Abstract
Along with the advent of supramolecular chemistry, research on fullerene receptors based on noncovalent bonding interactions has attracted a lot of attention. Here, we present the design and synthesis of a cationic molecular cage: a cyclophane composed of two tetraphenylporphyrins, bridged face-to-face by four viologen units in a rhomboid prismatic manner. The large cavity inside the cage, as well as the favorable donor-acceptor interactions between the porphyrin panels and the fullerene guests, enables the cage to be an excellent fullerene receptor. The 1:1 host-guest complexes formed between the cage and both C60 and C70 were characterized in solution by HRMS and NMR, UV-vis and fluorescence spectroscopies, and confirmed in the solid state by single-crystal X-ray diffraction analyses. The results from solution studies reveal that the cage has a much stronger binding for C70 than for C60, resulting in a selective extraction of C70 from a C60-enriched fullerene mixture (C60/C70 = 10/1), demonstrating the potential of the cage as an attractive receptor for fullerene separation.
Original language | English (US) |
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Pages (from-to) | 13835-13842 |
Number of pages | 8 |
Journal | Journal of the American Chemical Society |
Volume | 140 |
Issue number | 42 |
DOIs | |
State | Published - Oct 24 2018 |
ASJC Scopus subject areas
- Catalysis
- General Chemistry
- Biochemistry
- Colloid and Surface Chemistry
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Dive into the research topics of 'Selective Extraction of C70 by a Tetragonal Prismatic Porphyrin Cage'. Together they form a unique fingerprint.Datasets
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CCDC 1840375: Experimental Crystal Structure Determination
Shi, Y. (Contributor), Cai, K. (Contributor), Xiao, H. (Contributor), Liu, Z. (Contributor), Zhou, J. (Contributor), Shen, D. (Contributor), Qiu, Y. (Contributor), Guo, Q.-H. (Contributor), Stern, C. (Contributor), Wasielewski, M. R. (Contributor), Diederich, F. (Contributor), Goddard, W. A. (Contributor) & Fraser, S. J. (Contributor), Cambridge Crystallographic Data Centre, 2018
DOI: 10.5517/ccdc.csd.cc1zs1yr, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1zs1yr&sid=DataCite
Dataset
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CCDC 1840376: Experimental Crystal Structure Determination
Shi, Y. (Contributor), Cai, K. (Contributor), Xiao, H. (Contributor), Liu, Z. (Contributor), Zhou, J. (Contributor), Shen, D. (Contributor), Qiu, Y. (Contributor), Guo, Q.-H. (Contributor), Stern, C. (Contributor), Wasielewski, M. R. (Contributor), Diederich, F. (Contributor), Goddard, W. A. (Contributor) & Fraser, S. J. (Contributor), Cambridge Crystallographic Data Centre, 2018
DOI: 10.5517/ccdc.csd.cc1zs1zs, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1zs1zs&sid=DataCite
Dataset
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CCDC 1840374: Experimental Crystal Structure Determination
Shi, Y. (Creator), Cai, K. (Creator), Xiao, H. (Creator), Liu, Z. (Creator), Zhou, J. (Creator), Shen, D. (Creator), Qiu, Y. (Creator), Guo, Q.-H. (Creator), Stern, C. (Creator), Wasielewski, M. R. (Creator), Diederich, F. (Creator), Goddard, W. A. (Contributor) & Fraser, S. J. (Contributor), Cambridge Crystallographic Data Centre, 2018
DOI: 10.5517/ccdc.csd.cc1zs1xq, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1zs1xq&sid=DataCite
Dataset