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Selective Extraction of C_(70) by a Tetragonal Prismatic Porphyrin Cage

Shi, Yi and Cai, Kang and Xiao, Hai and Liu, Zhichang and Zhou, Jiawang and Shen, Dengke and Qiu, Yunyan and Guo, Qing-Hui and Stern, Charlotte and Wasielewski, Michael R. and Diederich, François and Goddard, William A., III and Stoddart, J. Fraser (2018) Selective Extraction of C_(70) by a Tetragonal Prismatic Porphyrin Cage. Journal of the American Chemical Society, 140 (42). pp. 13835-13842. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20181001-131357964

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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 C_(60) and C_(70) 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 C_(70) than for C_(60), resulting in a selective extraction of C_(70) from a C_(60)-enriched fullerene mixture (C_(60)/C_(70) = 10/1), demonstrating the potential of the cage as an attractive receptor for fullerene separation.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/jacs.8b08555DOIArticle
https://pubs.acs.org/doi/suppl/10.1021/jacs.8b08555PublisherSupporting Information
ORCID:
AuthorORCID
Shi, Yi0000-0002-1981-8350
Cai, Kang0000-0002-8883-0142
Xiao, Hai0000-0001-9399-1584
Liu, Zhichang0000-0003-3412-512X
Zhou, Jiawang0000-0002-2399-0030
Qiu, Yunyan0000-0001-9279-4714
Wasielewski, Michael R.0000-0003-2920-5440
Goddard, William A., III0000-0003-0097-5716
Stoddart, J. Fraser0000-0003-3161-3697
Alternate Title:Selective Extraction of C70 by a Tetragonal Prismatic Porphyrin Cage
Additional Information:© 2018 American Chemical Society. Received: August 9, 2018; Published: September 28, 2018. 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.). Author Contributions: Y.S. and K.C. contributed equally. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
King Abdul-Aziz City for Science and Technology (KACST)UNSPECIFIED
Northwestern UniversityUNSPECIFIED
NSFEFRI-1332411
Department of Energy (DOE)DE-FG02-99ER14999
Other Numbering System:
Other Numbering System NameOther Numbering System ID
WAG1303
Record Number:CaltechAUTHORS:20181001-131357964
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20181001-131357964
Official Citation:Selective Extraction of C70 by a Tetragonal Prismatic Porphyrin Cage. Yi Shi, Kang Cai, Hai Xiao, Zhichang Liu, Jiawang Zhou, Dengke Shen, Yunyan Qiu, Qing-Hui Guo, Charlotte Stern, Michael R. Wasielewski, François Diederich, William A. Goddard, III, and J. Fraser Stoddart. Journal of the American Chemical Society 2018 140 (42), 13835-13842. DOI: 10.1021/jacs.8b08555
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:90072
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:01 Oct 2018 20:40
Last Modified:22 Mar 2019 23:14

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