Stereochemistry in subcomponent self-assembly

Accounts of Chemical Research

Volumn 47, Issue 7, 2014, Pages 2063-2073

  Castilla, Ana M ^a   Ramsay, William J ^a   Nitschke, Jonathan R ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84904438952     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar5000924     Document Type: Article

References (55)

1. Nitschke, J. R. Construction, Substitution, and Sorting of Metallo-organic Structures via Subcomponent Self-Assembly Acc. Chem. Res. 2007, 40, 103-112
2. de Hatten, X.; Asil, D.; Friend, R. H.; Nitschke, J. R. Aqueous Self-Assembly of an Electroluminescent Double-Helical Metallopolymer J. Am. Chem. Soc. 2012, 134, 19170-19178
3. Meyer, C. D.; Joiner, C. S.; Stoddart, J. F. Template-Directed Synthesis Employing Reversible Imine Bond Formation Chem. Soc. Rev. 2007, 36, 1705-1723
4. Ronson, T. K.; Zarra, S.; Black, S. P.; Nitschke, J. R. Metal-Organic Container Molecules through Subcomponent Self-Assembly Chem. Commun. 2013, 49, 2476-2490
5. Hubin, T. J.; Busch, D. H. Template Routes to Interlocked Molecular Structures and Orderly Molecular Entanglements Coord. Chem. Rev. 2000, 200-202, 5-52
6. Hannon, M. J.; Painting, C. L.; Jackson, A.; Hamblin, J.; Errington, W. An Inexpensive Approach to Supramolecular Architecture Chem. Commun. 1997, 1807-1808
7. Belowich, M. E.; Stoddart, J. F. Dynamic Imine Chemistry Chem. Soc. Rev. 2012, 41, 2003-2024
8. Howson, S. E.; Bolhuis, A.; Brabec, V.; Clarkson, G. J.; Malina, J.; Rodger, A.; Scott, P. Optically Pure, Water-Stable Metallo-Helical 'Flexicate' Assemblies with Antibiotic Activity Nat. Chem. 2012, 4, 31-36
9. Young, M. C.; Johnson, A. M.; Gamboa, A. S.; Hooley, R. J. Achiral Endohedral Functionality Provides Stereochemical Control in Fe(II)-Based Self-Assemblies Chem. Commun. 2013, 49, 1627-1629
10. 6 Clusters from a New Rigid Ligand J. Chem. Soc., Dalton Trans. 2002, 134-135
11. Ayme, J.-F.; Beves, J. E.; Leigh, D. A.; McBurney, R. T.; Rissanen, K.; Schultz, D. Pentameric Circular Iron(II) Double Helicates and a Molecular Pentafoil Knot J. Am. Chem. Soc. 2012, 134, 9488-9497
12. Pentecost, C. D.; Peters, A. J.; Chichak, K. S.; Cave, G. W. V.; Cantrill, S. J.; Stoddart, J. F. Chiral Borromeates Angew. Chem., Int. Ed. 2006, 45, 4099-4104
13. Knof, U.; von Zelewsky, A. Predetermined Chirality at Metal Centers Angew. Chem., Int. Ed. 1999, 38, 302-322
14. Pfeiffer, P.; Quehl, K. Aktivierung von Komplexsalzen in wäßriger Lösung (II. Mitteil.) Chem. Ber. 1932, 65, 560-565
15. Zhao, C.; Sun, Q.-F.; Hart-Cooper, W. M.; DiPasquale, A. G.; Toste, F. D.; Bergman, R. G.; Raymond, K. N. Chiral Amide Directed Assembly of a Diastereo- and Enantiopure Supramolecular Host and its Application to Enantioselective Catalysis of Neutral Substrates J. Am. Chem. Soc. 2013, 135, 18802-18805
16. Hutin, M.; Nitschke, J. Solvent-Tunable Inversion of Chirality Transfer from Carbon to Copper Chem. Commun. 2006, 1724-1726
17. 3 Chelates Chem. Commun. 2009, 1727-1729
18. 3n+ (M = Mn, Fe, Co, Ni and Zn) Dalton. Trans. 2011, 40, 10416-10433
19. Hutin, M.; Cramer, C. J.; Gagliardi, L.; Shahi, A. R. M.; Bernardinelli, G.; Cerny, R.; Nitschke, J. R. Self-Sorting Chiral Subcomponent Rearrangement During Crystallization J. Am. Chem. Soc. 2007, 129, 8774-8780
20. 6 Cages Angew. Chem., Int. Ed. 2012, 51, 1464-1468
21. 6 Cages J. Am. Chem. Soc. 2012, 134, 15528-15537
22. 4 Tetrahedral Capsule J. Am. Chem. Soc. 2013, 135, 17999-18006
23. Bonner, W. A. Parity Violation and the Evolution of Biomolecular Homochirality Chirality 2000, 12, 114-126
24. Feringa, B. L.; van Delden, R. A. Absolute Asymmetric Synthesis: The Origin, Control, and Amplification of Chirality Angew. Chem., Int. Ed. 1999, 38, 3418-3438
25. Kaminker, R.; de Hatten, X.; Lahav, M.; Lupo, F.; Gulino, A.; Evmenenko, G.; Dutta, P.; Browne, C.; Nitschke, J. R.; van der Boom, M. E. Assembly of Surface-Confined Homochiral Helicates: Chiral Discrimination of DOPA and Unidirectional Charge Transfer J. Am. Chem. Soc. 2013, 135, 17052-17059
26. Liu, T.; Liu, Y.; Xuan, W.; Cui, Y. Chiral Nanoscale Metal-Organic Tetrahedral Cages: Diastereoselective Self-Assembly and Enantioselective Separation Angew. Chem., Int. Ed. 2010, 49, 4121-4124
27. Nishioka, Y.; Yamaguchi, T.; Kawano, M.; Fujita, M. Asymmetric [2 + 2] Olefin Cross Photoaddition in a Self-Assembled Host with Remote Chiral Auxiliaries J. Am. Chem. Soc. 2008, 130, 8160-8161
28. Xuan, W.; Zhang, M.; Liu, Y.; Chen, Z.; Cui, Y. A Chiral Quadruple-Stranded Helicate Cage for Enantioselective Recognition and Separation J. Am. Chem. Soc. 2012, 134, 6904-6907
29. Ziegler, M.; Davis, A. V.; Johnson, D. W.; Raymond, K. N. Structural Memory Angew. Chem., Int. Ed. 2003, 42, 665-668
30. 6 Cage Complex Chem. Commun. 2005, 4647-4649
31. Stang, P. J.; Olenyuk, B.; Muddiman, D. C.; Smith, R. D. Transition-Metal-Mediated Rational Design and Self-Assembly of Chiral, Nanoscale Supramolecular Polyhedra with Unique T Symmetry Organometallics 1997, 16, 3094-3096
32. Castilla, A. M.; Ramsay, W. J.; Nitschke, J. Stereochemical Communication within Tetrahedral Capsules Chem. Lett. 2014, 43, 256-263
33. Hamilton, T. D.; MacGillivray, L. R. Enclosed Chiral Environments from Self-Assembled Metal-Organic Polyhedra Cryst. Growth Des. 2004, 4, 419-430
34. Prins, L. J.; Verhage, J. J.; Jong, F. D.; Timmerman, P.; Reinhoudt, D. N. Enantioselective Noncovalent Synthesis of Hydrogen-Bonded Chem.-Eur. J. 2002, 2302-2313
35. Yashima, E.; Maeda, K.; Okamoto, Y. Memory of Macromolecular Helicity Assisted by Interaction with Achiral Small Molecules Nature 1999, 449-451
36. Delsuc, N.; Hutin, M.; Campbell, V. E.; Kauffmann, B.; Nitschke, J. R.; Huc, I. Metal-Directed Dynamic Formation of Tertiary Structure in Foldamer Assemblies: Orienting Helices at an Angle Chem.-Eur. J. 2008, 14, 7140-7143
37. 8+ Capsules J. Am. Chem. Soc. 2011, 134, 5110-5119
38. Sørensen, A.; Castilla, A. M.; Ronson, T. K.; Pittelkow, M.; Nitschke, J. R. Chemical Signals Turn On Guest Binding through Structural Reconfiguration of Triangular Helicates Angew. Chem., Int. Ed. 2013, 52, 11273-11277
39. 6 Cages J. Am. Chem. Soc. 2011, 133, 13652-13660
40. 6 Cage Complexes Proc. Natl. Acad. Sci. U.S.A. 2013, 110, 10531-10535
41. 6 Cubic Cage that Selectively Encapsulates Large Aromatic Guests Angew. Chem., Int. Ed. 2011, 50, 3479-3483
42. 24 Cubic Cage Angew. Chem., Int. Ed. 2012, 51, 6681-6685
43. Ramsay, W. J.; Ronson, T. K.; Clegg, J. K.; Nitschke, J. R. Bidirectional Regulation of Halide Binding in a Heterometallic Supramolecular Cube Angew. Chem., Int. Ed. 2013, 52, 13439-13443
44. 12 Cubic Capsule Angew. Chem., Int. Ed. 2013, 52, 1944-1948
45. 1H NMR Spectroscopy Chem.-Eur. J. 2002, 8, 2679-2683
46. Nitschke, J. R.; Hutin, M.; Bernardinelli, G. The Hydrophobic Effect as a Driving Force in the Self-Assembly of a [2 × 2] Copper(I) Grid Angew. Chem., Int. Ed. 2004, 43, 6724-6727
47. 4 Tube Angew. Chem., Int. Ed. 2012, 51, 1881-1884
48. Najar, A. M.; Tidmarsh, I. S.; Adams, H.; Ward, M. D. Cubes, Squares, and Books: A Simple Transition Metal/Bridging Ligand Combination Can Lead to a Surprising Range of Structural Types with the Same Metal/Ligand Proportions Inorg. Chem. 2009, 48, 11871-11881
49. Ward, M. D. Polynuclear Coordination Cages Chem. Commun. 2009, 4487-4499
50. 15 Pentagonal Prism Nat. Chem. 2012, 4, 751-756
51. Riddell, I. A.; Hristova, Y. R.; Clegg, J. K.; Wood, C. S.; Breiner, B.; Nitschke, J. R. Five Discrete Multinuclear Metal-Organic Assemblies from One Ligand: Deciphering the Effects of Different Templates J. Am. Chem. Soc. 2013, 135, 2723-2733
52. Meng, W.; Ronson, T. K.; Clegg, J. K.; Nitschke, J. R. Transformations within a Network of Cadmium Architectures Angew. Chem., Int. Ed. 2013, 52, 1017-1021
53. 18 Coordination Cages by Subcomponent Self-Assembly Inorg. Chem. 2013, 52, 5648-5650
54. 15 Prism Angew. Chem., Int. Ed. 2013, 52, 4837-4840
55. 12] Capsule with an Icosahedral Framework Angew. Chem., Int. Ed. 2013, 52, 9027-9030