Abstract
Metal-organic Frameworks (MOF) are a new class of functional crystalline materials with the large nanopores and open frame structures. The controlled nanoporous structures attract for various applications such as gas sorption, catalysis, biomedical applications, and transport materials for electronic and photophysical devices. For the large demands on preparing the advanced functional materials based on the MOF, the functionalization of the MOF has been attracted significant attention for controlling the environments of the nanopores in the past decade. Among them, the most fruitful approach is post-synthetic modification (PSM) of the MOF.The PSM is defined as the modification of the organic ligands in the frameworks of the MOF by chemical reactions, especially organic reactions, after the formation of the MOF as crystalline materials. In this review, we focus the PSM of the MOF by copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) and the related reactions that have many advantages such as diverse substrates, mild conditions, high yields, high 1,4-regio-selectivity, and high orthogonality for other organic reactions, and wide availability of the media. Furthermore, we discuss the control of the functions of the MOF and the preparation of the functional composites based on the MOF by the CuAAC of the MOF. Therefore, this review includes the following four topics: the exploration of CuAAC reaction for PSM in MOF, the development of other click reactions for PSM, the function-oriented PSM by CuAAC reaction, and networking and biocongujation of MOF.
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References
Kitagawa, S., Kitaura, R., Noro, S.: Functional Porous Coordination Polymers. Angew. Chem. Int. Ed. 43, 2334–2375 (2004)
Stock, N., Biswas, S.: synthesis of metal-organic frameworks (MOFs): routes to various MOF topologies, morphologies, and composites. Chem. Rev. 112, 933–969 (2012)
Furukawa, H., Cordova, K.E., O’Keeffe, M., Yaghi, O.M.: The chemistry and applications of metal-organic frameworks. Science 341, 1230444 (2013)
Suh, M.P., Park, H.J., Prasad, T.K., Lim, D.-W.: Hydrogen storage in metal-organic frameworks. Chem. Rev. 112, 782–835 (2012)
Murray, L.J., Dincă, M., Long, J.R.: Hydrogen storage in metal–organic frameworks. Chem. Soc. Rev. 38, 1294–1314 (2009)
Corma, A., García, H., Llabrés i Xamena, F.X.: Engineering metal organic frameworks for heterogeneous catalysis. Chem. Rev. 110, 4606–4655 (2010)
Yoon, M., Srirambalaji, R., Kim, K.: Homochiral metal-organic frameworks for asymmetric heterogeneous catalysis. Chem. Rev. 112, 1196–1231 (2012)
Farrusseng, D., Aguado, S., Pinel, C.: Metal-Organic frameworks: opportunities for catalysis. Angew. Chem. Int. Ed. 48, 7502–7513 (2009)
Della Rocca, J., Liu, D., Lin, W.: Nanoscale metal–organic frameworks for biomedical imaging and drug delivery. Acc. Chem. Res. 44, 957–968 (2011)
Horcajada, P., Gref, R., Baati, T., Allan, P.K., Maurin, G., Couvreur, P., Férey, G., Morris, R.E., Serre, C.: Metal-organic frameworks in biomedicine. Chem. Rev. 112, 1232–1268 (2012)
Stavila, V., Talin, A.A., Allendorf, M.D.: MOF-based electronic and optoelectronic devices. Chem. Soc. Rev. 43, 5994–6010 (2014)
Hu, Z., Deibert, B.J., Li, J.: Luminescent metal-organic frameworks for chemical sensing and explosive detection. Chem. Soc. Rev. 43, 5815–5840 (2014)
Férey, G.: Hybrid porous solids: Past, present, future. Chem. Soc. Rev. 37, 191–214 (2008)
Kuppler, R.J., Timmons, D.J., Fang, Q.-R., Li, J.-R., Makal, T.A., Young, M.D., Yuan, D., Zhao, D., Zhuang, W., Zhou, H.-C.: Potential applications of metal-organic frameworks. Coord. Chem. Rev. 253, 3042–3066 (2009)
Cohen, S.M.: Postsynthetic methods for the functionalization of metal-organic frameworks. Chem. Rev. 112, 970–1000 (2012)
Cohen, S.M.: The postsynthetic renaissance in porous solids. J. Am. Chem. Soc. 139, 2855–2863 (2017)
Tanabe, K.K., Cohen, S.M.: Postsynthetic modification of metal-organic frameworks—A progress report. Chem. Soc. Rev. 40, 498–519 (2011)
Wang, Z., Cohen, S.M.: Postsynthetic covalent modification of a neutral metal-organic framework. J. Am. Chem Soc. 129, 12368–12369 (2007)
Rostovtsev, V.V., Green, L.G., Fokin, V.V., Sharpless, K.B.: A stepwise huisgen cycloaddition process: Copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes. Angew. Chem. Int. Ed. 41, 2596–2599 (2002)
Kolb, H.C., Finn, M.G., Sharpless, K.B.: Click chemistry: Diverse chemical function from a few good reactions. Angew. Chemie Int. Ed. 40, 2004–2021 (2001)
Wang, C., Ikhlef, D., Kahlal, S., Saillard, J.-Y., Astruc, D.: Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends. Coord. Chem. Rev. 316, 1–20 (2016)
Liang, L., Astruc, D.: The copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) “click” reaction and its applications. An overview. Coord. Chem. Rev. 255, 2933–2945 (2011)
Binder, W.H., Sachsenhofer, R.: “Click” chemistry in polymer and materials science. Macromol. Rapid Commun. 28, 15–54 (2007)
Doehler, D., Michael, P., Binder, W.H.: CuAAC-based click chemistry in self-healing polymers. Acc. Chem. Res. 50, 2610–2620 (2017)
Li, P.-Z., Wang, X.-J., Zhao, Y.: Click chemistry as a versatile reaction for construction and modification of metal-organic frameworks. Coord. Chem. Rev. 380, 484–518 (2019)
Goto, Y., Sato, H., Shinkai, S., Sada, K.: “Clickable” metal-organic framework. J. Am. Chem. Soc. 130, 14354–14355 (2008)
Gadzikwa, T., Lu, G., Stern, C.L., Wilson, S.R., Hupp, J.T., Nguyen, S.T.: Covalent surface modification of a metal-organic framework: Selective surface engineering via Cu I-catalyzed Huisgen cycloaddition, Chem. Commun., 5493–5495 (2008)
Gadzikwa, T., Farha, O.K., Malliakas, C.D., Kanatzidis, M.G., Hupp, J.T., Nguyen, S.T.: Selective bifunctional modification of a non-catenated metal-organic framework material via “click” chemistry. J. Am. Chem. Soc. 131, 13613–13615 (2009)
Savonnet, M., Bazer-Bachi, D., Bats, N., Perez-Pellitero, J., Jeanneau, E., Lecocq, V., Pinel, C., Farrusseng, D.: Generic postfunctionalization route from amino-derived metal-organic frameworks. J. Am. Chem. Soc. 132, 4518–4519 (2010)
Tuci, G., Rossin, A., Xu, X., Ranocchiari, M., van Bokhoven, J.A., Luconi, L., Manet, I., Melucci, M., Giambastiani, G.: “Click” on MOFs: A versatile tool for the multimodal derivatization of N-3-Decorated metal organic frameworks. Chem. Mater. 25, 2297–2308 (2013)
Agard, N.J., Prescher, J.A., Bertozzi, C.R.: A strain-promoted [3 + 2] azide − alkyne cycloaddition for covalent modification of biomolecules in living systems. J. Am. Chem. Soc. 126, 15046–15047 (2004)
Sletten, E.M., Bertozzi, C.R.: Bioorthogonal chemistry: Fishing for selectivity in a sea of functionality. Angew. Chem. Int. Ed. 48, 6974–6998 (2009)
Liu, C., Li, T., Rosi, N.L.: Strain-promoted “click” modification of a mesoporous metal-organic framework. J. Am. Chem. Soc. 134, 18886–18888 (2012)
Wang, Z., Liu, J., Arslan, H.K., Grosjean, S., Hagendorn, T., Gliemann, H., Braese, S., Woell, C.: post-synthetic modification of metal-organic framework thin films using click chemistry: the importance of strained C-C triple bonds. Langmuir 29, 15958–15964 (2013)
Chen, C., Allen, C.A., Cohen, S.M.: tandem postsynthetic modification of metal-organic frameworks using an inverse-electron-demand diels-alder reaction. Inorg. Chem. 50, 10534–10536 (2011)
Hindelang, K., Kronast, A., Vagin, S.I., Rieger, B.: Functionalization of metal-organic frameworks through the postsynthetic transformation of olefin side groups. Chem. Eur. J. 19, 8244–8252 (2013)
Jiang, H.-L., Feng, D., Liu, T.-F., Li, J.-R., Zhou, H.-C.: Pore surface engineering with controlled loadings of functional groups via click chemistry in highly stable metal-organic frameworks. J. Am. Chem. Soc. 134, 14690–14693 (2012)
Li, P.Z., Wang, X.J., Tan, R.H.D., Zhang, Q., Zou, R., Zhao, Y.: Rationally “clicked” post-modification of a highly stable metal-organic framework and its high improvement on CO2-selective capture. RSC Adv. 3, 15566–15570 (2013)
Deria, P., Bury, W., Hupp, J.T., Farha, O.K.: Versatile functionalization of the NU-1000 platform by solvent-assisted ligand incorporation. Chem. Commun. 50, 1965–1968 (2014)
Li, B., Gui, B., Hu, G., Yuan, D., Wang, C.: postsynthetic modification of an alkyne-tagged zirconium metal-organic framework via a “click” reaction. Inorg. Chem. 54, 5139–5141 (2015)
Savonnet, M., Camarata, A., Canivet, J., Bazer-Bachi, D., Bats, N., Lecocq, V., Pinel, C., Farrusseng, D.: Tailoring metal-organic framework catalysts by click chemistry. Dalt. Trans. 41, 3945–3948 (2012)
Zhu, W., He, C., Wu, P., Wu, X., Duan, C.: “Click” post-synthetic modification of metal-organic frameworks with chiral functional adduct for heterogeneous asymmetric catalysis. Dalt. Trans. 41, 3072–3077 (2012)
Yi, X.C., Xi, F.G., Qi, Y., Gao, E.Q.: Synthesis and click modification of an azido-functionalized Zr(IV) metal-organic framework and a catalytic study. RSC Adv. 5, 893–900 (2015)
Ishiwata, T., Furukawa, Y., Sugikawa, K., Kokado, K., Sada, K.: Transformation of metal-organic framework to polymer gel by cross-linking the organic ligands preorganized in metal-organic framework. J. Am. Chem. Soc. 135, 5427–5432 (2013)
Ishiwata, T., Kokado, K., Sada, K.: Anisotropically swelling gels attained through axis-dependent crosslinking of mof crystals. Angew. Chem. Int. Ed. 56, 2608–2612 (2017)
Ishiwata, T., Michibata, A., Kokado, K., Ferlay, S., Hosseini, M.W., Sada, K.: Box-like gel capsules from heterostructures based on a core–shell MOF as a template of crystal crosslinking. Chem. Commun. 54, 1437–1440 (2018)
Anan, S., Mochizuki, Y., Kokado, K., Sada, K.: step-growth copolymerization between an immobilized monomer and a mobile monomer in metal-organic frameworks. Angew. Chem. Int. Ed. 58, 8018–8023 (2019)
Zhou, W., Begum, S., Wang, Z., Krolla, P., Wagner, D., Braese, S., Woell, C., Tsotsalas, M.: High antimicrobial activity of metal-organic framework-templated porphyrin polymer thin films. ACS Appl. Mater. Interfaces. 10, 1528–1533 (2018)
Lindemann, P., Tsotsalas, M., Shishatskiy, S., Abetz, V., Krolla-Sidenstein, P., Azucena, C., Monnereau, L., Beyer, A., Goelzhaeuser, A., Mugnaini, V., Gliemann, H., Braese, S., Woell, C.: Preparation of freestanding conjugated microporous polymer nanomembranes for gas separation. Chem. Mater. 26, 7189–7193 (2014)
Wang, Z., Blaszczyk, A., Fuhr, O., Heissler, S., Woell, C., Mayor, M.: Molecular weaving via surface-templated epitaxy of crystalline coordination networks. Nat. Commun. 8, 14442 (2017)
Morris, W., Briley, W.E., Auyeung, E., Cabezas, M.D., Mirkin, C.A.: Nucleic acid-metal organic framework (MOF) nanoparticle conjugates. J. Am. Chem. Soc. 136, 7261–7264 (2014)
Kahn, J.S., Freage, L., Enkin, N., Garcia, M.A.A., Willner, I.: stimuli-responsive DNA-functionalized metal-organic frameworks (MOFs). Adv. Mater. 29, 1602782 (2017)
Chen, W.-H., Yu, X., Liao, W.-C., Sohn, Y.S., Cecconello, A., Kozell, A., Nechushtai, R., Willner, I.: ATP-Responsive aptamer-based metal-organic framework nanoparticles (NMOFs) for the controlled release of loads and drugs. Adv. Funct. Mater. 27, 1702102 (2017)
Lazaro, I.A., Haddad, S., Sacca, S., Orellana-Tavra, C., Fairen-Jimenez, D., Forgan, R.S.: Selective surface PEGylation of UiO-66 nanoparticles for enhanced stability, cell uptake, and pH-responsive drug delivery. CHEM 2, 561–578 (2017)
Ito, M., Ishiwata, T., Anan, S., Kokado, K., Inoue, D., Kabir, A.M.R., Kakugo, A., Sada, K.: Construction and gliding of metal-organic frameworks and microtubule conjugates. ChemistrySelect 1, 5358–5362 (2016)
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Sada, K., Kokado, K. (2020). Click Chemistry to Metal-Organic Frameworks as a Synthetic Tool for MOF and Applications for Functional Materials. In: Sakamoto, M., Uekusa, H. (eds) Advances in Organic Crystal Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-15-5085-0_25
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