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, J. Fraser Stoddart

Research output: Contribution to journalArticle

8 Citations (Scopus)

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 languageEnglish
Pages (from-to)13835-13842
Number of pages8
JournalJournal of the American Chemical Society
Volume140
Issue number42
DOIs
Publication statusPublished - Oct 24 2018

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Fullerenes
Porphyrins
Viologens
Supramolecular chemistry
Fluorescence Spectrometry
X-Ray Diffraction
Fluorescence spectroscopy
Ultraviolet spectroscopy
Nuclear magnetic resonance
Single crystals
X ray diffraction
Research

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Shi, Y., Cai, K., Xiao, H., Liu, Z., Zhou, J., Shen, D., ... Fraser Stoddart, J. (2018). Selective Extraction of C70 by a Tetragonal Prismatic Porphyrin Cage. Journal of the American Chemical Society, 140(42), 13835-13842. https://doi.org/10.1021/jacs.8b08555

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 journalArticle

Shi, Y, Cai, K, Xiao, H, Liu, Z, Zhou, J, Shen, D, Qiu, Y, Guo, QH, Stern, C, Wasielewski, MR, Diederich, F, Goddard, WA & Fraser Stoddart, J 2018, 'Selective Extraction of C70 by a Tetragonal Prismatic Porphyrin Cage', Journal of the American Chemical Society, vol. 140, no. 42, pp. 13835-13842. https://doi.org/10.1021/jacs.8b08555
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. / Selective Extraction of C70 by a Tetragonal Prismatic Porphyrin Cage. In: Journal of the American Chemical Society. 2018 ; Vol. 140, No. 42. pp. 13835-13842.
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