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Redox-Responsive Host–Guest Chemistry of a Flexible Cage with Naphthalene Walls

Fei Jia, Hendrik V. Schröder, Liu‐Pan Yang, Carolina von Eßen, Sebastian Sobottka, Biprajit Sarkar, Kari Rissanen, Wei Jiang, Christoph A. Schalley

2020Journal of the American Chemical Society57 citationsDOIOpen Access PDF

Abstract

) to aromatic (di)cationic guests, i.e., the tetrathiafulvalene mono- and dication and methyl viologen. Intercalation of the guests between two naphthalene walls is mediated by C-H···O, C-H···π, and cation···π interactions. The guests can be switched into and out of the cage by redox processes with high binding selectivity. Oxidation of the flexible cage itself in the absence of a guest leads to a stable radical cation with the oxidized naphthalene intercalated between and stabilized by the other two. Encapsulated guest cations are released from the cavity upon cage oxidation, paving the way to future applications in redox-controlled guest release or novel stimuli-responsive materials.

Topics & Concepts

ChemistryCageNaphthaleneRedoxHost (biology)Host–guest chemistryNanotechnologyOrganic chemistrySupramolecular chemistryMoleculeEcologyMaterials scienceMathematicsBiologyCombinatoricsSupramolecular Chemistry and ComplexesMolecular Sensors and Ion DetectionNeuroscience and Neuropharmacology Research
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