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dc.contributor.authorJia, Fei
dc.contributor.authorSchröder, Hendrik V.
dc.contributor.authorYang, Liu-Pan
dc.contributor.authorvon Essen, Carolina
dc.contributor.authorSobottka, Sebastian
dc.contributor.authorSarkar, Biprajit
dc.contributor.authorRissanen, Kari
dc.contributor.authorJiang, Wei
dc.contributor.authorSchalley, Christoph A.
dc.date.accessioned2020-02-19T13:40:45Z
dc.date.available2020-02-19T13:40:45Z
dc.date.issued2020
dc.identifier.citationJia, 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. <i>Journal of the American Chemical Society</i>, <i>142</i>(7), 3306-3310. <a href="https://doi.org/10.1021/jacs.9b11685" target="_blank">https://doi.org/10.1021/jacs.9b11685</a>
dc.identifier.otherCONVID_34596810
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/67900
dc.description.abstract“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.en
dc.format.mimetypeapplication/pdf
dc.languageeng
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.relation.ispartofseriesJournal of the American Chemical Society
dc.rightsIn Copyright
dc.subject.otherredox-reaktio
dc.subject.otherhapetus-pelkistysreaktio
dc.subject.otherredox reactions
dc.subject.otherhydrocarbons
dc.subject.otheraromatic compunds
dc.subject.otheroxidation cations
dc.titleRedox-Responsive Host-Guest Chemistry of a Flexible Cage with Naphthalene Walls
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-202002192128
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineOrgaaninen kemiafi
dc.contributor.oppiaineOrganic Chemistryen
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.type.coarhttp://purl.org/coar/resource_type/c_2df8fbb1
dc.description.reviewstatuspeerReviewed
dc.format.pagerange3306-3310
dc.relation.issn0002-7863
dc.relation.numberinseries7
dc.relation.volume142
dc.type.versionacceptedVersion
dc.rights.copyright© 2020 American Chemical Society
dc.rights.accesslevelopenAccessfi
dc.subject.ysoaromaattiset yhdisteet
dc.subject.ysokationit
dc.subject.ysohapetus
dc.subject.ysohiilivedyt
dc.subject.ysohapetus-pelkistysreaktio
dc.subject.ysopelkistys
dc.format.contentfulltext
jyx.subject.urihttp://www.yso.fi/onto/yso/p23502
jyx.subject.urihttp://www.yso.fi/onto/yso/p27230
jyx.subject.urihttp://www.yso.fi/onto/yso/p9135
jyx.subject.urihttp://www.yso.fi/onto/yso/p1169
jyx.subject.urihttp://www.yso.fi/onto/yso/p28877
jyx.subject.urihttp://www.yso.fi/onto/yso/p9117
dc.rights.urlhttp://rightsstatements.org/page/InC/1.0/?language=en
dc.relation.datasethttps://pubs.acs.org/doi/suppl/10.1021/jacs.9b11685/suppl_file/ja9b11685_si_001.pdf
dc.relation.doi10.1021/jacs.9b11685
jyx.fundinginformationThis research was supported by the National Natural Science Foundation of China (grant nos. 21572097, 21822104, and 21801125), the Shenzhen Special Funds (KQJSCX20170728162528382, JCYJ20180504165810828), and the Shenzhen Nobel Prize Scientists Laboratory Project (C17213101). F.J. thanks the China Scholarship Council (CSC) for a Ph.D. fellowship. We thank Henrik Hupatz for helpful discussions and help with UV/vis experiments, Dr. Carlo Fasting for help with the purity analysis of the naphthocage, and Dr. Andreas Schäfer for help with EXSY measurements. Funding from the Deutsche Forschungsgemeinschaft (CRC 765 and core facility BioSupraMol) is gratefully acknowledged.
dc.type.okmA1


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