A1 Journal article (refereed)
Redox-Responsive Host-Guest Chemistry of a Flexible Cage with Naphthalene Walls (2020)

Jia, F., Schröder, H. V., Yang, L.-P., von Essen, C., Sobottka, S., Sarkar, B., Rissanen, K., Jiang, W., & Schalley, C. A. (2020). Redox-Responsive Host-Guest Chemistry of a Flexible Cage with Naphthalene Walls. Journal of the American Chemical Society, 142(7), 3306-3310. https://doi.org/10.1021/jacs.9b11685

JYU authors or editors

Publication details

All authors or editors: Jia, Fei; Schröder, Hendrik V.; Yang, Liu-Pan; von Essen, Carolina; Sobottka, Sebastian; Sarkar, Biprajit; Rissanen, Kari; Jiang, Wei; Schalley, Christoph A.

Journal or series: Journal of the American Chemical Society

ISSN: 0002-7863

eISSN: 1520-5126

Publication year: 2020

Volume: 142

Issue number: 7

Pages range: 3306-3310

Publisher: American Chemical Society

Publication country: United States

Publication language: English

DOI: https://doi.org/10.1021/jacs.9b11685

Research data link: https://pubs.acs.org/doi/suppl/10.1021/jacs.9b11685/suppl_file/ja9b11685_si_001.pdf

Publication open access: Not open

Publication channel open access:

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/67900

Additional information: The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.9b11685;
Experimental and theoretical details, 1H NMR and UV/vis spectra of the complexes, cyclic voltammetry experiments, and single-crystal X-ray data, including Figures S1–S53 and Tables S1 and S2 (PDF); https://pubs.acs.org/doi/suppl/10.1021/jacs.9b11685/suppl_file/ja9b11685_si_001.pdf;
Crystallographic data for MV2+@NC (CIF); https://pubs.acs.org/doi/suppl/10.1021/jacs.9b11685/suppl_file/ja9b11685_si_002.cif


“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.

Keywords: hydrocarbons; aromatic compounds; oxidation-reduction reaction; oxidation (active); reduction (chemistry); cations

Free keywords: redox reactions; hydrocarbons; aromatic compunds; oxidation cations

Contributing organizations

Ministry reporting: Yes

Reporting Year: 2020

JUFO rating: 3

Last updated on 2021-07-07 at 21:32