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 |
|---|---|
| Pages (from-to) | 13835-13842 |
| Number of pages | 8 |
| Journal | Journal of the American Chemical Society |
| Volume | 140 |
| Issue number | 42 |
| DOIs | |
| Publication status | Published - Oct 24 2018 |
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ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry
Cite this
Selective Extraction of C70 by a Tetragonal Prismatic Porphyrin Cage. / Shi, Yi; Cai, Kang; Xiao, Hai; Liu, Zhichang; Zhou, Jiawang; Shen, Dengke; Qiu, Yunyan; Guo, Qing Hui; Stern, Charlotte; Wasielewski, Michael R; Diederich, François; Goddard, William A.; Fraser Stoddart, J.
In: Journal of the American Chemical Society, Vol. 140, No. 42, 24.10.2018, p. 13835-13842.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Selective Extraction of C70 by a Tetragonal Prismatic Porphyrin Cage
AU - Shi, Yi
AU - Cai, Kang
AU - Xiao, Hai
AU - Liu, Zhichang
AU - Zhou, Jiawang
AU - Shen, Dengke
AU - Qiu, Yunyan
AU - Guo, Qing Hui
AU - Stern, Charlotte
AU - Wasielewski, Michael R
AU - Diederich, François
AU - Goddard, William A.
AU - Fraser Stoddart, J.
PY - 2018/10/24
Y1 - 2018/10/24
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85055112066&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85055112066&partnerID=8YFLogxK
U2 - 10.1021/jacs.8b08555
DO - 10.1021/jacs.8b08555
M3 - Article
C2 - 30265801
AN - SCOPUS:85055112066
VL - 140
SP - 13835
EP - 13842
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 42
ER -