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Synthesis, Configurational Analysis, Molecular Recognition and Chirality Sensing of Methylene‐Bridged Naphthotubes

Von Wiley-VCH zur Verfügung gestellt

Methylene-bridged naphthotubes have been successfully developed. The three-membered naphthotubes possess a rigid and well-defined cavity, while four-membered naphthotubes possess a double-cavity conformation or a self-filling conformation depending on the alkoxy length. They show quite strong binding affinities (up to 108 M−1) to organic cations and can be used as chirality sensors for chiral organic cations.


Abstract

Macrocyclic hosts with a well-defined cavity are particularly appealing for supramolecular chemistry, but they are still rare. In this research, we reported a new class of macrocyclic hosts, namely methylene-bridged naphthotubes, with well-defined cavities. They were synthesized through TFA-catalyzed Friedel–Crafts reactions between alkoxy-substituted bisnaphthalenes and paraformaldehyde. A configurational selection was observed. Three-membered macrocycles possess a single cavity, while four-membered macrocycles adopt a double-cavity conformation or a self-filling conformation depending on the alkoxy length. The small homologue shows quite strong binding affinities (up to 108 M−1) to organic cations, which is better than structurally similar but flexible macrocycles. This demonstrates the advantage of a well-defined cavity in molecular recognition. Moreover, these naphthotubes can be used as chirality sensors for chiral organic cations through different chirality transfer mechanisms.

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