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.
N1 - Funding Information:
This research is part of the Joint Center of Excellence in Integrated Nano-Systems (JCIN) at King Abdulaziz City of Science and Technology (KACST) and Northwestern University (NU). The authors thank both KACST and NU for their continued support of this research. Computational investigations were supported by the U.S. National Science Foundation under grant no. EFRI-1332411 (W.A.G. and H.X.). This work was also supported by the U.S. Department of Energy, Office of Science Office of Basic Energy Sciences under Award DE-FG02-99ER14999 (M.R.W. and J.Z.).
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.
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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 -