Iptycene-derived crown ether hosts for molecular recognition and self-assembly

Accounts of Chemical Research

Volumn 47, Issue 7, 2014, Pages 2026-2040

  Han, Ying ^a   Meng, Zheng ^a   Ma, Ying Xian ^a   Chen, Chuan Feng ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84904438277     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar5000677     Document Type: Article

References (57)

1. Pedersen, C. J. Cyclic polyethers and their complexes with metal salts J. Am. Chem. Soc. 1967, 89, 2495-2496
2. Cram, D. J.; Cram, J. M. Host-guest chemistry Science 1974, 183, 803-809
3. Gokel, G. W.; Leevy, W. M.; Weber, M. E. Crown ethers: Sensors for ions and molecular scaffolds for materials and biological models Chem. Rev. 2004, 104, 2723-2750
4. Kang, S. O.; Llinares, J. M.; Dayc, V. W.; Bowman-Jamesc, K. Cryptand-like anion receptors Chem. Soc. Rev. 2010, 39, 3980-4003
5. Guo, D. S.; Liu, Y. Calixarene-based supramolecular polymerization in solution Chem. Soc. Rev. 2012, 41, 5907-5921
6. Isaacs, L. Cucurbit[ n ]urils: From mechanism to structure and function Chem. Commun. 2009, 619-629
7. Xue, M.; Yang, Y.; Chi, X. D.; Zhang, Z. B.; Huang, F. H. Pillararenes, a new class of macrocycles for supramolecular chemistry Acc. Chem. Res. 2012, 45, 1294-1308
8. Gloe, K., Ed. Macrocyclic Chemistry: Current Trends and Future Perspectives; Springer: Dordrecht, The Netherlands, 2005.
9. Wang, M.-X. Nitrogen and oxygen bridged calixaromatics: Synthesis, structure, functionalization, and molecular recognition Acc. Chem. Res. 2012, 45, 182-195
10. Rambo, B. M.; Gong, H. Y.; Oh, M.; Sessler, J. L. The "Texas-sized" molecular box: A versatile building block for the construction of anion-directed mechanically interlocked structures Acc. Chem. Res. 2012, 45, 1390-1401
11. Allwood, B. L.; Shahriarizavareh, H.; Stoddart, J. F.; Williams, D. J. Complexation of paraquat and diquat by a bismetaphenylene-32-crown-10 derivative J. Chem. Soc., Chem. Commun. 1987, 1058-1061
12. Ashton, P. R.; Campbell, P. J.; Chrystal, E. J. T.; Peter, T. G.; Menzer, S.; Phlip, D.; Sepencer, N.; Stoddart, J. F.; Tasher, P. A.; Willams, D. J. Dialkylammonium ion/crown ether complexes: The forerunners of a new family of interlocked molecules Angew. Chem., Int. Ed. 1995, 34, 1865-1869
13. Bryant, W. S.; Jones, J. W.; Mason, P. E.; Guzei, I.; Rheingold, A. L.; Fronczek, F. R.; Nagvekar, D. S.; Gibson, H. W. A new cryptand: Synthesis and complexation with paraquat Org. Lett. 1999, 1, 1001-1004
14. Zhang, M.; Zhu, K.; Huang, F. H. Improved complexation of paraquat derivatives by the formation of crown ether-based cryptands Chem. Commun. 2010, 46, 8131-8141
15. +-templated formation of [2]pseudorotaxanes exhibiting significant optical outputs Angew. Chem., Int. Ed. 2007, 46, 2013-2017
16. Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Venturi, M. Artificial molecular-level machines: Which energy to make them work? Acc. Chem. Res. 2001, 34, 445-455
17. Loeb, S. J. Rotaxanes as ligands: From molecules to materials Chem. Soc. Rev. 2007, 36, 226-235
18. Badjić, J. D.; Nelson, A.; Cantrill, S. J.; Turnbull, W. B.; Stoddart, J. F. Multivalency and cooperativity in supramolecular chemistry Acc. Chem. Res. 2005, 38, 723-732
19. Chong, J. H.; MacLachlan, M. J. Iptycenes in supramolecular and materials chemistry Chem. Soc. Rev. 2009, 38, 3301-3315
20. Yang, J. S.; Yan, J. L. Central-ring functionalization and application of the rigid, aromatic, and H-shaped pentiptycene scaffold Chem. Commun. 2008, 1501-1512
21. Chen, C.-F. Novel triptycene-derived hosts: Synthesis and their applications in supramolecular chemistry Chem. Commun. 2011, 47, 1674-1688
22. Zong, Q.-S.; Chen, C.-F. Novel triptycene-based cylindrical macrotricyclic host: Synthesis and complexation with paraquat derivatives Org. Lett. 2006, 8, 211-214
23. 2+ selective fluorescence probe J. Org. Chem. 2010, 75, 5092-5098
24. +-ion- controlled binding and release of the guests in the complexes J. Org. Chem. 2012, 77, 2422-2430
25. Han, T.; Chen, C.-F. Selective template complexation of a cylindrical macrotricyclic host with neutral guests: Three cation-controlled switchable processes J. Org. Chem. 2007, 72, 7287-7293
26. Li, J.; Guo, J.-B.; Yang, G.; Zhang, G.-X.; Chen, C.-F.; Zhang, D.-Q. Inclusion of tetrachloroquinone and metal ions in a macrotricyclic molecule with a tetrathiafulvalene moiety prompts intermolecular electron transfer Asian J. Org. Chem. 2012, 1, 166-172
27. Guo, J.-B.; Xiang, J.-F.; Chen, C.-F. Synthesis of a bis-macrotricyclic host and its complexation with secondary ammonium salts: An acid-base switchable molecular handcuff Eur. J. Org. Chem. 2010, 5056-5062
28. Han, T.; Chen, C.-F. A triptycene-based bis(crown ether) host: Complexation with both paraquat derivatives and dibenzylammonium salts Org. Lett. 2006, 8, 1069-1072
29. Peng, X.-X.; Lu, H.-Y.; Han, T.; Chen, C.-F. Synthesis of a novel triptycene-based molecular tweezers and its complexation with paraquat derivatives Org. Lett. 2007, 9, 895-898
30. Jiang, Y.; Cao, Y.; Zhao, J.-M.; Xiang, J.-F.; Chen, C.-F. Synthesis of a triptycene-derived bisparaphenylene-34-crown-10 and its complexation with both paraquat and cyclobis(paraquat- p -phenylene) J. Org. Chem. 2010, 75, 1767-1770
31. Cao, J.; Lu, H.-Y.; Chen, C.-F. Synthesis, structures, and properties of peripheral o -dimethoxy-substituted pentiptycene quinones and their o -quinone derivatives Tetrahedron 2009, 65, 8104-8112
32. Cao, J.; Lu, H.-Y.; You, X.-J.; Zheng, Q.-Y.; Chen, C.-F. Complexation of a pentiptycene-based tweezers-like receptor with paraquat derivatives: Ion-controlled binding and release of guests Org. Lett. 2009, 11, 4446-4449
33. Cao, J.; Jiang, Y.; Zhao, J.-M.; Chen, C.-F. A pentiptycene-based bis(crown ether) host: synthesis and its complexation with cyclobis(paraquat- p -phenylene) Chem. Commun. 2009, 1987-1989
34. 4+ in host-guest systems J. Org. Chem. 2011, 76, 1644-1652
35. Zhu, X.-Z.; Chen, C.-F. A highly efficient approach to [4]pseudocatenanes by threefold metathesis reactions of a triptycene-based tris[2]pseudorotaxane J. Am. Chem. Soc. 2005, 127, 13158-13159
36. Zhu, X.-Z.; Chen, C.-F. Efficient synthesis of a chiral [4]pseudocatenane and its derivatives: A novel ship's wheel-like interlocked structure Chem.-Eur. J. 2006, 12, 5603-5609
37. Zhao, J.-M.; Zong, Q.-S.; Han, T.; Xiang, J.-F.; Chen, C.-F. Guest-dependent complexation of triptycene-based macrotricyclic host with paraquat derivatives and secondary ammonium salts: A chemically controlled complexation process J. Org. Chem. 2008, 73, 6800-6806
38. Han, Y.; Cao, J.; Li, P.-F.; Zong, Q.-S.; Zhao, J.-M.; Guo, J.-B.; Xiang, J.-F.; Chen, C.-F. Complexation of triptycene-derived macrotricyclic polyether with paraquat derivatives, diquat, and a 2,7-diazapyrenium salts: Guest-induced conformational changes of the host J. Org. Chem. 2013, 78, 3235-3242
39. - and bipyridinium rings in the solid state Org. Lett. 2011, 13, 5688-5691
40. Ma, Y.-X.; Han, Y.; Cao, J.; Chen, C.-F. Complexation of a pentiptycene-derived trans -bis(crown ether) host with different terminally functionalized paraquat derivatives in solution and the solid state: A switchable complexation process controlled by potassium ions Org. Biomol. Chem. 2013, 11, 8183-8190
41. Han, T.; Zong, Q.-S.; Chen, C.-F. Complexation of triptycene-based cylindrical macrotricyclic polyether toward diquaternary salts: Ion-controlled binding and release of the guests J. Org. Chem. 2007, 72, 3108-3111
42. Han, T.; Chen, C.-F. Formation of ternary complexes between a macrotricyclic host and hetero-guest pairs: An acid-base controlled selective complexation process Org. Lett. 2007, 9, 4207-4210
43. Han, Y.; Gu, Y.-K.; Xiang, J.-F.; Chen, C.-F. Complexation between triptycene-based macrotricyclic host and π-extended viologens: Formation of supramolecular poly[3]pseudorotaxanes Chem. Commun. 2012, 48, 11076-11078
44. Zong, Q.-S.; Zhang, C.; Chen, C.-F. Self-assembly of triptycene-based cylindrical macrotricyclic host with dibenzylammonium ions: Construction of dendritic [3]pseudorotaxanes Org. Lett. 2006, 8, 1859-1862
45. Jiang, Y.; Zhu, X.-Z.; Chen, C.-F. Multivalency-directed magic-ring [2](3)catenane by olefin metathesis Chem.-Eur. J. 2010, 16, 14285-14289
46. Odell, B.; Reddinggton, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. Cyclobis(paraquat- p -phenylene): A tetracationic multipurpose receptor Angew. Chem., Int. Ed. Engl. 1988, 27, 1547-1550
47. Cao, J.; Lu, H.-Y.; Xiang, J.-F.; Chen, C.-F. Complexation between pentiptycene-based mono(crown ether)s and tetracationic cyclobis(paraquat-p- phenylene): Who is the host or the guest? Chem. Commun. 2010, 46, 3586-3588
48. Han, Y.; Guo, J.-B.; Cao, J.; Chen, C.-F. Ion-controlled switchable complexation between pentiptycene-based tweezers-like hosts and self-folding guests Tetrahedron 2013, 69, 4541-4545
49. Han, T.; Chen, C.-F. Efficient potassium-ion-templated synthesis and controlled destruction of [2]rotaxanes based on cascade complexes J. Org. Chem. 2008, 73, 7735-7742
50. Guo, J.-B.; Jiang, Y.; Chen, C.-F. Self-assembled interwoven cages from triptycene-derived bis-macrotricyclic polyether and multiple branched paraquat-derived subunits Org. Lett. 2010, 12, 5764-5767
51. Jiang, Y.; Guo, J.-B.; Chen, C.-F. A new [3]rotaxane molecular machine based on a dibenzylammonium ion and a triazolium station Org. Lett. 2010, 12, 4248-4251
52. Meng, Z.; Xiang, J.-F.; Chen, C.-F. Tristable [ n ]rotaxanes: From molecular shuttle to molecular cable car Chem. Sci. 2014, 5, 1520-1525
53. Jiang, Y.; Guo, J.-B.; Chen, C.-F. A bifunctionalized [3]rotaxane and its incorporation into a mechanically interlocked polymer Chem. Commun. 2010, 46, 5536-5538
54. Zeng, F.; Shen, Y.; Chen, C.-F. Cross-linked supramolecular polymer networks with responsive and elastic gel properties via host-guest complexation: Controlled release of squaraine dyes Soft Matter 2013, 9, 4875-4882
55. Zeng, F.; Han, Y.; Yan, Z.-C.; Liu, C.-Y.; Chen, C.-F. Supramolecular polymer gel with multi stimuli responsive, self-healing and erasable properties generated by host-guest interactions Polymer 2013, 54, 6929-6935
56. Su, Y.-S.; Liu, J.-W.; Jiang, Y.; Chen, C.-F. Assembly of a self-complementary monomer: Formation of supramolecular polymer networks and responsive gels Chem.-Eur. J. 2011, 17, 2435-2441
57. Chen, C.-F.; Ma, Y.-X. Iptycene chemistry: From synthesis to applications; Springer-Verlag: Berlin Heidelberg, 2013.