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NMR-crystallographic study of two-dimensionally self-assembled cyclohexane-based low-molecular-mass organic compounds

DOI zum Zitieren der Version auf EPub Bayreuth: https://doi.org/10.15495/EPub_UBT_00004747
URN to cite this document: urn:nbn:de:bvb:703-epub-4747-0

Title data

Schmidt, Marko ; Zehe, Christoph S. ; Siegel, Renee ; Heigl, Johannes U. ; Steinlein, Christoph ; Schmidt, Hans-Werner ; Senker, Jürgen:
NMR-crystallographic study of two-dimensionally self-assembled cyclohexane-based low-molecular-mass organic compounds.
In: ChrystEngComm. Vol. 15 (2013) Issue 43 . - pp. 8784-8796.
ISSN 1466-8033
DOI der Verlagsversion: https://doi.org/10.1039/c3ce41158c

Project information

Project title:
Project's official titleProject's id
Von partikulären Nanosystemen zur MesotechnologieSFB 840

Project financing: Deutsche Forschungsgemeinschaft

Abstract

Using a combined approach based on scanning electron microscopy, powder X-ray diffraction as well as 1D and 2D multinuclear solid-state NMR spectroscopy, we were able to determine the morphology and the crystal structures for a set of three supramolecular compounds with different hydrogen bonding motifs, namely N,N′-(cyclohexane-trans-1,4-diyl)bis(2,2-dimethylpropanamide) 1, 1,1′-(cyclohexane-trans-1,4-diyl)bis(3-tert-butylurea) 2 and N1,N4-bis(tert-butylcarbamoyl)cyclohexane-trans-1,4-dicarboxamide 3. Based on a complete signal assignment of the 1D solid-state MAS NMR spectra (1H, 13C, 15N) employing 2D HETCOR experiments and a quantitative evaluation of the corresponding resonances, the content of the asymmetric unit was determined to one half of a molecule. Probing the molecular configuration with 1H–1H double-quantum experiments revealed an intramolecular hydrogen bond for compound 3 while 1 and 2 form exclusively intermolecular H-bonds. Ab initio structure solutions applying real space methods with an included close-contact penalty were carried out for all compounds. The following Rietveld refinements led to excellent wRp-values between 2.5% and 4.1%. Compounds 1 and 2 crystallise isostructurally in the monoclinic space group P21/c exhibiting a pseudo-biaxial hydrogen bond motif. 3 crystallises in the triclinic space group Pwith intermolecular head-to-tail hydrogen bonds connecting the molecules to one-dimensional ribbons. Nevertheless, all compounds grow in a sheet-like morphology with lateral dimensions of several hundred micrometres indicating a fast growth in two dimensions along two of the crystal axes. Since all three molecules possess inversion symmetry cancelling the molecular dipole moment the growth mechanism itself has to be dominantly driven by the formation of hydrogen bond networks.

Further data

Item Type: Article in a journal
Additional notes (visible to public): ISI:000325815200018
DDC Subjects: 500 Science > 540 Chemistry
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Inorganic Chemistry III > Chair Inorganic Chemistry III - Univ.-Prof. Dr. Jürgen Senker
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Macromolecular Chemistry I > Chair Macromolecular Chemistry I - Univ.-Prof. Dr. Hans-Werner Schmidt
Research Institutions > Research Centres > Bayreuth Institute of Macromolecular Research - BIMF
Research Institutions > Research Centres > Bayreuth Center for Colloids and Interfaces - BZKG
Research Institutions > Collaborative Research Centers, Research Unit > SFB 840 Von partikulären Nanosystemen zur Mesotechnologie
Research Institutions > Collaborative Research Centers, Research Unit > SFB 840 Von partikulären Nanosystemen zur Mesotechnologie > SFB 840 - TP B 4
Faculties
Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Inorganic Chemistry III
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Macromolecular Chemistry I
Research Institutions
Research Institutions > Research Centres
Research Institutions > Collaborative Research Centers, Research Unit
Language: English
Originates at UBT: Yes
URN: urn:nbn:de:bvb:703-epub-4747-0
Date Deposited: 02 Sep 2020 07:11
Last Modified: 16 Sep 2020 08:11
URI: https://epub.uni-bayreuth.de/id/eprint/4747

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