Gram-scale synthesis of two-dimensional polymer crystals and their structure analysis by X-ray diffraction

Nature Chemistry

Volumn 6, Issue 9, 2014, Pages 779-784

  Kory, Max J ^a   Wörle, Michael ^b   Weber, Thomas ^a   Payamyar, Payam ^a   Van De Poll, Stan W ^a   Dshemuchadse, Julia ^a   Trapp, Nils ^b   Schlüter, A Dieter ^a  

^a ETH ZURICH   (Switzerland)

^b LABORATORY OF INORGANIC CHEMISTRY   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84906567827     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.2007     Document Type: Article

References (30)

1. Schmidt G. M. J. Photodimerization in the solid state. Pure Appl. Chem. 12 647-678 (1971).
2. Wegner G. Topochemical reactions of monomers with conjugated triple bonds. I. Polymerization of 2,4-hexadiyn-1,6-diol derivatives in crystalline state. Z. Naturforsch. 24B 824-832 (1969).
3. Kissel P. et al. A two-dimensional polymer prepared by organic synthesis. Nature Chem. 4 287-291 (2012).
4. Bhola R. et al. A two-dimensional polymer from the anthracene dimer and triptycene motifs. J. Am. Chem. Soc. 135 14134-14140 (2013).
5. Sakamoto J. van Heijst J. Lukin O. & Schlüter A. D. Two-dimensional polymers: just a dream of synthetic chemists? Angew. Chem. Int. Ed. 48 1030-1069 (2009).
6. Colson J. W. & Dichtel W. R. Rationally synthesized two-dimensional polymers. Nature Chem. 5 453-465 (2013).
7. Staudinger H. Concerning polymerization. Ber. Dtsch. Chem. Ges. 53 1073-1085 (1920).
8. Berlanga I. et al. Delamination of layered covalent organic frameworks. Small 7 1207-1211 (2011).
9. Spitler E. L. et al. A 2D covalent organic framework with 4.7-nm pores and insight into its interlayer stacking. J. Am. Chem. Soc. 133 19416-19421(2011).
10. Amo-Ochoa P. et al. Single layers of a multifunctional laminar Cu(I,II) coordination polymer. Chem. Commun. 46 3262-3264 (2010).
11. Li P. Maeda Y. & Xu Q. Top-down fabrication of crystalline metal-organic framework nanosheets. Chem. Commun. 47 8436-8438 (2011).
12. Gallego A. et al. Solvent-induced delamination of a multifunctional two dimensional coordination polymer. Adv. Mater. 25 2141-2146 (2013).
13. Bauer T. et al. Synthesis of free-standing monolayered organometallic sheets at the air/water interface. Angew. Chem. Int. Ed. 50 7879-7884 (2011).
14. Zheng Z. et al. Square-micrometer-sized free-standing organometallic sheets and their square-centimeter-sized multilayers on solid substrates. Macromol. Rapid Commun. 34 1670-1680 (2013).
15. Payamyar P. et al. Synthesis of a covalent monolayer sheet by photochemical anthracene dimerization at the air/water interface and its mechanical characterization by AFM indentation. Adv. Mater. 26 2052-2058 (2014).
16. Bunck D. N. & Dichtel W. R. Bulk synthesis of exfoliated two-dimensional polymers using hydrazone-linked covalent organic frameworks. J. Am. Chem. Soc. 135 14952-14955 (2013).
17. Colson J.W. et al. Oriented 2D covalent organic framework thin films on singlelayer graphene. Science 332 228-231 (2011).
18. Bianco E. et al. Stability and exfoliation of germanane: a germanium graphane analogue. ACS Nano 7 4414-4421 (2013).
19. Kuhn A. Holzmann T. Nuss J. & Lotsch B. V. A facile wet chemistry approach towards unilamellar tin sulfide nanosheets from Li4xSn1-xS2 solid solutions. J. Mater. Chem. A 2 6100-6106 (2014).
20. Xu M. Liang T. Shi M. & Chen H. Graphene-like two dimensional materials. Chem. Rev. 113 3766-3798 (2013).
21. Beaudoin D. Maris T. & Wuest J. D. Constructing monocrystalline covalent organic networks by polymerization. Nature Chem. 5 830-834 (2013).
22. Cote A. P. et al. Porous crystalline covalent organic frameworks. Science 310 1166-1170 (2005).
23. Uribe-Romo F. J. et al. Crystalline covalent organic frameworks with hydrazone linkages. J. Am. Chem. Soc. 133 11478-11481 (2011).
24. Kuhn P. Antonietti M. & Thomas A. Porous covalent triazine-based frameworks prepared by ionothermal synthesis. Angew. Chem. Int. Ed. 47 3450-3453 (2008).
25. Kory M. J. Bergeler M. Reiher M. & Schlüter A. D. Facile synthesis and theoretical conformation analysis of a triazine-based double-decker rotor molecule with three anthracene blades. Chem. Eur. J. 20 6934-6938 (2014).
26. Thomas J. M. Organic reactions in the solid state: accident and design. Pure Appl. Chem. 51 1965-1082 (1979).
27. Hernandez Y. et al. High-yield production of graphene by liquid-phase exfoliation of graphite. Nature Nanotech. 3 563-568 (2008).
28. Ernst K. H. Molecular chirality in surface science. Surf. Sci. 613 1-5 (2013).
29. Bouas-Laurent H. Castellan A. Desvergne J. P. & Lapouyade R. Photodimerization of anthracenes in fluid solutions: (part 2) mechanistic aspects of the photocycloaddition and of the photochemical and thermal cleavage. Chem. Soc. Rev. 30 248-263 (2001).
30. Tomlinson W. J. et al. Reversible photodimerization: a new type of photochromism. Appl. Optics 11 533-548 (1972).