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Construction of Crystalline 2D Covalent Organic Frameworks with Remarkable Chemical (Acid/Base) Stability via a Combined Reversible and Irreversible Route
Abstract
Two new chemically stable [acid and base] 2D crystalline covalent organic frameworks (COFs) (TpPa-1 and TpPa-2) were synthesized using combined reversible and irreversible organic reactions. Syntheses of these COFs were done by the Schiff base reactions of 1,3,5-triformylphloroglucinol (Tp) with p-phenylenediamine (Pa-1) and 2,5-dimethyl-p-phenylenediamine (Pa-2), respectively, in 1:1 mesitylene/dioxane. The expected enol-imine (OH) form underwent irreversible proton tautomerism, and only the keto-enamine form was observed. Because of the irreversible nature of the total reaction and the absence of an imine bond in the system, TpPa-1 and TpPa-2 showed strong resistance toward acid (9 N HCl) and boiling water. Moreover, TpPa-2 showed exceptional stability in base (9 N NaOH) as well.
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Cited by
Stable, crystalline, porous, covalent organic frameworks as a platform for chiral organocatalysts
Xu, H., Gao, J., & Jiang, D. (2015) · Nature Chemistry · doi:10.1038/nchem.2352 · Cited by 1,643
Sulfone-containing covalent organic frameworks for photocatalytic hydrogen evolution from water
Wang, X., Chen, L., Chong, S. Y., Little, M. A., Wu, Y., Zhu, W.-H., Clowes, R., Yan, Y., Zwijnenburg, M. A., Sprick, R. S., et al. (2018) · Nature Chemistry · doi:10.1038/s41557-018-0141-5 · Cited by 1,320
Covalent Organic Framework Photocatalysts: Structures and Applications
Wang, H., Wang, H., Wang, Z., Tang, L., Zeng, G., Xu, P., Chen, M., Xiong, T., Zhou, C., Li, X., et al. (2020) · Chemical Society Reviews · doi:10.1039/d0cs00278j · Cited by 1,301
Wang, H., Zeng, Z., Xu, P., Li, L., Zeng, G., Xiao, R., Tang, Z., Huang, D., Tang, L., Lai, C., et al. (2019) · Chemical Society Reviews · doi:10.1039/c8cs00376a · Cited by 804
Closed-loop recycling of plastics enabled by dynamic covalent diketoenamine bonds
Christensen, P. R., Scheuermann, A. M., Loeffler, K. E., & Helms, B. A. (2019) · Nature Chemistry · doi:10.1038/s41557-019-0249-2 · Cited by 676
Metadata
- Authors
- Kandambeth, S., Mallick, A., Lukose, B., Mane, M. V., Heine, T., & Banerjee, R.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2012-11-20
- Volume
- 134
- Issue
- 48
- Pages
- 19524-19527
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2050571756
- Cited by
- 2,156
- References
- 0
- FWCI
- 15.06
- Type
- journal article
- Language
- en
- Open access
- closed
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- Kandambeth, S., Mallick, A., Lukose, B., Mane, M. V., Heine, T., & Banerjee, R. (2012). Construction of Crystalline 2D Covalent Organic Frameworks with Remarkable Chemical (Acid/Base) Stability via a Combined Reversible and Irreversible Route. Journal of the American Chemical Society. https://doi.org/10.1021/ja308278w
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