Self-assembling organic nanotubes with precisely defined, sub-nanometer pores: Formation and mass transport characteristics

Accounts of Chemical Research

Volumn 46, Issue 12, 2013, Pages 2856-2866

  Gong, Bing ^a,b   Shao, Zhifeng ^c  

^a UNIVERSITY AT BUFFALO   (United States)

^b BEIJING NORMAL UNIVERSITY   (China)

^c SHANGHAI JIAO TONG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

HYDRAZINE; HYDRAZINE DERIVATIVE; MACROCYCLIC COMPOUND; NANOTUBE; ORGANIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ION TRANSPORT; POROSITY;

HYDRAZINES; ION TRANSPORT; MACROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; NANOTUBES; ORGANIC CHEMICALS; POROSITY;

EID: 84890660206     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar400030e     Document Type: Article

References (67)

1. Bocquet, L.; Charlaix, E. Nanofluidics, from bulk to interfaces Chem. Soc. Rev. 2010, 39, 1073-1095
2. Aidley, D. J. The Physiology of Excitable Cells, 4 th ed.; Cambridge University Press: Cambridge, U.K., 1998.
3. Hille, B. Ion Channels of Excitable Membranes, 3 rd ed.; Sinauer: Sunderland, MA, 2001.
4. Agre, P. Aquaporin water channels (nobel lecture) Angew. Chem., Int. Ed. 2004, 43, 4278-4290 (Pubitemid 39257402)
5. Hummer, G.; Rasaiah, J. C.; Noworyta, J. P. Water conduction through the hydrophobic channel of a carbon nanotube Nature 2001, 414, 188-190 (Pubitemid 33051229)
6. Holt, J. K.; Park, H. G.; Wang, Y. M.; Stadermann, M.; Artyukhin, A. B.; Grigoropoulos, C. P.; Noy, A.; Bakajin, O. Fast mass transport through sub-2-nanometer carbon nanotubes Science 2006, 312, 1034-1037
7. Carrillo-Tripp, M.; Saint-Martin, H.; Ortega-Blake, I. Minimalist molecular model for nanopore selectivity Phys. Rev. Lett. 2004, 93 168104
8. + inside carbon nanotubes Nano Lett. 2009, 9, 989-994
9. Jirage, K. B.; Hulteen, J. C.; Martin, C. R. Nanotubule-based molecular-filtration membranes Science 1997, 278, 655-658 (Pubitemid 27464957)
10. Yang, S. Y.; Ryu, I.; Kim, H. Y.; Kim, J. K.; Jang, S. K.; Russell, T. P. Nanoporous membranes with ultrahigh selectivity and flux for the filtration of viruses Adv. Mater. 2006, 18, 709-712
11. Gankema, H.; Hempenius, M. A.; Möller, M.; Johansson, G. Gel template leaching: An approach to functional nanoporous membranes Macromol. Symp. 1996, 102, 381-390
12. Beginn, U.; Zipp, G.; Mourran, A.; Walther, P.; Möller, M. Membranes containing oriented supramolecular transport channels Adv. Mater. 2000, 12, 513-516 (Pubitemid 30588989)
13. Czaplewski, K. F.; Hupp, J. T.; Snurr, R. Q. Molecular squares as molecular sieves: Size-selective transport through porous-membrane-supported thin-film materials Adv. Mater. 2001, 13, 1895-1897 (Pubitemid 34061207)
14. Yan, X.; Janout, V.; Hsu, J. T.; Regen, S. L. A polymerized calix[6]arene monolayer having gas permeation selectivity that exceeds Knudsen diffusion J. Am. Chem. Soc. 2002, 124, 10962-10963 (Pubitemid 35025640)
15. Akthuakul, A.; Salinara, R. F.; Mayes, A. M. Antifouling polymer membranes with subnanometer size selectivity Macromolecules 2004, 37, 7663-7668
16. Bong, D. T.; Clark, T. D.; Granja, J. R.; Ghadiri, M. R. Self-assembling organic nanotubes Angew. Chem., Int. Ed. 2001, 40, 988-1011
17. Baumeister, B.; Sakai, N.; Matile, S. Giant artificial ion channels formed by self-assembled, cationic rigid-rod beta-barrels Angew. Chem., Int. Ed. 2000, 39, 1955-1958 (Pubitemid 30399133)
18. Block, M. A. B.; Kaiser, C.; Khan, A.; Hecht, S. Discrete organic nanotubes based on a combination of covalent and non-covalent approaches Top. Curr. Chem. 2005, 245, 89-150 (Pubitemid 44423490)
19. Moralez, J. G.; Raez, J.; Yamazaki, T.; Motkuri, R. K.; Kovalenko, A.; Fenniri, H. Helical rosette nanotubes with tunable stability and hierarchy J. Am. Chem. Soc. 2005, 127, 8307-8309 (Pubitemid 40828148)
20. Jonkheijm, P.; Miura, A.; Zdanowska, M.; Hoeben, F. J. M.; De Feyter, S.; Schenning, A. P. H. J.; De Schryver, F. C.; Meijer, E. W. pi-conjugated oligo-(p -phenylenevinylene) rosettes and their tubular self-assembly Angew. Chem., Int. Ed. 2004, 43, 74-78 (Pubitemid 38063475)
21. Zhou, M. J.; Nemade, P. R.; Lu, X. Y.; Zeng, X. H.; Hatakeyama, E. S.; Noble, R. D.; Gin, D. L. New type of membrane material for water desalination based on a cross-linked bicontinuous cubic lyotropic liquid crystal assembly J. Am. Chem. Soc. 2007, 129, 9574-9575 (Pubitemid 47237453)
22. Percec, V.; Dulcey, A. E.; Balagurusamy, V. S. K.; Miura, Y.; Smidrkal, J.; Peterca, M.; Nummelin, S.; Edlund, U.; Hudson, S. D.; Heiney, P. A.; Hu, D. A.; Magonov, S. N.; Vinogradov, S. A. Self-assembly of amphiphilic dendritic dipeptides into helical pores Nature 2004, 430, 764-768 (Pubitemid 39071343)
23. Schnur, J. M. Lipid tubules-A paradigm for molecularly engineered structures Science 1993, 262, 1669-1676 (Pubitemid 24031377)
24. Ghadiri, M. R.; Granja, J. R.; Milligan, R. A.; McRee, D. E.; Khazanovich, N. Self-assembling organic nanotubes based on a cyclic peptide architecture Nature 1993, 366, 324-327 (Pubitemid 23349358)
25. Seebach, D.; Matthews, J. L.; Meden, A.; Wessels, T.; Baerlocher, C.; McCusker, L. B. Cyclo-beta-peptides: Structure and tubular stacking of cyclic tetramers of 3-aminobutanoic acid as determined from powder diffraction data Helv. Chim. Acta 1997, 80, 173-182
26. Gattuso, G.; Menzer, S.; Nepogodiev, S. A.; Stoddart, J. F.; Williams, D. J. Carbohydrate nanotubes Angew. Chem., Int. Ed. 1997, 36, 1451-1454
27. Moore, J. S. Shape-persistent molecular architectures of nanoscale dimension Acc. Chem. Res. 1997, 30, 402-413 (Pubitemid 127472591)
28. Haley, M. M.; Pak, J. J.; Brand, S. C. Macrocyclic oligo(phenylacetylenes) and oligo(phenyldiacetylenes) Top. Curr. Chem. 1999, 201, 81-130
29. Yuan, L. H.; Feng, W.; Yamato, K.; Sanford, A. R.; Xu, D. G.; Guo, H.; Gong, B. Highly efficient, one-step macrocyclizations assisted by backbone-preorganization J. Am. Chem. Soc. 2004, 126, 11120-11121 (Pubitemid 39223163)
30. Zhao, D. H.; Moore, J. S. Shape-persistent arylene ethynylene macrocycles: Syntheses and supramolecular chemistry Chem. Commun. 2003, 807-818 (Pubitemid 36461167)
31. Höger, S. Shape-persistent macrocycles: From molecules to materials Chem.-Eur. J. 2004, 10, 1320-1329
32. Grave, C.; Schlüter, A. D. Shape-persistent, nano-sized macrocycles Eur. J. Org. Chem. 2002, 3075-3098
33. Bunz, U. H. F.; Rubin, Y.; Tobe, Y. Polyethynylated cyclic pi-systems: Scaffoldings for novel two and three-dimensional carbon networks Chem. Soc. Rev. 1999, 28, 107-119
34. Gallant, A. J.; MacLachlan, M. J. Ion-induced tubular assembly of conjugated Schiff-base macrocycles Angew. Chem., Int. Ed. 2003, 42, 5307
35. Seo, S. H.; Chang, J. Y.; Tew, G. N. Self-assembled vesicles from an amphiphilic ortho-phenylene ethynylene macrocycle Angew. Chem., Int. Ed. 2006, 45, 7526-7530 (Pubitemid 44851672)
36. Zhang, C.-X.; Wang, Q.; Long, H.; Zhang, W. A highly c70-selective shape-persistent rectangular prism constructed through one-step alkyne metathesis J. Am. Chem. Soc. 2011, 133, 20995-21001
37. Gong, B. Hollow crescents, helices and macrocycles from enforced folding and folding-assisted macrocyclization Acc. Chem. Res. 2008, 41, 1376-1386
38. Yamato, K.; Kline, M.; Gong, B. Cavity-containing, backbone-rigidified foldamers and macrocycles Chem. Commun. 2012, 48, 12142-12158
39. Gong, B.; Zeng, H. Q.; Zhu, J.; Yuan, L. H.; Han, Y. H.; Cheng, S. Z.; Furukawa, M.; Parra, R. D.; Kovalevsky, A. Y.; Mills, J. L.; Skrzypczak-Jankun, E.; Martinovic, S.; Smith, R. D.; Zheng, C.; Szyperski, T.; Zeng, X. C. Creating nanocavities of tunable sizes: Hollow helices Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 11583-11588 (Pubitemid 34994442)
40. Feng, W.; Yamato, K.; Yang, L. Q.; Ferguson, J.; Zhong, L. J.; Zou, S. L.; Yuan, L. H.; Zeng, X. C.; Gong, B. Efficient kinetic macrocyclization J. Am. Chem. Soc. 2009, 131, 2629-2637
41. Ferguson, J. S.; Yamato, K.; Liu, R.; He, L.; Zeng, X. C.; Gong, B. One-pot formation of large macrocycles with modifiable peripheries and internal cavities Angew. Chem., Int. Ed. 2009, 48, 3150-3154
42. Yang, Y. A.; Feng, W.; Hu, J. C.; Zou, S. L.; Gao, R. Z.; Yamato, K.; Kline, M.; Cai, Z. H.; Gao, Y.; Wang, Y. B.; Li, Y. B.; Yang, Y. L.; Yuan, L. H.; Zeng, X. C.; Gong, B. Strong aggregation and directional assembly of aromatic oligoamide macrocycles J. Am. Chem. Soc. 2011, 133, 18590-18593
43. Zhou, X. B.; Liu, G. D.; Yamato, K.; Shen, Y.; Cheng, R. X.; Wei, X. X.; Bai, W. L.; Gao, Y.; Li, H.; Liu, Y.; Liu, F. T.; Czajkowsky, D. M.; Wang, J. F.; Dabney, M. J.; Cai, Z. H.; Hu, J.; Bright, F. V.; He, L.; Zeng, X. C.; Shao, Z. F.; Gong, B. Self-assembling sub-nanometer pores with unusual mass-transporting properties Nature Commun. 2012, 3 949
44. Lear, J. D.; Wasserman, Z. R.; DeGrado, W. F. Synthetic amphiphilic peptide models for protein ion channels Science 1988, 240, 1177-1181
45. Kubik, S. Large increase in cation binding affinity of artificial cyclopeptide receptors by an allosteric effect J. Am. Chem. Soc. 1999, 121, 5846-5855 (Pubitemid 29305122)
46. + selectivity Angew. Chem., Int. Ed. 1995, 34, 693-694
47. Cazacu, A.; Tong, C.; van der Lee, A.; Fyles, T. M.; Barboiu, M. Columnar self-assembled ureido crown ethers: An example of ion-channel organization in lipid bilayers J. Am. Chem. Soc. 2006, 128, 9541-9548 (Pubitemid 44117111)
48. Ma, L.; Melegari, M.; Colombini, M.; Davis, J. T. Large and stable transmembrane pores from guanosine-bile acid conjugates J. Am. Chem. Soc. 2008, 130, 2938-2939 (Pubitemid 351455956)
49. Liu, P.; Ni, R.; Mehta, A. K.; Childers, W. S.; Lakdawala, A.; Pingali, S. V.; Thiyagarajan, P.; Lynn, D. G. Nucleobase-directed amyloid nanotube self-assembly J. Am. Chem. Soc. 2008, 130, 16867-16869
50. Negin, S.; Daschbach, M. M.; Kulikov, O. V.; Rath, N.; Gokel, G. W. Pore formation in phospholipid bilayers by branched-chain pyrogallol[4]arenes J. Am. Chem. Soc. 2011, 133, 3234-3237
51. Kaucher, M. S.; Peterca, M.; Dulcey, A. E.; Kim, A. J.; Vinogradov, S. A.; Hammer, D. A.; Heiney, P. A.; Percec, V. Selective transport of water mediated by porous dendritic dipeptides J. Am. Chem. Soc. 2007, 129, 11698-11699 (Pubitemid 47479916)
52. + channels J. Am. Chem. Soc. 2007, 129, 11698-11699
53. Si, W.; Chen, L.; Hu, X. B.; Tang, G. F.; Chen, Z. X.; Hou, J. L.; Li, Z. T. Selective artificial transmembrane channels for protons by formation of water wires Angew. Chem., Int. Ed. 2011, 50, 12564-12568
54. Matile, S.; Jentzsch, A. V.; Montenegro, J.; Fin, A. Recent synthetic transport systems Chem. Soc. Rev. 2011, 40, 2453-2474
55. Chui, J. K.; Fyles, T. M. Ionic conductance of synthetic channels: Analysis, lessons, and recommendations Chem. Soc. Rev. 2012, 41, 148-175
56. Negin, S.; Smith, B. A.; Unger, A.; Leevy, W. M.; Gokel, G. W. Hydraphiles: A rigorously studied class of synthetic channel compounds with in vivo activity Int. J. Biomed. Imaging 2013, 2013 803579
57. Wu, Z. H.; Hu, T.; He, L.; Gong, B. One-pot formation of aromatic tetraurea macrocycles Org. Lett. 2012, 14, 2504-2507
58. He, L.; An, Y.; Yuan, L. H.; Feng, W.; Li, M. F.; Zhang, D. C.; Yamato, K.; Zheng, C.; Zeng, X. C.; Gong, B. Cavity-containing macrocyclic aromatic tetrasulfonamides based on a well-defined structural motif Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 10850-10855
59. Geng, M. W.; Zhang, D. C.; Wu, X. X.; He, L.; Gong, B. One-pot formation and characterization of macrocyclic aromatic tetrasulfonates Org. Lett. 2009, 11, 923-926
60. Smithrud, D. B.; Diederich, F. Strength of molecular complexation of apolar solutes in water and in organic solvents is predictable by linear free energy relationships: A general model for solvation effects on apolar binding J. Am. Chem. Soc. 1990, 112, 339-343 (Pubitemid 20090627)
61. Helsel, A. J.; Brown, A. L.; Yamato, K.; Feng, W.; Yuan, L. H.; Clements, A.; Harding, S. V.; Szabo, G.; Shao, Z. F.; Gong, B. Highly conducting transmembrane pores formed by aromatic oligoamide macrocycles J. Am. Chem. Soc. 2008, 130, 15784-15785
62. (L,D) helix Proc. Natl. Acad. Sci. U. S. A. 1971, 62, 672-676
63. Kasianowicz, J. J.; Eric Brandin, E.; Branton, D.; Deamer, D. W. Characterization of individual polynucleotide molecules using a membrane channel Proc. Natl. Acad. Sci. U. S. A. 2006, 93, 13770-13773
64. Vijayvergiya, V.; Wilson, R.; Chorak, A.; Gao, P. F.; Cross, T. A.; Busat, H. D. D. Proton conductance of influenza virus M2 protein in planar lipid bilayers Biophys. J. 2004, 87, 1697-1704 (Pubitemid 39167026)
65. Sakai, N.; Matile, S. The determination of the ion selectivity of synthetic ion channels and pores in vesicles J. Phys. Org. Chem. 2006, 19, 452-460 (Pubitemid 46165853)
66. Zeidel, M. L.; Ambudkar, S. V.; Smith, B. L.; Agre, P. Reconstitution of functional water channels in liposomes containing purified red cell chip28 protein Biochemistry 1992, 31, 7436-7440
67. Deamer, D. W.; Nichols, J. W. Proton-hydroxide permeability of liposomes Proc. Natl. Acad. Sci. U. S. A. 1983, 80, 165-168