6533b83afe1ef96bd12a7b78
RESEARCH PRODUCT
Redox-Responsive Host–Guest Chemistry of a Flexible Cage with Naphthalene Walls
Christoph A. SchalleyHendrik V. SchröderBiprajit SarkarLiu-pan YangKari RissanenWei JiangFei JiaFei JiaSebastian SobottkaCarolina Von Essensubject
Intercalation (chemistry)Cationic polymerizationmacromolecular substancesGeneral Chemistry010402 general chemistry01 natural sciencesBiochemistryRedoxCatalysis0104 chemical sciencesDicationchemistry.chemical_compoundColloid and Surface ChemistrychemistryRadical ionPolymer chemistryHost–guest chemistryTetrathiafulvaleneNaphthalenedescription
"Naphthocage", a naphthalene-based organic cage, reveals very strong binding (up to 1010 M-1) 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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2020-02-04 | Journal of the American Chemical Society |