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. 2019 Dec 4;141(48):18949-18953.
doi: 10.1021/jacs.9b10741. Epub 2019 Nov 18.

Selective Separation of Polyaromatic Hydrocarbons by Phase Transfer of Coordination Cages

Dawei Zhang  1 , Tanya K Ronson  1 , Roy Lavendomme  1 , Jonathan R Nitschke  1
Affiliations

Selective Separation of Polyaromatic Hydrocarbons by Phase Transfer of Coordination Cages

Dawei Zhang et al. J Am Chem Soc. .

Abstract

Here we report a new supramolecular strategy for the selective separation of specific polycyclic aromatic hydrocarbons (PAHs) from mixtures. The use of a triethylene glycol-functionalized formylpyridine subcomponent allowed the construction of an FeII4L4 tetrahedron 1 that was capable of transferring between water and nitromethane layers, driven by anion metathesis. Cage 1 selectively encapsulated coronene from among a mixture of eight different types of PAHs in nitromethane, bringing it into a new nitromethane phase by transiting through an intermediate water phase. The bound coronene was released from 1 upon addition of benzene, and both the cage and the purified coronene could be separated via further phase separation.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Subcomponent Self-Assembly of Cage 1
Figure 1
Figure 1
PAH guests for 1.
Figure 2
Figure 2
Partial 1H NMR spectra (CD3NO2, 500 MHz, 25 °C) of 1 (0.13 mM) after the addition of increasing amounts of coronene and then following further addition of deuterated benzene (100 μL to a 500 μL sample) to the mixture.
Figure 3
Figure 3
Sequential phase transfer of 1 (0.13 mM) by addition of sulfate and triflimide anions, from CD3NO2 (lower layers) to D2O (upper layers) and back again.
Figure 4
Figure 4
Selective separation and recovery of coronene from a mixture of other PAHs including anthracene, phenanthrene, pyrene, chrysene, triphenylene, perylene, and corannulene. All upper layers in these schematic vials are D2O, and the lower layers are CD3NO2. (a) Cage 1 took up coronene selectively in CD3NO2 (0.090 mM 1; 0.33 mM coronene, and 0.090 mM of each of the other PAHs) and (b) transferred to the aqueous layer together with its coronene cargo after the addition of SO42–; (c) replacement of the CD3NO2 layer and addition of Tf2N– drove the complex into CD3NO2. (d) Cage 1 discharged the coronene cargo upon addition of C6D6, and the released coronene (e) was separated by transferring empty 1 to D2O upon addition of SO42–. (f) Cage 1 was recovered in fresh CD3NO2 following the addition of Tf2N–. Free 1 paired with SO42– in D2O could also directly extract coronene from a new mixture of PAHs in CD3NO2 (e→b).
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