Calix[n]imidazolium as a new class of positively charged homo-calix compounds

Nature Communications

Volumn 4, Issue , 2013, Pages

  Chun, Young ^a   Jiten Singh, N ^a,b   Hwang, In Chul ^a,c   Woo Lee, Jung ^a   Yu, Seong Uk ^a   Kim, Kwang S ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

^b Samsung SDI   (South Korea)

^c Sogang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; FLUORIDE; FULLERENE DERIVATIVE; IMIDAZOLE DERIVATIVE; IONIC LIQUID;

ALKENE; AQUEOUS SOLUTION; ARRAY; CRYSTALLINITY; FULLERENE; GRAPHITE; MOLECULAR ANALYSIS; STABILIZATION;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; SYNTHESIS; X RAY ANALYSIS;

EID: 84877767906     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms2758     Document Type: Article

References (50)

1. Lehn, J.-M. Supramolecular chemistry-scope and perspectives molecules, supermolecules, and molecular devices (Nobel Lecture). Angew. Chem. Int. Ed. 27, 89-112 (1988).
2. Shimizu, K. D. & Rebek, J. Synthesis and assembly of self-complementary calix[4]arenes. Proc. Natl Acad. Sci. USA 92, 12403-12407 (1995). (Pubitemid 26014078)
3. Schmidtchen, F. P. & Berger, M. Artificial organic host molecules for anions. Chem. Rev. 97, 1609-1646 (1997). (Pubitemid 127659607)
4. Vicens, J., Harrowfield, J. & Baklouti, L. Calixarenes in the Nanoworld (Springer, 2007).
5. Prins, L. J., Huskens, J., de Jong, F., Timmerman, P. & Reinhoudt, D. N. Complete asymmetric induction of supramolecular chirality in a hydrogen-bonded assembly. Nature 398, 498-502 (1999).
6. Hong, B. H. et al. Self-assembled arrays of organic nanotubes with infinitely long one-dimensional H-bond chains. J. Am. Chem. Soc 123, 10748-10749 (2001). (Pubitemid 33015724)
7. Hong, B. H., Bae, S. C., Lee, C. W., Jeong, S. & Kim, K. S. Ultrathin single-crystalline silver nanowire arrays formed in an ambient solution phase. Science 294, 348-351 (2001). (Pubitemid 32963397)
8. Sidorov, V. et al. Ion channel formation from a calix[4]arene amide that binds HCl. J. Am. Chem. Soc. 124, 2267-2278 (2002). (Pubitemid 34267113)
9. Casnati, A., Sansone, F. & Ungaro, R. Peptido-and glycocalixarenes: playing with hydrogen bonds around hydrophobic cavities. Acc. Chem. Res. 36, 246-254 (2003).
10. Shivanyuk, A. Nanoencapsulation of calix[4]arene inclusion complexes. J. Am. Chem. Soc. 129, 14196-14199 (2007). (Pubitemid 350171442)
11. Lee, J. Y. et al. Near-field focusing and magnification through self-assembled nanoscale spherical lenses. Nature 460, 498-501 (2009).
12. Kral, V. et al. Calix[4]pyridine: a new arrival in the heterocalixarene family. Chem. Commun. 9-10 (1998).
13. Gale, P. A., Sessler, J. L., Kral, V. & Lynch, V. Calix[4]pyrroles: old yet new anion-binding agents. J. Am. Chem. Soc. 118, 5140-5141 (1996). (Pubitemid 26202233)
14. Gale, P. A., Sessler, J. L. & Kral, V. Calixpyrroles. Chem. Commun. 1-8 (1998).
15. Miyaji, H., Sato, W. & Sessler, J. L. Naked-eye detection of anions in dichloromethane: colorimetric anion sensors based on calix[4]pyrrole. Angew. Chem. Int. Ed. 39, 1777-1780 (2000). (Pubitemid 30365755)
16. Gale, P. A., Anzenbacher, P. & Sessler, J. L. Calixpyrroles II. Coord. Chem. Rev. 222, 57-102 (2001).
17. Sessler, J. L. et al. Crown-6-calix[4]arene-capped calix[4]pyrrole: an ion-pair receptor for solvent-separated CsF ions. J. Am. Chem. Soc 130, 13162-13166 (2008).
18. Asfari, M.-Z. B. V., Harrowfield, J. & Vicens, J. Calixarenes 2001 (Springer, Netherlands, 2001).
19. Beer, P. D. & Schmitt, P. Molecular recognition of anions by synthetic receptors. Curr. Opin. Chem. Biol. 1, 475-482 (1997). (Pubitemid 127437848)
20. Wintergerst, M. P., Levitskaia, T. G., Moyer, B. A., Sessler, J. L. & Delmau, L. H. Calix[4]pyrrole: a new ion-pair receptor as demonstrated by liquid-liquid extraction. J. Am. Chem. Soc. 130, 4129-4139 (2008). (Pubitemid 351429884)
21. Sessler, J. L. et al. A calix[4]arene strapped calix[4]pyrrole: an ion-pair receptor displaying three different cesium cation recognition modes. J. Am. Chem. Soc. 132, 5827-5836 (2010).
22. Kishan, M. R., Rani, V. R., Kulkarni, S. J. & Raghavan, K. V. A new environmentally friendly method for the synthesis of calix(4)pyrroles over molecular sieve catalysts. J. Mol. Catal. A-Chemical 237, 155-160 (2005). (Pubitemid 40929483)
23. Wichmann, K. et al. Polyamine-based anion receptors: extraction and structural studies. Coord. Chem. Rev. 250, 2987-3003 (2006).
24. Seganish, J. L. et al. Regulating supramolecular function in membranes: calixarenes that enable or inhibit transmembrane Cl-transport. Angew. Chem. Int. Ed. 45, 3334-3338 (2006). (Pubitemid 44099004)
25. Eller, L. R. et al. Octamethyl-octaundecylcyclo[8]pyrrole:a promising sulfate anion extractant. J. Am. Chem. Soc. 129, 11020-11021 (2007). (Pubitemid 47435697)
26. Fowler, C. J. et al. Enhanced anion exchange for selective sulfate extraction: overcoming the Hofmeister bias. J. Am. Chem. Soc. 130, 14386-14387 (2008).
27. Yoon, J., Kim, S. K., Singh, N. J. & Kim, K. S. Imidazolium receptors for the recognition of anions. Chem. Soc. Rev. 35, 355-360 (2006). (Pubitemid 43475201)
28. Ihm, H. et al. Tripodal nitro-imidazolium receptor for anion binding driven by (C-H)(+)-X-hydrogen bonds. Org. Lett. 4, 2897-2900 (2002).
29. Sato, K., Arai, S. & Yamagishi, T. A new tripodal anion receptor with C-H center dot center dot center dot X-hydrogen bonding. Tetrahedron. Lett 40, 5219-5222 (1999). (Pubitemid 29307896)
30. Kwon, J. Y. et al. Fluorescent GTP-sensing in aqueous solution of physiological pH. J. Am. Chem. Soc. 126, 8892-8893 (2004). (Pubitemid 38971052)
31. Chellappan, K., Singh, N. J., Hwang, I. C., Lee, J. W. & Kim, K. S. A calix[4]imidazolium[2]pyridine as an anion receptor. Angew. Chem. Int. Ed. 44, 2899-2903 (2005). (Pubitemid 40689668)
32. Vickers, M. S., Martindale, K. S. & Beer, P. D. Imidazolium functionalised acyclic ruthenium(II) bipyridyl receptors for anion recognition and luminescent sensing. J. Mater. Chem. 15, 2784-2790 (2005). (Pubitemid 41048675)
33. Amendola, V. et al. A metal-based trisimidazolium cage that provides six C-H hydrogen-bond-donor fragments and includes anions. Angew. Chem. Int. Ed. 45, 6920-6924 (2006). (Pubitemid 44654495)
34. Garrison, J. C., Simons, R. S., Kofron, W. G., Tessier, C. A. & Youngs, W. J. Synthesis and structural characterization of a silver complex of a mixeddonor N-heterocyclic carbene linked cyclophane. Chem. Commun. 1780-1781 (2001). (Pubitemid 32906777)
35. Alcalde, E., Ramos, S. & Pérez-García, L. Anion template-directed synthesis of dicationic [14]imidazoliophanes. Org. Lett. 1, 1035-1038 (1999).
36. Ramos, S., Alcalde, E., Doddi, G., Mencarelli, P. & Perez-Garcia, L. Quantitative evaluation of the chloride template effect in the formation of dicationic [1(4)]imidazoliophanes. J. Org. Chem. 67, 8463-8468 (2002). (Pubitemid 35407423)
37. Gong, H. Y., Rambo, B. M., Karnas, E., Lynch, V. M. & Sessler, J. L. A'Texas-sized' molecular box that forms an anion-induced supramolecular necklace. Nat. Chem 2, 406-409 (2010).
38. Serpell, C. J., Cookson, J., Thompson, A. L. & Beer, P. D. A dual-functional tetrakis-imidazolium macrocycle for supramolecular assembly. Chem. Sci. 2, 494-500 (2011).
39. Wong, W. W. H., Vickers, M. S., Cowley, A. R., Paul, R. L. & Beer, P. D. Tetrakis(imidazolium) macrocyclic receptors for anion binding. Org. Biomol. Chem. 3, 4201-4208 (2005). (Pubitemid 41801591)
40. Cametti, M. & Rissanen, K. Recognition and sensing of fluoride anion. Chem. Commun. 2809-2829 (2009).
41. Brodesser, G. & Vögtle, F. Homocalixarenes and homocalixpyridines. J. Inclusion Phenom. Macrocyclic Chem 19, 111-135 (1994).
42. Kim, K. S., Singh, N. J., Min, S. K. & Kim, D. Y. Comprehensive energy analysis for various types of pi-interaction. J. Chem. Theor. Comput. 5, 515-529 (2009).
43. Viciano, M. et al. An N-heterocyclic carbene/iridium hydride complex from the oxidative addition of a ferrocenyl-bisimidazolium salt: implications for synthesis. Angew. Chem. Int. Ed. 44, 444-447 (2005). (Pubitemid 40138353)
44. Arnold, P. L. & Pearson, S. Abnormal N-heterocyclic carbenes. Coord. Chem. Rev. 251, 596-609 (2007).
45. Youngs, W. J., Hindi, K. M., Panzner, M. J., Tessier, C. A. & Cannon, C. L. The medicinal applications of imidazolium carbene-metal complexes. Chem. Rev. 109, 3859-3884 (2009).
46. Cazin, C. S. J., Citadelle, C. A., Le Nouy, E., Bisaro, F. & Slawin, A. M. Z. Simple and versatile synthesis of copper and silver N-heterocyclic carbene complexes in water or organic solvents. Dalton Trans. 39, 4489-4491 (2010).
47. Hahn, F. E. & Jahnke, M. C. Heterocyclic carbenes: synthesis and coordination chemistry. Angew. Chem. Int. Ed. 47, 3122-3172 (2008).
48. Pádua, A. A. H., Costa Gomes, M. F. & Canongia Lopes, J. N. A. Molecular solutes in ionic liquids: a structural perspective. Acc. Chem. Res. 40, 1087-1096 (2007).
49. Baldelli, S. Surface structure at the ionic liquid-electrified metal interface. Acc. Chem. Res. 41, 421-431 (2008).
50. Schneider, H. J., Schiestel, T. & Zimmermann, P. Host-guest supramolecular chemistry. 34. The incremental approach to noncovalent interactions: coulomb and van der Waals effects in organic ion pairs. J. Am. Chem. Soc. 114, 7698-7703 (1992).