Reticular synthesis of porous molecular 1D nanotubes and 3D networks

Nature Chemistry

Volumn 9, Issue 1, 2017, Pages 17-25

  Slater, A G ^a   Little, M A ^b   Pulido, A ^a   Chong, S Y ^a   Holden, D ^a   Chen, L ^a   Morgan, C ^a   Wu, X ^a   Cheng, G ^a   Clowes, R ^a   Briggs, M E ^a   Hasell, T ^a   Jelfs, K E ^c   Day, G M ^b   Cooper, A I ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^c IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85015298791     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.2663     Document Type: Article

References (58)

1. Moulton, B. & Zaworotko, M. J. From molecules to crystal engineering: supramolecular isomerism and polymorphism in network solids. Chem. Rev. 101, 1629-1658 (2001).
2. Desiraju, G. R. Crystal engineering: from molecule to crystal. J. Am. Chem. Soc. 135, 9952-9967 (2013).
3. Mastalerz, M. Shape-persistent organic cage compounds by dynamic covalent bond formation. Angew. Chem. Int. Ed. 49, 5042-5053 (2010).
4. Chen, L. et al. Separation of rare gases and chiral molecules by selective binding in porous organic cages. Nat. Mater. 13, 954-960 (2014).
5. Slater, A. G. & Cooper, A. I. Function-led design of new porous materials. Science 348, 8075 (2015).
6. Desiraju, G. R. Hydrogen bridges in crystal engineering: interactions without borders. Acc. Chem. Res. 35, 565-573 (2002).
7. Blake, A. J. et al. Inorganic crystal engineering using self-assembly of tailored building-blocks. Coord. Chem. Rev. 183, 117-138 (1999).
8. Kitagawa, S., Kitaura, R. & Noro, S. Functional porous coordination polymers. Angew. Chem. Int. Ed. 43, 2334-2375 (2004).
9. Simard, M., Su, D. & Wuest, J. D. Use of hydrogen-bonds to control molecular aggregation-self-assembly of 3-dimensional networks with large chambers. J. Am. Chem. Soc. 113, 4696-4698 (1991).
10. Hoskins, B. F. & Robson, R. Design and construction of a new class of scaffolding-like materials comprising infinite polymeric frameworks of 3Dlinked molecular rods. A reappraisal of the Zn(CN)2 and Cd(CN)2 structures and the synthesis and structure of the diamond-related frameworks [N(CH3)4] [CuIZnII(CN)4] and CuI[4,4',4?,4-tetracyanotetraphenylmethane]BF4.x C6H5NO2. J. Am. Chem. Soc. 112, 1546-1554 (1990).
11. Kondo, M., Yoshitomi, T., Seki, K., Matsuzaka, H. & Kitagawa, S. Threedimensional framework with channeling cavities for small molecules: {[M2(4,4?-bpy)3(NO3)4] xH2O}n (M = Co, Ni, Zn). Angew. Chem. Int. Ed. 36, 1725-1727 (1997).
12. Eddaoudi, M. et al. Systematic design of pore size and functionality in isoreticular MOFs and their application in methane storage. Science 295, 469-472 (2002).
13. Ferey, G. et al. A chromium terephthalate-based solid with unusually large pore volumes and surface area. Science 309, 2040-2042 (2005).
14. Furukawa, H., Cordova, K. E., O?Keeffe, M. & Yaghi, O. M. The chemistry and applications of metal-organic frameworks. Science 341, 1230444 (2013).
15. Ducharme, Y. & Wuest, J. D. Use of hydrogen-bonds to control molecular aggregation-extensive, self-complementary arrays of donors and acceptors. J. Org. Chem. 53, 5787-5789 (1988).
16. Zerkowski, J. A., Seto, C. T. & Whitesides, G. M. Solid-state structures of rosette and crinkled tape motifs derived from the cyanuric acid melamine lattice. J. Am. Chem. Soc. 114, 5473-5475 (1992).
17. Mitra, T. et al. Molecular shape sorting using molecular organic cages. Nat. Chem. 5, 276-281 (2013).
18. Zhang, G., Presly, O., White, F., Oppel, I. M. & Mastalerz, M. A permanent mesoporous organic cage with an exceptionally high surface area. Angew. Chem. Int. Ed. 53, 1516-1520 (2014).
19. Tozawa, T. et al. Porous organic cages. Nat. Mater. 8, 973-978 (2009).
20. Hasell, T. et al. Controlling the crystallization of porous organic cages: molecular analogs of isoreticular frameworks using shape-specific directing solvents. J. Am. Chem. Soc. 136, 1438-1448 (2014).
21. Jones, J. T. A. et al. Modular and predictable assembly of porous organic molecular crystals. Nature 474, 367-371 (2011).
22. Hasell, T., Chong, S. Y., Jelfs, K. E., Adams, D. J. & Cooper, A. I. Porous organic cage nanocrystals by solution mixing. J. Am. Chem. Soc. 134, 588-598 (2012).
23. Unruh, D. K., Gojdas, K., Libo, A. & Forbes, T. Z. Development of metal-organic nanotubes exhibiting low-temperature, reversible exchange of confined ?ice channels?. J. Am. Chem. Soc. 135, 7398-7401 (2013).
24. Hummer, G., Rasaiah, J. C. & Noworyta, J. P. Water conduction through the hydrophobic channel of a carbon nanotube. Nature 414, 188-190 (2001).
25. Ronson, T. K., Zarra, S., Black, S. P. & Nitschke, J. R. Metal-organic container molecules through subcomponent self-assembly. Chem. Commun. 49, 2476-2490 (2013).
26. Xia, Y. N. et al. One-dimensional nanostructures: synthesis, characterization, and applications. Adv. Mater. 15, 353-389 (2003).
27. Herm, Z. R. et al. Separation of hexane isomers in a metal-organic framework with triangular channels. Science 340, 960-964 (2013).
28. He, L. et al. Shape-persistent macrocyclic aromatic tetrasulfonamides: molecules with nanosized cavities and their nanotubular assemblies in solid state. Proc. Natl Acad. Sci. USA 103, 10850-10855 (2006).
29. Liu, Z. et al. Assembly of supramolecular nanotubes from molecular triangles and 1,2-dihalohydrocarbons. J. Am. Chem. Soc. 136, 16651-16660 (2014).
30. 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 366, 324-327 (1993).
31. Wu, X. B. et al. Robust ordered bundles of porous helical nanotubes assembled from fully rigid ionic benzene-1,3,5-tricarboxamides. Chem. Eur. J. 21, 15388-15394 (2015).
32. 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).
33. Frischmann, P. D., Sahli, B. J., Guieu, S., Patrick, B. O. & MacLachlan, M. J. Sterically-limited self-assembly of Pt4 macrocycles into discrete non-covalent nanotubes: porous supramolecular tetramers and hexamers. Chem. Eur. J. 18, 13712-13721 (2012).
34. Ji, Q. et al. Cyclotetrabenzoin: facile synthesis of a shape-persistent molecular square and its assembly into hydrogen-bonded nanotubes. Chem. Eur. J. 21, 17205-17209 (2015).
35. Schneider, M. W. et al. Periphery-substituted [4+6] salicylbisimine cage compounds with exceptionally high surface areas: influence of the molecular structure on nitrogen sorption properties. Chem. Eur. J. 18, 836-847 (2012).
36. Mastalerz, M. & Oppel, I. M. Rational construction of an extrinsic porous molecular crystal with an extraordinary high specific surface area. Angew. Chem. Int. Ed. 51, 5252-5255 (2012).
37. Issa, N., Karamertzanis, P. G., Welch, G. W. A. & Price, S. L. Can the formation of pharmaceutical cocrystals be computationally predicted? I. Comparison of lattice energies. Cryst. Growth Des. 9, 442-453 (2009).
38. Chan, H. C. S., Kendrick, J., Neumann, M. A. & Leusen, F. J. J. Towards ab initio screening of co-crystal formation through lattice energy calculations and crystal structure prediction of nicotinamide, isonicotinamide, picolinamide and paracetamol multi-component crystals. CrystEngComm 15, 3799-3807 (2013).
39. Case, D. H., Campbell, J. E., Bygrave, P. J. & Day, G. M. Convergence properties of crystal structure prediction by quasi-random sampling. J. Chem. Theory Comput. 12, 910-924 (2016).
40. Pyzer-Knapp, E. O. et al. Predicted crystal energy landscapes of porous organic cages. Chem. Sci. 5, 2235-2245 (2014).
41. Cruz-Cabeza, A. J., Day, G. M. & Jones, W. Predicting inclusion behaviour and framework structures in organic crystals. Chem. Eur. J. 15, 13033-13040 (2009).
42. Rodriguez-Albelo, L. M. et al. Zeolitic polyoxometalate-based metal-organic frameworks (Z-POMOFs): computational evaluation of hypothetical polymorphs and the successful targeted synthesis of the redox-active Z-POMOF1. J. Am. Chem. Soc. 131, 16078-16087.
43. Little, M. A. et al. Trapping virtual pores by crystal retro-engineering. Nat. Chem. 7, 153-159 (2015).
44. Marder, S. R., Kippelen, B., Jen, A. K. Y. & Peyghambarian, N. Design and synthesis of chromophores and polymers for electro-optic and photorefractive applications. Nature 388, 845-851 (1997).
45. Dou, J. H. et al. Fine-tuning of crystal packing and charge transport properties of BDOPV derivatives through fluorine substitution. J. Am. Chem. Soc. 137, 15947-15956 (2015).
46. Haddon, R. C. Design of organic metals and superconductors. Nature 256, 394-396 (1975).
47. Coronado, E., Galan-Mascaros, J. R., Gomez-Garc?a, C. J. & Laukhin, V. Coexistence of ferromagnetism and metallic conductivity in a molecule-based layered compound. Nature 408, 447-449 (2000).
48. Crayston, J. A., Devine, J. N. & Walton, J. C. Conceptual and synthetic strategies for the preparation of organic magnets. Tetrahedron 56, 7829-7857 (2000).
49. Weingarten, A. S. et al. Supramolecular packing controls H2 photocatalysis in chromophore amphiphile hydrogels. J. Am. Chem. Soc. 137, 15241-15246 (2015).
50. VandeVondele, J. et al. QUICKSTEP: fast and accurate density functional calculations using a mixed Gaussian and plane waves approach. Comput. Phys. Commun. 167, 103-128 (2005).
51. Perdew, J. P., Burke, K. & Ernzerhof, M. Generalized gradient approximation made simple. Phys. Rev. Lett. 77, 3865-3868 (1996).
52. VandeVondele, J. & Hutter, J. Gaussian basis sets for accurate calculations on molecular systems in gas and condensed phases. J. Chem. Phys. 127, 114105 (2007).
53. Goedecker, S., Teter, M. & Hutter, J. Separable dual-space Gaussian pseudopotentials. Phys. Rev. B 54, 1703-1710 (1996).
54. Grimme, S., Antony, J., Ehrlich, S. & Krieg, H. A consistent and accurate ab initio parametrization of density functional dispersion correction (DFTD) for the 94 elements H-Pu. J. Chem. Phys. 132, 154104 (2010).
55. Childs, H. et al. VisIt: An End-User Tool for Visualizing and Analyzing Very Large Data (Lawrence Livermore National Laboratory, 2012); https://wci.llnl. gov/simulation/computer-codes/visit
56. Price, S. L. et al. Modelling organic crystal structures using distributed multipole and polarizability-based model intermolecular potentials. Phys. Chem. Chem. Phys. 12, 8478-8490 (2010).
57. Chisholm, J. & Motherwell, S. COMPACK: a program for identifying crystal structure similarity using distances. J. Appl. Cryst. 38, 228-231 (2005).
58. Sheldrick, G. Crystal structure refinement with SHELXL. Acta Cryst. C 71, 3-8 (2015).