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Issue 9, 2019
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2H NMR reveals liquid state-like dynamics of arene guests inside hexameric pyrogallol[4]arene capsules in the solid state

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Abstract

The dynamics of guests in molecular encapsulation complexes have been studied extensively in solution, but the corresponding behavior of those guests when the capsules are present in the solid state is not as well understood. Here we report on comparative solution 1H and solid-state 2H NMR measurements of encapsulation complexes of fluorene(-d2), fluoranthene(-d10), and pyrene(-d10) in pyrogallol[4]arene hexamers assembled in the solid state by ball milling. In solution, the 1H spectra show that these rigid guests tumble and exchange positions quickly within the capsules’ interiors, with the exception of pyrene, which has slower tumbling and positional exchange. Static solid-state 2H NMR using the deuterated guests shows that, when the capsules are in the solid state, their guests retain the liquid state-like dynamics observed for the capsules in solution. When the pyrogallol[4]arene hexamers’ pendant decyl groups were substituted with propyl groups, guest dynamics in the solid state were slowed. We propose that these pendant alkyl groups form an interdigitated and dynamic waxy domain surrounding the capsules in the solid state, and that the greater mobility of the decyl groups is translated across the walls of the host, resulting in more rapid guest dynamics in the capsules’ interiors.

Graphical abstract: 2H NMR reveals liquid state-like dynamics of arene guests inside hexameric pyrogallol[4]arene capsules in the solid state

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Publication details

The article was received on 11 Feb 2019, accepted on 29 Mar 2019 and first published on 01 Apr 2019


Article type: Research Article
DOI: 10.1039/C9QO00232D
Citation: Org. Chem. Front., 2019,6, 1361-1366

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    2H NMR reveals liquid state-like dynamics of arene guests inside hexameric pyrogallol[4]arene capsules in the solid state

    I. J. Islas, D. Stengel, C. A. Garcia, J. B. Addison, G. N. Samaan, G. P. Holland and B. W. Purse, Org. Chem. Front., 2019, 6, 1361
    DOI: 10.1039/C9QO00232D

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