Redox-Responsive Host–Guest Chemistry of a Flexible Cage with Naphthalene Walls
“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··...
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| Veröffentlicht in: | Journal of the American Chemical Society 2020-02, Vol.142 (7), p.3306-3310 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 142 |
| creator | Jia, Fei Schröder, Hendrik V Yang, Liu-Pan von Essen, Carolina Sobottka, Sebastian Sarkar, Biprajit Rissanen, Kari Jiang, Wei Schalley, Christoph A |
| description | “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. |
| doi_str_mv | 10.1021/jacs.9b11685 |
| format | Article |
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| title | Redox-Responsive Host–Guest Chemistry of a Flexible Cage with Naphthalene Walls |
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