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- Publisher Website: 10.1021/jacs.8b03407
- Scopus: eid_2-s2.0-85046633290
- PMID: 29723466
- WOS: WOS:000434101100007
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Article: Toward a Charged Homo[2]catenane Employing Diazaperopyrenium Homophilic Recognition
Title | Toward a Charged Homo[2]catenane Employing Diazaperopyrenium Homophilic Recognition |
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Authors | |
Issue Date | 2018 |
Citation | Journal of the American Chemical Society, 2018, v. 140, n. 21, p. 6540-6544 How to Cite? |
Abstract | An octacationic diazaperopyrenium (DAPP2+)-based homo[2]catenane (DAPPHC8+), wherein no fewer than eight positive charges are associated within a mechanically interlocked molecule, has been produced in 30% yield under ambient conditions as a result of favorable homophilic interactions, reflecting a delicate balance between strong π- π interactions and the destabilizing penalty arising from Coulombic repulsions between DAPP2+ units. This DAPPHC8+ catenane is composed of two identical mechanically interlocked tetracationic cyclophanes, namely DAPPBox4+, each of which contains one DAPP2+ unit and one extended viologen (ExBIPY2+) unit, linked together by two p-xylylene bridges. The solid-state structure of the homo[2]catenane demonstrates how homophilic interactions play an important role in the formation of DAPPHC8+, in which the mean ring planes of the two DAPPBox4+ cyclophanes are oriented at about 60° with respect to each other, with a centroid-to-centroid separation of 3.7 Å between the mean planes of the outer ExBIPY2+ and inner DAPP2+ units, and 3.6 Å between the mean planes of the two inner DAPP2+ units. We show that irradiation of the DAPPHC8+ catenane at 330 nm in acetonitrile solution results in simultaneous energy and electron transfer. The latter occurs from the inner DAPP2+ dimer to the outer ExBIPY2+ unit, leading to the generation of a temporary charge-separated state within a rigid and robust homo[2]catenane. Compared to DAPPBox4+, both forward- and back-electron transfer in DAPPHC8+ occur with faster rates, owing to the closer proximity between the electron donor and acceptor in the homo[2]catenane than in the separated cyclophane. |
Persistent Identifier | http://hdl.handle.net/10722/333326 |
ISSN | 2023 Impact Factor: 14.4 2023 SCImago Journal Rankings: 5.489 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Gong, Xirui | - |
dc.contributor.author | Zhou, Jiawang | - |
dc.contributor.author | Hartlieb, Karel J. | - |
dc.contributor.author | Miller, Claire | - |
dc.contributor.author | Li, Peng | - |
dc.contributor.author | Farha, Omar K. | - |
dc.contributor.author | Hupp, Joseph T. | - |
dc.contributor.author | Young, Ryan M. | - |
dc.contributor.author | Wasielewski, Michael R. | - |
dc.contributor.author | Stoddart, J. Fraser | - |
dc.date.accessioned | 2023-10-06T05:18:30Z | - |
dc.date.available | 2023-10-06T05:18:30Z | - |
dc.date.issued | 2018 | - |
dc.identifier.citation | Journal of the American Chemical Society, 2018, v. 140, n. 21, p. 6540-6544 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10722/333326 | - |
dc.description.abstract | An octacationic diazaperopyrenium (DAPP2+)-based homo[2]catenane (DAPPHC8+), wherein no fewer than eight positive charges are associated within a mechanically interlocked molecule, has been produced in 30% yield under ambient conditions as a result of favorable homophilic interactions, reflecting a delicate balance between strong π- π interactions and the destabilizing penalty arising from Coulombic repulsions between DAPP2+ units. This DAPPHC8+ catenane is composed of two identical mechanically interlocked tetracationic cyclophanes, namely DAPPBox4+, each of which contains one DAPP2+ unit and one extended viologen (ExBIPY2+) unit, linked together by two p-xylylene bridges. The solid-state structure of the homo[2]catenane demonstrates how homophilic interactions play an important role in the formation of DAPPHC8+, in which the mean ring planes of the two DAPPBox4+ cyclophanes are oriented at about 60° with respect to each other, with a centroid-to-centroid separation of 3.7 Å between the mean planes of the outer ExBIPY2+ and inner DAPP2+ units, and 3.6 Å between the mean planes of the two inner DAPP2+ units. We show that irradiation of the DAPPHC8+ catenane at 330 nm in acetonitrile solution results in simultaneous energy and electron transfer. The latter occurs from the inner DAPP2+ dimer to the outer ExBIPY2+ unit, leading to the generation of a temporary charge-separated state within a rigid and robust homo[2]catenane. Compared to DAPPBox4+, both forward- and back-electron transfer in DAPPHC8+ occur with faster rates, owing to the closer proximity between the electron donor and acceptor in the homo[2]catenane than in the separated cyclophane. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of the American Chemical Society | - |
dc.title | Toward a Charged Homo[2]catenane Employing Diazaperopyrenium Homophilic Recognition | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/jacs.8b03407 | - |
dc.identifier.pmid | 29723466 | - |
dc.identifier.scopus | eid_2-s2.0-85046633290 | - |
dc.identifier.volume | 140 | - |
dc.identifier.issue | 21 | - |
dc.identifier.spage | 6540 | - |
dc.identifier.epage | 6544 | - |
dc.identifier.eissn | 1520-5126 | - |
dc.identifier.isi | WOS:000434101100007 | - |