Moving Beyond Boron: The Emergence of New Linkage Chemistries in Covalent Organic Frameworks

Macromolecules

Volumn 49, Issue 15, 2016, Pages 5297-5305

  Deblase, Catherine R ^a   Dichtel, William R ^a  

^a Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY; MACROMOLECULES;

BORON-CONTAINING; COVALENT ORGANIC FRAMEWORKS; GAS STORAGE; HIGH SURFACE AREA; OXIDATIVE INSTABILITY; POTENTIAL MATERIALS; SOLID-STATE STRUCTURES;

BORON;

EID: 84981267003     PISSN: 00249297     EISSN: 15205835     Source Type: Journal    
DOI: 10.1021/acs.macromol.6b00891     Document Type: Article

References (77)

1. Feng, X.; Ding, X.; Jiang, D. Covalent Organic Frameworks Chem. Soc. Rev. 2012, 41, 6010-6022 10.1039/c2cs35157a
2. Colson, J. W.; Dichtel, W. R. Rationally Synthesized Two-Dimensional Polymers Nat. Chem. 2013, 5, 453-465 10.1038/nchem.1628
3. Ding, S.-Y.; Wang, W. Covalent organic frameworks (COFs): from Design to Applications Chem. Soc. Rev. 2013, 42, 548-568 10.1039/C2CS35072F
4. Côté, A. P.; Benin, A. I.; Ockwig, N. W.; O'Keeffe, M.; Matzger, A. J.; Yaghi, O. M. Porous, Crystalline, Covalent Organic Frameworks Science 2005, 310, 1166-1170 10.1126/science.1120411
5. Spitler, E. L.; Koo, B. T.; Novotney, J. L.; Colson, J. W.; Uribe-Romo, F. J.; Gutierrez, G. D.; Clancy, P.; Dichtel, W. R. A 2D Covalent Organic Framework with 4.7-nm Pores and Insight into Its Interlayer Stacking J. Am. Chem. Soc. 2011, 133, 19416-19421 10.1021/ja206242v
6. Spitler, E. L.; Colson, J. W.; Uribe-Romo, F. J.; Woll, A. R.; Giovino, M. R.; Saldivar, A.; Dichtel, W. R. Lattice Expansion of Highly Oriented 2D Phthalocyanine Covalent Organic Framework Films Angew. Chem., Int. Ed. 2012, 51, 2623-2627 10.1002/anie.201107070
7. Yang, H.; Du, Y.; Wan, S.; Trahan, G. D.; Jin, Y.; Zhang, W. Mesoporous 2D Covalent Organic Frameworks Based on Shape-Persistent Arylene-Ethynylene Macrocycles Chem. Sci. 2015, 6, 4049-4053 10.1039/C5SC00894H
8. Zhu, Y.; Wan, S.; Jin, Y.; Zhang, W. Desymmetrized Vertex Design for the Synthesis of Covalent Organic Frameworks with Periodically Heterogeneous Pore Structures J. Am. Chem. Soc. 2015, 137, 13772-13775 10.1021/jacs.5b09487
9. Dalapati, S.; Addicoat, M.; Jin, S.; Sakurai, T.; Gao, J.; Xu, H.; Irle, S.; Seki, S.; Jiang, D. Rational Design of Crystalline Supermicroporous Covalent Organic Frameworks with Triangular Topologies Nat. Commun. 2015, 6, 7786 10.1038/ncomms8786
10. Nagai, A.; Guo, Z.; Feng, X.; Jin, S.; Chen, X.; Ding, X.; Jiang, D. Pore Surface Engineering in Covalent Organic Frameworks Nat. Commun. 2011, 2, 536 10.1038/ncomms1542
11. DeBlase, C. R.; Silberstein, K. E.; Truong, T.-T.; Abruña, H. D.; Dichtel, W. R. β-Ketoenamine-Linked Covalent Organic Frameworks Capable of Pseudocapacitive Energy Storage J. Am. Chem. Soc. 2013, 135, 16821-16824 10.1021/ja409421d
12. Chandra, S.; Kundu, T.; Kandambeth, S.; BabaRao, R.; Marathe, Y.; Kunjir, S. M.; Banerjee, R. Phosphoric Acid Loaded Azo (-N=N-) Based Covalent Organic Framework for Proton Conduction J. Am. Chem. Soc. 2014, 136, 6570-6573 10.1021/ja502212v
13. Lohse, M. S.; Stassin, T.; Naudin, G.; Wuttke, S.; Ameloot, R.; De Vos, D.; Medina, D. D.; Bein, T. Sequential Pore Wall Modification in a Covalent Organic Framework for Application in Lactic Acid Adsorption Chem. Mater. 2015, 28, 626-631 10.1021/acs.chemmater.5b04388
14. Ding, H.; Li, Y.; Hu, H.; Sun, Y.; Wang, J.; Wang, C.; Wang, C.; Zhang, G.; Wang, B.; Xu, W.; Zhang, D. A Tetrathiafulvalene-Based Electroactive Covalent Organic Framework Chem.-Eur. J. 2014, 20, 14614-14618 10.1002/chem.201405330
15. Xu, F.; Xu, H.; Chen, X.; Wu, D.; Wu, Y.; Liu, H.; Gu, C.; Fu, R.; Jiang, D. Radical Covalent Organic Frameworks: A General Strategy to Immobilize Open-Accessible Polyradicals for High-Performance Capacitive Energy Storage Angew. Chem., Int. Ed. 2015, 54, 6814-6818 10.1002/anie.201501706
16. Bunck, D. N.; Dichtel, W. R. Internal Functionalization of Three-Dimensional Covalent Organic Frameworks Angew. Chem., Int. Ed. 2012, 51, 1885-1889 10.1002/anie.201108462
17. Bunck, D. N.; Dichtel, W. R. Postsynthetic Functionalization of 3D Covalent Organic Frameworks Chem. Commun. 2013, 49, 2457-2459 10.1039/c3cc40358k
18. Brucks, S. D.; Bunck, D. N.; Dichtel, W. R. Functionalization of 3D Covalent Organic Frameworks Using Monofunctional Boronic Acids Polymer 2014, 55, 330-334 10.1016/j.polymer.2013.07.030
19. Huang, N.; Chen, X.; Krishna, R.; Jiang, D. Two-Dimensional Covalent Organic Frameworks for Carbon Dioxide Capture through Channel-Wall Functionalization Angew. Chem., Int. Ed. 2015, 54, 2986-2990 10.1002/anie.201411262
20. Xu, H.; Chen, X.; Gao, J.; Lin, J.; Addicoat, M.; Irle, S.; Jiang, D. Catalytic Covalent Organic Frameworks via Pore Surface Engineering Chem. Commun. 2014, 50, 1292-1294 10.1039/C3CC48813F
21. Huang, N.; Krishna, R.; Jiang, D. Tailor-Made Pore Surface Engineering in Covalent Organic Frameworks: Systematic Functionalization for Performance Screening J. Am. Chem. Soc. 2015, 137, 7079-7082 10.1021/jacs.5b04300
22. Furukawa, H.; Cordova, K. E.; O'Keeffe, M.; Yaghi, O. M. The Chemistry and Applications of Metal-Organic Frameworks Science 2013, 341, 974-986 10.1126/science.1230444
23. Farha, O. K.; Hupp, J. T. Rational Design, Synthesis, Purification, and Activation of Metal-Organic Framework Materials Acc. Chem. Res. 2010, 43, 1166-1175 10.1021/ar1000617
24. McKeown, N. B.; Budd, P. M. Polymers of intrinsic microporosity (PIMs): Organic Materials for Membrane Separations, Heterogeneous Catalysis and Hydrogen Storage Chem. Soc. Rev. 2006, 35, 675-683 10.1039/b600349d
25. Mastalerz, M. Permanent Porous Materials from Discrete Organic Molecules-Towards Ultra-High Surface Areas Chem.-Eur. J. 2012, 18, 10082-10091 10.1002/chem.201201351
26. Tozawa, T.; Jones, J. T. A.; Swamy, S. I.; Jiang, S.; Adams, D. J.; Shakespeare, S.; Clowes, R.; Bradshaw, D.; Hasell, T.; Chong, S. Y.; Tang, C.; Thompson, S.; Parker, J.; Trewin, A.; Bacsa, J.; Slawin, A. M. Z.; Steiner, A.; Cooper, A. I. Porous Organic Cages Nat. Mater. 2009, 8, 973-978 10.1038/nmat2545
27. Zhang, G.; Mastalerz, M. Organic Cage Compounds-from Shape-Persistency to Function Chem. Soc. Rev. 2014, 43, 1934-1947 10.1039/C3CS60358J
28. Tilford, R. W.; Mugavero, S. J.; Pellechia, P. J.; Lavigne, J. J. Tailoring Microporosity in Covalent Organic Frameworks Adv. Mater. 2008, 20, 2741-2746 10.1002/adma.200800030
29. Smith, B. J.; Dichtel, W. R. Mechanistic Studies of Two-Dimensional Covalent Organic Frameworks Rapidly Polymerized from Initially Homogenous Conditions J. Am. Chem. Soc. 2014, 136, 8783-8789 10.1021/ja5037868
30. Du, Y.; Yang, H.; Whiteley, J. M.; Wan, S.; Jin, Y.; Lee, S.-H.; Zhang, W. Ionic Covalent Organic Frameworks with Spiroborate Linkage Angew. Chem., Int. Ed. 2016, 55, 1737-1741 10.1002/anie.201509014
31. Cai, S.-L.; Zhang, Y.-B.; Pun, A. B.; He, B.; Yang, J.; Toma, F. M.; Sharp, I. D.; Yaghi, O. M.; Fan, J.; Zheng, S.-R.; Zhang, W.-G.; Liu, Y. Tunable Electrical Conductivity in Oriented Thin Films of Tetrathiafulvalene-Based Covalent Organic Framework Chem. Sci. 2014, 5, 4693-4700 10.1039/C4SC02593H
32. Jin, S.; Sakurai, T.; Kowalczyk, T.; Dalapati, S.; Xu, F.; Wei, H.; Chen, X.; Gao, J.; Seki, S.; Irle, S.; Jiang, D. Two-Dimensional Tetrathiafulvalene Covalent Organic Frameworks: Towards Latticed Conductive Organic Salts Chem.-Eur. J. 2014, 20, 14608-14613 10.1002/chem.201402844
33. Xu, H.; Tao, S.; Jiang, D. Proton conduction in crystalline and porous covalent organic frameworks Nat. Mater. 2016, 10.1038/nmat4611
34. Ding, S.-Y.; Gao, J.; Wang, Q.; Zhang, Y.; Song, W.-G.; Su, C.-Y.; Wang, W. Construction of Covalent Organic Framework for Catalysis: Pd/COF-LZU1 in Suzuki-Miyaura Coupling Reaction J. Am. Chem. Soc. 2011, 133, 19816-19822 10.1021/ja206846p
35. Guo, J.; Xu, Y.; Jin, S.; Chen, L.; Kaji, T.; Honsho, Y.; Addicoat, M. A.; Kim, J.; Saeki, A.; Ihee, H.; Seki, S.; Irle, S.; Hiramoto, M.; Gao, J.; Jiang, D. Conjugated Organic Framework with Three-Dimensionally Ordered Stable Structure and Delocalized π Clouds Nat. Commun. 2013, 4, 1-8 10.1038/ncomms3736
36. Kandambeth, S.; Mallick, A.; Lukose, B.; Mane, M. V.; Heine, T.; Banerjee, R. Construction of Crystalline 2D Covalent Organic Frameworks with Remarkable Chemical (Acid/Base) Stability via a Combined Reversible and Irreversible Route J. Am. Chem. Soc. 2012, 134, 19524-19527 10.1021/ja308278w
37. Nagai, A.; Chen, X.; Feng, X.; Ding, X.; Guo, Z.; Jiang, D. A Squaraine-Linked Mesoporous Covalent Organic Framework Angew. Chem., Int. Ed. 2013, 52, 3770-3774 10.1002/anie.201300256
38. Kandambeth, S.; Shinde, D. B.; Panda, M. K.; Lukose, B.; Heine, T.; Banerjee, R. Enhancement of Chemical Stability and Crystallinity in Porphyrin-Containing Covalent Organic Frameworks by Intramolecular Hydrogen Bonds Angew. Chem., Int. Ed. 2013, 52, 13052-13056 10.1002/anie.201306775
39. Chen, X.; Addicoat, M.; Jin, E.; Zhai, L.; Xu, H.; Huang, N.; Guo, Z.; Liu, L.; Irle, S.; Jiang, D. Locking Covalent Organic Frameworks with Hydrogen Bonds: General and Remarkable Effects on Crystalline Structure, Physical Properties, and Photochemical Activity J. Am. Chem. Soc. 2015, 137, 3241-3247 10.1021/ja509602c
40. Kuhn, P.; Antonietti, M.; Thomas, A. Porous, Covalent Triazine-Based Frameworks Prepared by Ionothermal Synthesis Angew. Chem., Int. Ed. 2008, 47, 3450-3453 10.1002/anie.200705710
41. Bojdys, M. J.; Jeromenok, J.; Thomas, A.; Antonietti, M. Rational Extension of the Family of Layered, Covalent, Triazine-Based Frameworks with Regular Porosity Adv. Mater. 2010, 22, 2202-2205 10.1002/adma.200903436
42. Ren, S.; Bojdys, M. J.; Dawson, R.; Laybourn, A.; Khimyak, Y. Z.; Adams, D. J.; Cooper, A. I. Porous, Fluorescent, Covalent Triazine-Based Frameworks via Room-Temperature and Microwave-Assisted Synthesis Adv. Mater. 2012, 24, 2357-2361 10.1002/adma.201200751
43. Katekomol, P.; Roeser, J.; Bojdys, M.; Weber, J.; Thomas, A. Covalent Triazine Frameworks Prepared from 1,3,5-Tricyanobenzene Chem. Mater. 2013, 25, 1542-1548 10.1021/cm303751n
44. Liao, H.; Ding, H.; Li, B.; Ai, X.; Wang, C. Covalent Organic Frameworks: Potential Host Materials for Sulfur Impregnation in Lithium-Sulfur Batteries J. Mater. Chem. A 2014, 2, 8854-8858 10.1039/c4ta00523f
45. 2 Capture Energy Environ. Sci. 2013, 6, 3684-3692 10.1039/c3ee42548g
46. Hao, L.; Ning, J.; Luo, B.; Wang, B.; Zhang, Y.; Tang, Z.; Yang, J.; Thomas, A.; Zhi, L. Structural Evolution of 2D Microporous Covalent Triazine-Based Framework toward the Study of High-Performance Supercapacitors J. Am. Chem. Soc. 2015, 137, 219-225 10.1021/ja508693y
47. Uribe-Romo, F. J.; Hunt, J. R.; Furukawa, H.; Klöck, C.; O'Keeffe, M.; Yaghi, O. M. A Crystalline Imine-Linked 3D Porous Covalent Organic Framework J. Am. Chem. Soc. 2009, 131, 4570-4571 10.1021/ja8096256
48. Xu, H.; Gao, J.; Jiang, D. Stable, Crystalline, Porous, Covalent Organic Frameworks as a Platform for Chiral Organocatalysts Nat. Chem. 2015, 7, 905-912 10.1038/nchem.2352
49. 2 Adsorption Chem. Commun. 2015, 51, 10050-10053 10.1039/C5CC02147B
50. 2 Reduction in Water Science 2015, 349, 1208-1213 10.1126/science.aac8343
51. Spitler, E. L.; Dichtel, W. R. Lewis Acid-Catalyzed Formation of Two Dimensional Phtalocyanine Covalent Organic Frameworks Nat. Chem. 2010, 2, 672-677 10.1038/nchem.695
52. Wan, S.; Guo, J.; Kim, J.; Ihee, H.; Jiang, D. A Belt-Shaped, Blue Luminescent, and Semiconducting Covalent Organic Framework Angew. Chem., Int. Ed. 2009, 48, 3207-3207 10.1002/anie.200990092
53. Wan, S.; Gándara, F.; Asano, A.; Furukawa, H.; Saeki, A.; Dey, S. K.; Liao, L.; Ambrogio, M. W.; Botros, Y. Y.; Duan, X.; Seki, S.; Stoddart, J. F.; Yaghi, O. M. Covalent Organic Frameworks with High Charge Carrier Mobility Chem. Mater. 2011, 23, 4094-4097 10.1021/cm201140r
54. Wudl, F.; Southwick, E. W. Tetracyanomuconitritebis(tetrathiafulvalene): the first complex salt of tetrathiafulvalene J. Chem. Soc., Chem. Commun. 1974, 7, 254-255 10.1039/c39740000254
55. Schafer, D. E.; Wudl, F.; Thomas, G. A.; Ferraris, J. P.; Cowan, D. O. Apparent Giant Conductivity Peaks in an Anisotropic Medium: TTF-TCNQ Solid State Commun. 1974, 14, 347-351 10.1016/0038-1098(74)90915-6
56. Feldblyum, J. I.; McCreery, C. H.; Andrews, S. C.; Kurosawa, T.; Santos, E. J. G.; Duong, V.; Fang, L.; Ayzner, A. L.; Bao, Z. Few-Layer, Large-Area, 2D Covalent Organic Framework Semiconductor Thin Films Chem. Commun. 2015, 51, 13894-13897 10.1039/C5CC04679C
57. Biswal, B. P.; Chandra, S.; Kandambeth, S.; Lukose, B.; Heine, T.; Banerjee, R. Mechanochemical Synthesis of Chemically Stable Isoreticular Covalent Organic Frameworks J. Am. Chem. Soc. 2013, 135, 5328-5331 10.1021/ja4017842
58. Das, G.; Shinde, D. B.; Kandambeth, S.; Biswal, B. P.; Banerjee, R. Mechanosynthesis of Imine, β-ketoenamine, and Hydrogen-Bonded Imine-Linked Covalent Organic Frameworks Using Liquid-Assisted Grinding Chem. Commun. 2014, 50, 12615-12618 10.1039/C4CC03389B
59. Jiang, Y.; Huang, W.; Wang, J.; Wu, Q.; Wang, H.; Pan, L.; Liu, X. Green, Scalable and Morphology Controlled Synthesis of Nanofibrous Covalent Organic Frameworks and their Nanohybrids Through a Vapor-Assisted Solid-State Approach J. Mater. Chem. A 2014, 2, 8201-8204 10.1039/c4ta00555d
60. Chandra, S.; Kandambeth, S.; Biswal, B. P.; Lukose, B.; Kunjir, S. M.; Chaudhary, M.; Babarao, R.; Heine, T.; Banerjee, R. Chemically Stable Multilayered Covalent Organic Nanosheets from Covalent Organic Frameworks via Mechanical Delamination J. Am. Chem. Soc. 2013, 135, 17853-17861 10.1021/ja408121p
61. DeBlase, C. R.; Hernández-Burgos, K.; Silberstein, K. E.; Rodríguez-Calero, G. G.; Bisbey, R. P.; Abruña, H. D.; Dichtel, W. R. Rapid and Efficient Redox Processes within 2D Covalent Organic Framework Thin Films ACS Nano 2015, 9, 3178-3183 10.1021/acsnano.5b00184
62. Fang, Q.; Gu, S.; Zheng, J.; Zhuang, Z.; Qiu, S.; Yan, Y. 3D Microporous Base-Functionalized Covalent Organic Frameworks for Size-Selective Catalysts Angew. Chem., Int. Ed. 2014, 53, 2878-2882 10.1002/anie.201310500
63. Thote, J.; Aiyappa, H. B.; Deshpande, A.; Díaz Díaz, D.; Kurungot, S.; Banerjee, R. A Covalent Organic Framework-Cadmium Sulfide Hybrid as a Prototype Photocatalyst for Visible-Light Driven Hydrogen Production Chem.-Eur. J. 2014, 20, 15961-15965 10.1002/chem.201403800
64. Pachfule, P.; Kandambeth, S.; Díaz, D. D.; Banerjee, R. Highly Stable Covalent Organic Framework-Au Nanoparticles Hybrids for Enhanced Activity for Nitrophenol Reduction Chem. Commun. 2014, 50, 3169-3172 10.1039/c3cc49176e
65. Pachfule, P.; Panda, M. K.; Kandambeth, S.; Shivaprasad, S. M.; Díaz, D. D.; Banerjee, R. Multifunctional and Robust Covalent Organic Framework-Nanoparticle Hybrids J. Mater. Chem. A 2014, 2, 7944-7952 10.1039/c4ta00284a
66. Chen, X.; Huang, N.; Gao, J.; Xu, H.; Xu, F.; Jiang, D. Towards Covalent Organic Frameworks with Predesignable and Aligned Open Docking Sites Chem. Commun. 2014, 50, 6161-6163 10.1039/c4cc01825g
67. 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. 2011, 133, 11478-11481 10.1021/ja204728y
68. Bunck, D. N.; Dichtel, W. R. Bulk Synthesis of Exfoliated Two-Dimensional Polymers Using Hydrazone-Linked Covalent Organic Frameworks J. Am. Chem. Soc. 2013, 135, 14952-14955 10.1021/ja408243n
69. Sakamoto, J.; van Heijst, J.; Lukin, O.; Schlüter, A. D. Two-Dimensional Polymers: Just a Dream of Synthetic Chemists? Angew. Chem., Int. Ed. 2009, 48, 1030-1069 10.1002/anie.200801863
70. Stegbauer, L.; Schwinghammer, K.; Lotsch, B. V. A Hydrazone-based Covalent Organic Framework for Photocatalytic Hydrogen Production Chem. Sci. 2014, 5, 2789-2793 10.1039/C4SC00016A
71. Zhang, W.; Jiang, P.; Wang, Y.; Zhang, J.; Zhang, P. Bottom-up Approach to Engineer Two Covalent Porphyrinic Frameworks as Effective Catalysts for Selective Oxidation Catal. Sci. Technol. 2014, 5, 101-104 10.1039/C4CY00969J
72. Zhang, W.; Jiang, P.; Wang, Y.; Zhang, J.; Gao, Y.; Zhang, P. Bottom-up Approach to Engineer a Molybdenum-doped Covalent Organic Framework Catalyst for Selective Oxidation Reaction RSC Adv. 2014, 4, 51544-51547 10.1039/C4RA09304F
73. Li, Z.; Feng, X.; Zou, Y.; Zhang, Y.; Xia, H.; Liu, X.; Mu, Y. A 2D Azine-linked Covalent Organic Framework for Gas Storage Applications Chem. Commun. 2014, 50, 13825-13828 10.1039/C4CC05665E
74. Dalapati, S.; Jin, S.; Gao, J.; Xu, Y.; Nagai, A.; Jiang, D. An Azine-Linked Covalent Organic Framework J. Am. Chem. Soc. 2013, 135, 17310-17313 10.1021/ja4103293
75. Fang, Q.; Zhuang, Z.; Gu, S.; Kaspar, R. B.; Zheng, J.; Wang, J.; Qiu, S.; Yan, Y. Designed Synthesis of Large-Pore Crystalline Polyimide Covalent Organic Frameworks Nat. Commun. 2014, 10.1038/ncomms5503
76. Fang, Q.; Wang, J.; Gu, S.; Kaspar, R. B.; Zhuang, Z.; Zheng, J.; Guo, H.; Qiu, S.; Yan, Y. 3D Porous Crystalline Polyimide Covalent Organic Frameworks for Drug Delivery J. Am. Chem. Soc. 2015, 137, 8352-8355 10.1021/jacs.5b04147
77. Smith, B. J.; Overholts, A. C.; Hwang, N.; Dichtel, W. R. Insight into the crystallization of Amorphous Imine-linked Polymer Networks to 2D Covalent Organic Frameworks Chem. Commun. 2016, 52, 3690-3693 10.1039/C5CC10221A