Rationally synthesized two-dimensional polymers

Nature Chemistry

Volumn 5, Issue 6, 2013, Pages 453-465

  Colson, John W ^a   Dichtel, William R ^a  

^a Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYMER;

CHEMISTRY; KINETICS; METHODOLOGY; REVIEW; SURFACE PROPERTY; SYNTHESIS; THERMODYNAMICS;

CHEMISTRY TECHNIQUES, SYNTHETIC; KINETICS; POLYMERS; SURFACE PROPERTIES; THERMODYNAMICS;

MLCS; MLOWN;

EID: 84879109916     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.1628     Document Type: Review

References (126)

1. Bielawski, C. W. & Grubbs, R. H. Living ring-opening metathesis polymerization. Prog. Polym. Sci. 32, 1-29 (2007).
2. Matyjaszewski, K. Atom transfer radical polymerization (ATRP): Current status and future perspectives. Macromolecules 45, 4015-4039 (2012).
3. Matyjaszewski, K. & Tsarevsky, N. V. Nanostructured functional materials prepared by atom transfer radical polymerization. Nature Chem. 1, 276-288 (2009).
4. Semsarilar, M. & Perrier, S. 'Green' reversible addition- fragmentation chain-transfer (RAFT) polymerization. Nature Chem. 2, 811-820 (2010).
5. Dienstmaier, J. F. et al. Synthesis of well-ordered COF monolayers: Surface growth of nanocrystalline precursors versus direct on-surface polycondensation. ACS Nano 5, 9737-9745 (2011).
6. Grill, L. et al. Nano-architectures by covalent assembly of molecular building blocks. Nature Nanotech. 2, 687-691 (2007).
7. Lafferentz, L. et al. Controlling on-surface polymerization by hierarchical and substrate-directed growth. Nature Chem. 4, 215-220 (2012).
8. Zwaneveld, N. A. et al. Organized formation of 2D extended covalent organic frameworks at surfaces. J. Am. Chem. Soc. 130, 6678-6679 (2008).
9. Stupp, S. I., Son, S., Lin, H. C. & Li, L. S. Synthesis of two-dimensional polymers. Science 259, 59-63 (1993).
10. Schultz, M. J. et al. Synthesis of linked carbon monolayers: Films, balloons, tubes, and pleated sheets. Proc. Natl Acad. Sci. USA 105, 7353-7358 (2008).
11. Sakamoto, J., van Heijst, J., Lukin, O. & Schluter, A. D. Two-dimensional polymers: Just a dream of synthetic chemists? Angew. Chem. Int. Ed. 48, 1030-1069 (2009).
12. Kissel, P. et al. A two-dimensional polymer prepared by organic synthesis. Nature Chem. 4, 287-291 (2012).
13. Geim, A. K. & Novoselov, K. S. The rise of graphene. Nature Mater. 6, 183-191 (2007).
14. Whittell, G. R. & Manners, I. Advances with ammonia-borane: Improved recycling and use as a precursor to atomically thin BN films. Angew. Chem. Int. Ed. 50, 10288-10289 (2011).
15. Golberg, D. et al. Boron nitride nanotubes and nanosheets. ACS Nano 4, 2979-2993 (2010).
16. Novoselov, K. S. et al. Two-dimensional atomic crystals. Proc. Natl Acad. Sci. U. S. A. 102, 10451-10453 (2005).
17. Novoselov, K. S. et al. Electric field effect in atomically thin carbon films. Science 306, 666-669 (2004).
18. Berger, C. et al. Electronic confinement and coherence in patterned epitaxial graphene. Science 312, 1191-1196 (2006).
19. Li, X. et al. Large-area synthesis of high-quality and uniform graphene films on copper foils. Science 324, 1312-1314 (2009).
20. Huang, P. Y. et al. Grains and grain boundaries in single-layer graphene atomic patchwork quilts. Nature 469, 389-392 (2011).
21. Chen, L., Hernandez, Y., Feng, X. & Müllen, K. From nanographene and graphene nanoribbons to graphene sheets: Chemical synthesis. Angew. Chem. Int. Ed. 51, 7640-7654 (2012).
22. Pisula, W., Feng, X. & Müllen, K. Charge-carrier transporting graphene-type molecules. Chem. Mater. 23, 554-567 (2011).
23. Simpson, C. D. et al. Synthesis of a giant 222 carbon graphite sheet. Chem. Eur. J. 8, 1424-1429 (2002).
24. Mas-Torrent, M. & Rovira, C. Role of molecular order and solid-state structure in organic field-effect transistors. Chem. Rev. 111, 4833-4856 (2011).
25. Rivnay, J., Mannsfeld, S. C. B., Miller, C. E., Salleo, A. & Toney, M. F. Quantitative determination of organic semiconductor microstructure from the molecular to device scale. Chem. Rev. 112, 5488-5519 (2012).
26. Peet, J., Senatore, M. L., Heeger, A. J. & Bazan, G. C. The role of processing in the fabrication and optimization of plastic solar cells. Adv. Mater. 21, 1521-1527 (2009).
27. Beaujuge, P. M. & Fréchet, J. M. J. Molecular design and ordering effects in functional materials for transistor and solar cell applications. J. Am. Chem. Soc. 133, 20009-20029 (2011).
28. Tsao, H. N. & Müllen, K. Improving polymer transistor performance via morphology control. Chem. Soc. Rev. 39, 2372-2386 (2010).
29. Carlucci, L., Ciani, G., Proserpio, D. M. & Porta, F. Open network architectures from the self-assembly of AgNO3 and 5,10,15,20-tetra(4-pyridyl) porphyrin (H2tpyp) building blocks: The exceptional self-penetrating topology of the 3D network of [Ag8(ZnIItpyp)7(H2O)2](NO3)8. Angew. Chem. Int. Ed. 42, 317-322 (2003).
30. Dai, F., Dou, J., He, H., Zhao, X. & Sun, D. Self-assembly of metal-organic supramolecules: From a metallamacrocycle and a metal-organic coordination cage to 1D or 2D coordination polymers based on flexible dicarboxylate ligands. Inorg. Chem. 49, 4117-4124 (2010).
31. Finke, A. D., Gross, D. E., Han, A. & Moore, J. S. Engineering solid-state morphologies in carbazole-ethynylene macrocycles. J. Am. Chem. Soc. 133, 14063-14070 (2011).
32. Bartels, L. Tailoring molecular layers at metal surfaces. Nature Chem. 2, 87-95 (2010).
33. Lehn, J. M. et al. Spontaneous assembly of double-stranded helicates from oligobipyridine ligands and copper(I) cations: Structure of an inorganic double helix. Proc. Natl. Acad. Sci. USA 84, 2565-2569 (1987).
34. Baxter, P. N. W., Lehn, J.-M., Fischer, J. & Youinou, M.-T. Self-assembly and structure of a 3 × 3 inorganic grid from nine silver ions and six ligand components. Angew. Chem. Int. Ed. Engl. 33, 2284-2287 (1994).
35. Hoskins, B. F. & Robson, R. Infinite polymeric frameworks consisting of three dimensionally linked rod-like segments. J. Am. Chem. Soc. 111, 5962-5964 (1989).
36. Simard, M., Su, D. & Wuest, J. D. Use of hydrogen bonds to control molecular aggregation. Self-assembly of three-dimensional networks with large chambers. J. Am. Chem. Soc. 113, 4696-4698 (1991).
37. Wang, X., Simard, M. & Wuest, J. D. Molecular tectonics. Three-dimensional organic networks with zeolitic properties. J. Am. Chem. Soc. 116, 12119-12120 (1994).
38. Fujita, M., Yazaki, J. & Ogura, K. Preparation of a macrocyclic polynuclear complex, [(en)Pd(4,4′-bpy)]4(NO3)8 (en = ethylenediamine, bpy = bipyridine), which recognizes an organic molecule in aqueous media. J. Am. Chem. Soc. 112, 5645-5647 (1990).
39. Stock, N. & Biswas, S. Synthesis of metal-organic frameworks (MOFs): Routes to various MOF topologies, morphologies, and composites. Chem. Rev. 112, 933-969 (2012).
40. Bae, Y.-S. & Snurr, R. Q. Development and evaluation of porous materials for carbon dioxide separation and capture. Angew. Chem. Int. Ed. 50, 11586-11596 (2011).
41. Zhou, H.-C., Long, J. R. & Yaghi, O. M. Introduction to metal-organic frameworks. Chem. Rev. 112, 673-674 (2012).
42. Bétard, A. & Fischer, R. A. Metal-organic framework thin films: From fundamentals to applications. Chem. Rev. 112, 1055-1083 (2012).
43. Li, J.-R., Sculley, J. & Zhou, H.-C. Metal-organic frameworks for separations. Chem. Rev. 112, 869-932 (2012).
44. Sumida, K. et al. Carbon dioxide capture in metal-organic frameworks. Chem. Rev. 112, 724-781 (2012).
45. Kreno, L. E. et al. Metal-organic framework materials as chemical sensors. Chem. Rev. 112, 1105-1125 (2012).
46. Rowan, S. J., Cantrill, S. J., Cousins, G. R. L., Sanders, J. K. M. & Stoddart, J. F. Dynamic covalent chemistry. Angew. Chem. Int. Ed. 41, 898-952 (2002).
47. Mastalerz, M. Shape-persistent organic cage compounds by dynamic covalent bond formation. Angew. Chem. Int. Ed. 49, 5042-5053 (2010).
48. Jin, Y., Jin, A., McCaffrey, R., Long, H. & Zhang, W. Design strategies for shape-persistent covalent organic polyhedrons (COPs) through imine condensation/metathesis. J. Org. Chem. 77, 7392-7400 (2012).
49. Nishiyabu, R., Kubo, Y., James, T. D. & Fossey, J. S. Boronic acid building blocks: Tools for self assembly. Chem. Commun. 47, 1124-1150 (2011).
50. Hartley, C. S., Elliott, E. L. & Moore, J. S. Covalent assembly of molecular ladders. J. Am. Chem. Soc. 129, 4512-4513 (2007).
51. Hartley, C. S. & Moore, J. S. Programmed dynamic covalent assembly of unsymmetrical macrocycles. J. Am. Chem. Soc. 129, 11682-11683 (2007).
52. Lehn, J.-M. Dynamers: Dynamic molecular and supramolecular polymers. Prog. Polym. Sci. 30, 814-831 (2005).
53. Maeda, T., Otsuka, H. & Takahara, A. Dynamic covalent polymers: Reorganizable polymers with dynamic covalent bonds. Prog. Polym. Sci. 34, 581-604 (2009).
54. Montarnal, D., Capelot, M., Tournilhac, F. & Leibler, L. Silica-like malleable materials from permanent organic networks. Science 334, 965-968 (2011).
55. Côté, A. P. et al. Porous, crystalline, covalent organic frameworks. Science 310, 1166-1170 (2005).
56. Zheng, C. & Zhong, C. Estimation of framework charges in covalent organic frameworks using connectivity-based atom contribution method. J. Phys. Chem. C 114, 9945-9951 (2010).
57. 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).
58. Lukose, B., Kuc, A., Frenzel, J. & Heine, T. On the reticular construction concept of covalent organic frameworks. Beilstein J. Nanotechnol. 1, 60-70 (2010).
59. Lukose, B., Kuc, A. & Heine, T. The structure of layered covalent-organic frameworks. Chem. Eur. J. 17, 2388-2392 (2010).
60. Zhou, W., Wu, H. & Yildirim, T. Structural stability and elastic properties of prototypical covalent organic frameworks. Chem. Phys. Lett. 499, 103-107 (2010).
61. Koo, B. T., Dichtel, W. R. & Clancy, P. A classification scheme for the stacking of two-dimensional boronate ester-linked covalent organic frameworks. J. Mater. Chem. 22, 17460-17469 (2012).
62. Chen, X., Addicoat, M., Irle, S., Nagai, A. & Jiang, D. Control of crystallinity and porosity of covalent organic frameworks by managing interlayer interactions based on self-complementary electronic force. J. Am. Chem. Soc. 135, 546-549 (2013).
63. El-Kaderi, H. M. et al. Designed synthesis of 3D covalent organic frameworks. Science 316, 268-272 (2007).
64. Hunt, J. R., Doonan, C. J., LeVangie, J. D., Côté, A. P. & Yaghi, O. M. Reticular synthesis of covalent organic borosilicate frameworks. J. Am. Chem. Soc. 130, 11872-11873 (2008).
65. Bunck, D. N. & Dichtel, W. R. Internal functionalization of three-dimensional covalent organic frameworks. Angew. Chem. Int. Ed. 51, 1885-1889 (2012).
66. Yu, J.-T., Chen, Z., Sun, J., Huang, Z.-T. & Zheng, Q.-Y. Cyclotricatechylene based porous crystalline material: Synthesis and applications in gas storage. J. Mater. Chem. 22, 5369-5373 (2012).
67. Kahveci, Z., Islamoglu, T., Shar, G. A., Ding, R. & El-Kaderi, H. M. Targeted synthesis of a mesoporous triptycene-derived covalent organic framework. Cryst Eng Comm 15, 1524-1527 (2013).
68. Côté, A. P., El-Kaderi, H. M., Furukawa, H., Hunt, J. R. & Yaghi, O. M. Reticular synthesis of microporous and mesoporous 2D covalent organic frameworks. J. Am. Chem. Soc. 129, 12914-12915 (2007).
69. Wan, S., Guo, J., Kim, J., Ihee, H. & Jiang, D. A belt-shaped, blue luminescent, and semiconducting covalent organic framework. Angew. Chem. Int. Ed. 47, 8826-8830 (2008).
70. Nagai, A. et al. Pore surface engineering in covalent organic frameworks. Nature Commun. 2, 1-8 (2011).
71. Du, Y. et al. Experimental and computational studies of pyridine-assisted post-synthesis modified air stable covalent-organic frameworks. Chem. Commun. 48, 4606-4608 (2012).
72. Ding, X. et al. Synthesis of metallophthalocyanine covalent organic frameworks that exhibit high carrier mobility and photoconductivity. Angew. Chem. Int. Ed. 50, 1289-1293 (2011).
73. Spitler, E. L. & Dichtel, W. R. Lewis acid-catalysed formation of two-dimensional phthalocyanine covalent organic frameworks. Nature Chem. 2, 672-677 (2010).
74. Ding, X. et al. An n-channel two-dimensional covalent organic framework. J. Am. Chem. Soc. 133, 14510-14513 (2011).
75. Feng, X., Chen, L., Dong, Y. & Jiang, D. Porphyrin-based two-dimensional covalent organic frameworks: Synchronized synthetic control of macroscopic structures and pore parameters. Chem. Commun. 47, 1979-1981 (2011).
76. Tilford, R. W., Gemmill, W. R., zur Loye, H.-C. & Lavigne, J. J. Facile synthesis of a highly crystalline, covalently linked porous boronate network. Chem. Mater. 18, 5296-5301 (2006).
77. Tilford, R. W., Mugavero, S. J., Pellechia, P. J. & Lavigne, J. J. Tailoring microporosity in covalent organic frameworks. Adv. Mater. 20, 2741-2746 (2008).
78. Lanni, L. M., Tilford, R. W., Bharathy, M. & Lavigne, J. J. Enhanced hydrolytic stability of self-assembling alkylated two-dimensional covalent organic frameworks. J. Am. Chem. Soc. 133, 13975-13983 (2011).
79. Spitler, E. L., Giovino, M. R., White, S. L. & Dichtel, W. R. A mechanistic study of Lewis acid-catalyzed covalent organic framework formation. Chem. Sci. 2, 1588-1593 (2011).
80. Feng, X., Dong, Y. & Jiang, D. Star-shaped two-dimensional covalent organic frameworks. Cryst Eng Comm 15, 1508-1511 (2013).
81. Dogru, M. et al. Facile synthesis of a mesoporous benzothiadiazole-COF based on a transesterification process. Cryst Eng Comm 15, 1500-1502 (2013).
82. Rabbani, M. G. et al. A 2D mesoporous imine-linked covalent organic framework for high pressure gas storage applications. Chem. Eur. J. 19, 3324-3328 (2013).
83. Kuhn, P., Antonietti, M. & Thomas, A. Porous, covalent triazine-based frameworks prepared by ionothermal synthesis. Angew. Chem. Int. Ed. 47, 3450-3453 (2008).
84. Ding, S. Y. et al. Construction of covalent organic framework for catalysis: Pd/COF-LZU1 in Suzuki-Miyaura coupling reaction. J. Am. Chem. Soc. 133, 19816-19822 (2011).
85. Uribe-Romo, F. J., Doonan, C. J., Furukawa, H., Oisaki, K. & Yaghi, O. M. Crystalline covalent organic frameworks with hydrazone linkages. J. Am. Chem. Soc. 133, 11478-11481 (2011).
86. Kandambeth, S. et al. Construction of crystalline 2D covalent organic frameworks with remarkable chemical (acid/base) stability via a combined reversible and irreversible route. J. Am. Chem. Soc. 134, 19524-19527 (2012).
87. Jackson, K. T., Reich, T. E. & El-Kaderi, H. M. Targeted synthesis of a porous borazine-linked covalent organic framework. Chem. Commun. 48, 8823-8825 (2012).
88. Han, S. S., Furukawa, H., Yaghi, O. M. & Goddard, W. A. III Covalent organic frameworks as exceptional hydrogen storage materials. J. Am. Chem. Soc. 130, 11580-11581 (2008).
89. Furukawa, H. & Yaghi, O. M. Storage of hydrogen, methane, and carbon dioxide in highly porous covalent organic frameworks for clean energy applications. J. Am. Chem. Soc. 131, 8875-8883 (2009).
90. Doonan, C. J., Tranchemontagne, D. J., Glover, T. G., Hunt, J. R. & Yaghi, O. M. Exceptional ammonia uptake by a covalent organic framework. Nature Chem. 2, 235-238 (2010).
91. Benanti, T. & Venkataraman, D. Organic solar cells: An overview focusing on active layer morphology. Photosynth. Res. 87, 73-81 (2006).
92. Wan, S., Guo, J., Kim, J., Ihee, H. & Jiang, D. A photoconductive covalent organic framework: Self-condensed arene cubes composed of eclipsed 2D polypyrene sheets for photocurrent generation. Angew. Chem. Int. Ed. 48, 5439-5442 (2009).
93. Wan, S. et al. Covalent organic frameworks with high charge carrier mobility. Chem. Mater. 23, 4094-4097 (2011).
94. Jin, S. et al. Charge dynamics in a donor-acceptor covalent organic framework with periodically ordered bicontinuous heterojunctions. Angew. Chem. Int. Ed. 52, 2017-2021 (2013).
95. Dogru, M. et al. A photoconductive thienothiophene-based covalent organic framework showing charge transfer towards included fullerene. Angew. Chem. Int. Ed. 52, 2920-2924 (2013).
96. Patwardhan, S., Kocherzhenko, A. A., Grozema, F. C. & Siebbeles, L. D. A. Delocalization and mobility of charge carriers in covalent organic frameworks. J. Phys. Chem. C 115, 11768-11772 (2011).
97. Senthilkumar, K., Grozema, F. C., Bickelhaupt, F. M. & Siebbeles, L. D. A. Charge transport in columnar stacked triphenylenes: Effects of conformational fluctuations on charge transfer integrals and site energies. J. Chem. Phys. 119, 9809-9817 (2003).
98. Spitler, E. L. et al. Lattice expansion of highly oriented 2D phthalocyanine covalent organic framework films. Angew. Chem. Int. Ed. 51, 2623-2627 (2012).
99. Dogru, M., Sonnauer, A., Gavryushin, A., Knochel, P. & Bein, T. A covalent organic framework with 4 nm open pores. Chem. Commun. 47, 1707-1709 (2011).
100. Feng, X. et al. High-rate charge-carrier transport in porphyrin covalent organic frameworks: Switching from hole to electron to ambipolar conduction. Angew. Chem. Int. Ed. 51, 2618-2622 (2012).
101. Feng, X. et al. An ambipolar conducting covalent organic framework with self-sorted and periodic electron donor-acceptor ordering. Adv. Mater. 24, 3026-3031 (2012).
102. Colson, J. W. et al. Oriented 2D covalent organic framework thin films on single-layer graphene. Science 332, 228-231 (2011).
103. Pang, S., Hernandez, Y., Feng, X. & Müllen, K. Graphene as transparent electrode material for organic electronics. Adv. Mater. 23, 2779-2795 (2011).
104. Berlanga, I. et al. Delamination of layered covalent organic frameworks. Small 7, 1207-1211 (2011).
105. Clair, S., Ourdjini, O., Abel, M. & Porte, L. Two-dimensional polymer as a mask for surface nanopatterning. Adv. Mater. 24, 1252-1254 (2012).
106. Gutzler, R. et al. Surface mediated synthesis of 2D covalent organic frameworks: 1,3,5-tris(4-bromophenyl)benzene on graphite(001), Cu(111), and Ag(110). Chem. Commun. 45, 4456-4458 (2009).
107. Ourdjini, O. et al. Substrate-mediated ordering and defect analysis of a surface covalent organic framework. Phys. Rev. B 84, 125421-125429 (2011).
108. Marele, A. C. et al. Formation of a surface covalent organic framework based on polyester condensation. Chem. Commun. 48, 6779-6781 (2012).
109. Faury, T. et al. Sequential linking to control growth of a surface covalent organic framework. J. Phys. Chem. C 116, 4819-4823 (2012).
110. Dienstmaier, J. F. et al. Isoreticular two-dimensional covalent organic frameworks synthesized by on-surface condensation of diboronic acids. ACS Nano 6, 7234-7242 (2012).
111. Guan, C. Z., Wang, D. & Wan, L. J. Construction and repair of highly ordered 2D covalent networks by chemical equilibrium regulation. Chem. Commun. 48, 2943-2945 (2012).
112. Slater, A. G., Beton, P. H. & Champness, N. R. Two-dimensional supramolecular chemistry on surfaces. Chem. Sci. 2, 1440-1448 (2011).
113. Lipton-Duffin, J. A., Ivasenko, O., Perepichka, D. F. & Rosei, F. Synthesis of polyphenylene molecular wires by surface-confined polymerization. Small 5, 592-597 (2009).
114. Lipton-Duffin, J. A. et al. Step-by-step growth of epitaxially aligned polythiophene by surface-confined reaction. Proc. Natl Acad. Sci. USA 107, 11200-11204 (2010).
115. Lafferentz, L. et al. Conductance of a single conjugated polymer as a continuous function of its length. Science 323, 1193-1197 (2009).
116. Cai, J. et al. Atomically precise bottom-up fabrication of graphene nanoribbons. Nature 466, 470-473 (2010).
117. Abel, M., Clair, S., Ourdjini, O., Mossoyan, M. & Porte, L. Single layer of polymeric Fe-phthalocyanine: An organometallic sheet on metal and thin insulating film. J. Am. Chem. Soc. 133, 1203-1205 (2011).
118. Bieri, M. et al. Two-dimensional polymer formation on surfaces: Insight into the roles of precursor mobility and reactivity. J. Am. Chem. Soc. 132, 16669-16676 (2010).
119. Treier, M., Richardson, N. V. & Fasel, R. Fabrication of surface-supported low-dimensional polyimide networks. J. Am. Chem. Soc. 130, 14054-14055 (2008).
120. Weigelt, S. et al. Surface synthesis of 2D branched polymer nanostructures. Angew. Chem. Int. Ed. 47, 4406-4410 (2008).
121. Jensen, S., Früchtl, H. & Baddeley, C. J. Coupling of triamines with diisocyanates on Au(111) leads to the formation of polyurea networks. J. Am. Chem. Soc. 131, 16706-16713 (2009).
122. Blunt, M. O., Russell, J. C., Champness, N. R. & Beton, P. H. Templating molecular adsorption using a covalent organic framework. Chem. Commun. 46, 7157-7159 (2010).
123. Ozaki, H. et al. Formation of atomic cloth observed by penning ionization electron spectroscopy. J. Chem. Phys. 103, 1226-1228 (1995).
124. Takami, T. et al. Periodic structure of a single sheet of a clothlike macromolecule (atomic cloth) studied by scanning tunneling microscopy. Angew. Chem. Int. Ed. Engl. 36, 2755-2757 (1997).
125. Miura, A. et al. Light-and STM-tip-induced formation of one-dimensional and two-dimensional organic nanostructures. Langmuir 19, 6474-6482 (2003).
126. Okawa, Y. & Aono, M. Nanoscale control of chain polymerization. Nature 409, 683-684 (2001).