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Chemical Conversion of Linkages in Covalent Organic Frameworks
Open accessAbstract
The imine linkages of two layered, porous covalent organic frameworks (COFs), TPB-TP-COF ([C 6 H 3 (C 6 H 4 N) 3 ] 2 [C 6 H 4 (CH) 2 ] 3, 1 ) and 4PE-1P-COF ([C 2 (C 6 H 4 N) 4 ][C 6 H 4 (CH) 2 ] 2, 2 ), have been transformed into amide linkages to make the respective isostructural amide COFs 1′ and 2′ by direct oxidation with retention of crystallinity and permanent porosity. Remarkably, the oxidation of both imine COFs is complete, as assessed by FT-IR and 13 C CP-MAS NMR spectroscopy and demonstrates (a) the first chemical conversion of a COF linkage and (b) how the usual “crystallization problem” encountered in COF chemistry can be bypassed to access COFs, such as these amides, that are typically thought to be difficult to obtain by the usual de novo methods. The amide COFs show improved chemical stability relative to their imine progenitors.
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Cited by
Liu, R., Tan, K. T., Gong, Y., Chen, Y., Li, Z., Xie, S., He, T., Lu, Z., Yang, H., & Jiang, D. (2021) · Chemical Society Reviews · doi:10.1039/d0cs00620c · Cited by 1,083
Beuerle, F., & Gole, B. (2018) · Angewandte Chemie International Edition · doi:10.1002/anie.201710190 · Cited by 528
Polymer Networks: From Plastics and Gels to Porous Frameworks
Gu, Y., Zhao, J., & Johnson, J. A. (2020) · Angewandte Chemie International Edition · doi:10.1002/anie.201902900 · Cited by 388
Yang, J., Ghosh, S., Roeser, J., Acharjya, A., Penschke, C., Tsutsui, Y., Rabeah, J., Wang, T., Djoko Tameu, S. Y., Ye, M.-Y., et al. (2022) · Nature Communications · doi:10.1038/s41467-022-33875-9 · Cited by 279
Metadata
- Authors
- Waller, P. J., Lyle, S. J., Osborn Popp, T. M., Diercks, C. S., Reimer, J. A., & Yaghi, O. M.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2016-11-29
- Volume
- 138
- Issue
- 48
- Pages
- 15519-15522
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2551020416
- Cited by
- 604
- References
- 0
- FWCI
- 15.86
- Type
- journal article
- Language
- en
- Open access
- green
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- Waller, P. J., Lyle, S. J., Osborn Popp, T. M., Diercks, C. S., Reimer, J. A., & Yaghi, O. M. (2016). Chemical Conversion of Linkages in Covalent Organic Frameworks. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.6b08377
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