Proline functionalization of the mesoporous metal-organic framework DUT-32

Kutzscher C, Hoffmann HC, Krause S, Stoeck U, Senkovska I, Brunner E, Kaskel S (2015)

Publication Type: Journal article

Publication year: 2015

Journal

Inorganic Chemistry American Chemical Society

Book Volume: 54

Pages Range: 1003-1009

Journal Issue: 3

DOI: 10.1021/ic502380q

Abstract

The linker functionalization strategy was applied to incorporate proline moieties into a metal-organic framework (MOF). When 4,4′-biphenyldicarboxylic acid was replaced with a Boc-protected proline-functionalized linker (H2L) in the synthesis of DUT-32 (DUT = Dresden University of Technology), a highly porous enantiomerically pure MOF (DUT-32-NHProBoc) was obtained, as could be confirmed by enantioselective high-performance liquid chromatography (HPLC) measurements and solid-state NMR experiments. Isotope labeling of the chiral side group proline enabled highly sensitive one- and two-dimensional solid-state 13C NMR experiments. For samples loaded with (S)-1-phenyl-2,2,2-trifluoroethanol [(S)-TFPE], the proline groups are shown to exhibit a lower mobility than that for (R)-TFPE-loaded samples. This indicates a preferred interaction of the shift agent (S)-TFPE with the chiral moieties. The high porosity of the compound is reflected by an exceptionally high ethyl cinnamate adsorption capacity. However, postsynthetic thermal deprotection of Boc-proline in the MOF leads to racemization of the chiral center, which was verified by stereoselective HPLC experiments and asymmetric catalysis of aldol addition.

Involved external institutions

Technische Universität Dresden DE Germany (DE)

How to cite

APA:

Kutzscher, C., Hoffmann, H.C., Krause, S., Stoeck, U., Senkovska, I., Brunner, E., & Kaskel, S. (2015). Proline functionalization of the mesoporous metal-organic framework DUT-32. Inorganic Chemistry, 54(3), 1003-1009. https://doi.org/10.1021/ic502380q

MLA:

Kutzscher, Christel, et al. "Proline functionalization of the mesoporous metal-organic framework DUT-32." Inorganic Chemistry 54.3 (2015): 1003-1009.

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