; Anslyn, E.; Morey, J.; Kilway, K. V.; Siegel, J. Synthesis 2005, 2080-2083