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Rigid, biconical hydrogen-bonded dimers that strongly encapsulate cationic guests in solution and the solid state.

ABSTRACT: The octol of a new rigid, tetraarylene-bridged cavitand was investigated for self-assembly behaviour in solution. ¹H and DOSY NMR spectroscopic experiments show that the cavitand readily dimerizes through an unusual seam of interdigitated hydrogen-bonds that is resistant to disruption by polar co-solvents. The well-defined cavity encapsulates small cationic guests, but not their neutral counterparts, restricting the conformation of sequestered tetraethylammonium in solution and the solid state.

SUBMITTER: Smith JN

PROVIDER: S-EPMC8442710 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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Rigid, biconical hydrogen-bonded dimers that strongly encapsulate cationic guests in solution and the solid state.

Smith Jordan N JN Ennis Courtney C Lucas Nigel T NT

Chemical science 20210811 35

The octol of a new rigid, tetraarylene-bridged cavitand was investigated for self-assembly behaviour in solution. <sup>1</sup>H and DOSY NMR spectroscopic experiments show that the cavitand readily dimerizes through an unusual seam of interdigitated hydrogen-bonds that is resistant to disruption by polar co-solvents. The well-defined cavity encapsulates small cationic guests, but not their neutral counterparts, restricting the conformation of sequestered tetraethylammonium in solution and the so ...[more]

PMID: 34659726

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