Porphyrin-cucurbituril organic molecular porous material: Structure and iodine adsorption properties

Inorganic Chemistry Communications

Volumn 35, Issue , 2013, Pages 156-159

  Xiao, Xin ^a,b   Li, Wenjun ^a   Jiang, Jianzhuang ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY BEIJING   (China)

^b GUIZHOU UNIVERSITY   (China)

Author keywords

Host guest complex; Organic molecular porous material; Porphyrin; TMeQ 6

Indexed keywords

EID: 84880181804     PISSN: 13877003     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.inoche.2013.06.012     Document Type: Article

References (47)

1. G. Parvari, O. Reany, and E. Keinan Applicable properties of cucurbiturils Isr. J. Chem. 51 2011 646 663 (and references therein)
2. F. Wang, H.-W. Gu, and T.M. Swager Carbon nanotube/polythiophene chemiresistive sensors for chemical warfare agents J. Am. Chem. Soc. 130 2008 5392 5393 (Pubitemid 351612925)
3. W.M. Nau, G. Ghale, A. Hennig, H. Bakirci, and D.M. Bailey Substrate-selective supramolecular tandem assays: monitoring enzyme inhibition of arginase and diamine oxidase by fluorescent dye displacement from calixarene and cucurbituril macrocycles J. Am. Chem. Soc. 131 2009 11558 11570
4. Z.-S. Wu, Y. Sun, Y.-Z. Tan, S.-B. Yang, X.-L. Feng, and K. Müllen Three-dimensional graphene-based macro and mesoporous frameworks for high-performance electrochemical capacitive energy storage J. Am. Chem. Soc. 134 2012 19532 19535
5. J. Meeuwissen, and J.N.H. Reek Supramolecular catalysis beyond enzyme mimics Nat. Chem. 2 2010 615 621
6. J. Porel. Mintu, M.F. Steffen, N.J. Ottaviani, V. Turro, and Ramamurthy Interaction between encapsulated excited organic molecules and free nitroxides: communication across a molecular wall Langmuir 27 2011 10548 10555
7. X. Xiao, Z.-C. Tian, L. He, S.-F. Xue, Y.-Q. Zhang, Q.-J. Zhu, and Z. Tao Supra-molecular assemblies of host-guest complexes of cucurbit[6]uril with some organic molecules J. Mol. Struct. 965 2010 109 115
8. Q.-L. Wu, Y.-Y. Cheng, J.-J. Hu, L.-B. Zhao, and T.-W. Xu Insights into the Interactions between dendrimers and bioactive surfactants: 3. Size-dependent and hydrophobic property-dependent encapsulation of bile salts J. Phys. Chem. B 113 2009 12934 12943
9. K. Chen, Y.-F. Hu, X. Xiao, S.-F. Xue, Z. Tao, Y.-Q. Zhang, Q.-J. Zhu, and J.-X. Liu Homochiral 1D-helical coordination polymers from achiral cucurbit[5]uril: hydroquinone-induced spontaneous resolution RSC Adv. 2 2012 3217 3220
10. P. Pierre L-Cysteine as a chiral linker in lanthanide-cucurbit[6]uril one-dimensional assemblies Inorg. Chem. 50 2011 10558 10560
11. C. Ortiz Mellet, J.M. García Fernández, and J.M. Benito Targeted nanoparticles, optical imaging and cancer Chem. Soc. Rev. 40 2011 1586 1608 (and references therein)
12. J.M. Chinai, A.B. Taylo, L.M. Ryno, N.D. Hargreaves, C.A. Morris, P.J. Hart, and A.R. Urbach Molecular recognition of insulin by a synthetic receptor J. Am. Chem. Soc. 133 2011 8810 8813
13. K. Kim, N. Selvapalam, Y.-H. Ko, K.-M. Park, D. Kim, and J. Kim Functionalized cucurbiturils and their applications Chem. Soc. Rev. 36 2007 267 279
14. J. Lagona, P. Mukhopadhyay, S. Chakrabarti, and L. Isaacs The cucurbit[n]uril family Angew. Chem. Int. Ed. 44 2005 4844 4870 (Pubitemid 41138666)
15. W.-H. Lei, Q.-X. Zhou, G.-Y. Jiang, Y.-J. Hou, B.-W. Zhang, X.-X. Cheng, and X.-S. Wang Host-guest interaction of Hoechst 34580 and cucurbit[7]uril ChemPhysChem 12 2011 2933 2940
16. S.-G. Sun, W.-Y. Gao, F.-Y. Liu, J.-L. Fan, and X.-J. Peng Study of an unusual charge-transfer inclusion complex with NIR absorption, and its application for DNA photocleavage J. Mater. Chem. 20 2010 5888 5892
17. M.-N. Cao, Y. Wei, S.-Y. Gao, and R. Cao Synthesis of palladium nanocatalysts with cucurbit[n]uril as both a protecting agent and a support for Suzuki and Heck reactions Catal. Sci. Technol. 2 2012 156 163
18. E. Masson, X.-X. Ling, R. Joseph, K.-M. Lawrence, and X.-Y. Lu Cucurbituril chemistry: a tale of supramolecular success RSC Adv. 2 2012 1213 1247
19. H. Cong, Z. Tao, S.-F. Xue, and Q.-J. Zhu Host-induced chemical control: supramolecular catalysis based on the host-guest interaction of cucurbit[n]urils Curr. Org. Chem. 15 2011 86 95
20. I. Ghosh, and W.M. Nau The strategic use of supramolecular pKa shifts to enhance the bioavailability of drugs Adv. Drug Deliv. Rev. 64 2012 764 783
21. N. Barooah, J. Mohanty, H. Pal, and A.C. Bhasikuttan Stimulus-responsive supramolecular pKa tuning of cucurbit[7]uril encapsulated coumarin 6 dye J. Phys. Chem. B 116 2012 3683 3689
22. N. Dong, L.-N. Cheng, X.-L. Wang, Q. Li, C.-Y. Dai, and Z. Tao Significant fluorescence enhancement by supramolecular complex formation between berberine chloride and cucurbit(n = 7)uril and its analytical application Talanta 84 2011 684 689
23. Y.H. Ko, K. Kim, J.K. Kang, H. Chun, J.W. Lee, S. Sakamoto, K. Yamaguchi, J.C. Fettinger, and K. Kim Designed self-assembly of molecular necklaces using host-stabilized charge-transfer interactions J. Am. Chem. Soc. 126 2004 1932 1933 (Pubitemid 38228863)
24. K.M. Park, S.Y. Kim, J. Heo, D. Whang, S. Sakamoto, K. Yamaguchi, and K. Kim Q6-designed self-assembly of molecular necklaces J. Am. Chem. Soc. 124 2002 2140 2147
25. E. Lee, J. Heo, and K. Kim A three-dimensional polyrotaxane network Angew. Chem. Int. Ed. 39 2000 2699 2701 (Pubitemid 30629190)
26. S. Angelos, Y.-W. Yang, K. Patel, J.F. Stoddart, and J.I. Zink pH-Responsive supramolecular nanovalves based on cucurbit[6]uril pseudorotaxanes Angew. Chem. Int. Ed. 47 2008 2222 2226
27. Y.-J. Zhao, M.H. Pourgholami, D.L. Morris, J.G. Collins, and A.I. Day Enhanced cytotoxicity of benzimidazole carbamate derivatives and solubilisation by encapsulation in cucurbit[n]uril Org. Biomol. Chem. 8 2010 3328 3337
28. U. Pischel, D.U. Vanya, R. Patricia, and W.M. Nau Supramolecular logic with macrocyclic input and competitive reset Chem. Commun. 46 2010 2635 2637
29. E.A. Appel, F. Biedermann, U. Rauwald, S.T. Jones, J.M. Zayed, and O.A. Scherman Supramolecular cross-linked networks via host-guest complexation with cucurbit[8]uril J. Am. Chem. Soc. 132 2010 14251 14260
30. X. Xiao, J.-X. Liu, K. Chen, Q.-J. Zhu, S.-F. Xue, and Z. Tao Metal cation controlled supramolecular assembly of 1-butyl-4,4′-bipyridinium and cucurbit[8]uril Eur. J. Inorg. Chem. 19 2010 2956 2961
31. Y.H. Ko, E. Kim, I. Hwang, and K. Kim Supramolecular assemblies built with host-stabilized charge-transfer interactions Chem. Commun. 13 2007 1305 1315 (Pubitemid 46465976)
32. Y.H. Ko, Y. Kim, H. Kim, and K. Kim U-shaped conformation of alkyl chains bound to a synthetic receptor cucurbit[8]uril Chem. Asian. J. 6 2011 652 657
33. H.Y. Ko, H. Kim, Y. Kim, and K. Kim U-shaped conformation of alkyl chains bound to a synthetic host Angew. Chem. Int. Ed. 47 2008 4106 4109
34. X. Xiao, Q. Wang, Y.-H. Yu, Z.-Y. Xiao, Z. Tao, S.-F. Xue, Q.-J. Zhu, J.-X. Liu, and X.-H. Liu Contorted conformation of 1,4-butylidene-dipyridinium and 1,10-decylidene-dipyridinium cationic guests in cucurbit[8]uril host Eur. J. Org. Chem. 12 2011 2366 2371
35. X. Xiao, J.-X. Liu, Z.-F. Fan, K. Chen, Q.-J. Zhu, S.-F. Xue, and Z. Tao Chirality from achiral components: N, N′-bis(4-dimethylaminobenzyl) dodecane-1,12-diammonium in cucurbit[8]uril Chem. Commun. 46 2010 3741 3743
36. J.-P. Zeng, H. Cong, K. Chen, Z. Tao, S.-F. Xue, Q.-J. Zhu, Y.-Q. Zhang, and J.-X. Liu A novel strategy to assemble achiral ligands to chiral helical polyrotaxane structures Inorg. Chem. 50 2011 6521 6525
37. Y.-J. Zhao, S.-F. Xue, Q.-J. Zhu, Z. Tao, J.-X. Zhang, Z.-B. Wei, L.-S. Long, M.-L. Hu, H.-P. Xiao, and A.I. Day Synthesis of a symmetrical tetrasubstituted cucurbit[6]uril and its host-guest inclusion complex with 2,2 ′-bipyridine Chin. Sci. Bull. 49 2004 1111 1116 (Pubitemid 44552889)
38. X. Ma, A. Urbas, and Q. Li Controllable self-assembling of gold nanorods via on and off supramolecular noncovalent interactions Langmuir 28 2012 16263 16267
39. K. Watanabe, H. Kitagishi, and K. Kano Supramolecular ferric porphyrins as cyanide receptors in aqueous solution ACS Med. Chem. Lett. 2 2011 943 947
40. D. Tuncel, N. Cindir, and U. Koldemir [5]Rotaxane and [5]pseudorotaxane based on cucurbit[6]uril and anchored to a meso-tetraphenyl porphyrin J. Incl. Phenom. Macro. Chem. 55 2006 373 380 (Pubitemid 44127279)
41. J. Mohanty, A.C. Bhasikuttan, S.D. Choudhury, and H. Pal Noncovalent interaction of 5,10,15,20-tetrakis(4-N-methylpyridyl)porphyrin with cucurbit[7]uril: a supramolecular architecture J. Phys. Chem. B 112 2008 10782 10785
42. S.-M. Liu, A.D. Shukla, S. Gadde, B.D. Wagner, E. Kaifer, and L. Isaacs Ternary complexes comprising cucurbit[10]uril, porphyrins, and guests Angew. Chem. Int. Ed. 47 2008 2657 2660
43. W.-H. Lei, G.-Y. Jiang, Q.-X. Zhou, B.-W. Zhang, and X.-S. Wang Greatly enhanced binding of a cationic porphyrin towards bovine serum albumin by cucurbit[8]uril Phys. Chem. Chem. Phys. 12 2010 13255 13260
44. J.-F. Qian, X.-Y. Wu, Y.-L. Cao, X.-P. Ai, and H.-X. Yang High capacity and rate capability of amorphous phosphorus for sodium ion batteries Angew. Chem. Int. Ed. 52 2013 4633 4636
45. M.-H. Zeng, Q.-X. Wang, Y.-X. Tan, S. Hu, H.-X. Zhao, L.-S. Long, and M. Kurmoo Rigid pillars and double walls in a porous metal-organic framework: single-crystal to single-crystal, controlled uptake and release of iodine and electrical conductivity J. Am. Chem. Soc. 132 2010 2561 2563
46. Z. Yin, Q.-X. Wang, and M.-H. Zeng Iodine release and recovery, influence of polyiodide anions on electrical conductivity and nonlinear optical activity in an interdigitated and interpenetrated bipillared-bilayer metal-organic framework J. Am. Chem. Soc. 134 2012 4857 4863
47. T. Hasell, M. Schmidtmann, and A.I. Cooper Molecular doping of porous organic cages J. Am. Chem. Soc. 133 2011 14920 14923