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Article: TetrazineBox: A Structurally Transformative Toolbox

TitleTetrazineBox: A Structurally Transformative Toolbox
Authors
Issue Date2020
Citation
Journal of the American Chemical Society, 2020, v. 142, n. 11, p. 5419-5428 How to Cite?
AbstractSynthetic macrocycles capable of undergoing allosteric regulation by responding to versatile external stimuli are the subject of increasing attention in supramolecular science. Herein, we report a structurally transformative tetracationic cyclophane containing two 3,6-bis(4-pyridyl)-l,2,4,5-tetrazine (4-bptz) units, which are linked together by two p-xylylene bridges. The cyclophane, which possesses modular redox states and structural post-modifications, can undergo two reversibly consecutive two-electron reductions, affording first its bisradical dicationic counterpart, and then subsequently the fully reduced species. Furthermore, one single-parent cyclophane can afford effectively three other new analogs through box-to-box cascade transformations, taking advantage of either reductions or an inverse electron-demand Diels-Alder (IEDDA) reaction. While all four new tetracationic cyclophanes adopt rigid and symmetric box-like conformations, their geometries in relation to size, shape, electronic properties, and binding affinities toward polycyclic aromatic hydrocarbons can be readily regulated. This structurally transformative tetracationic cyclophane performs a variety of new tasks as a result of structural post-modifications, thus serving as a toolbox for probing the radical properties and generating rapidly a range of structurally diverse cyclophanes by efficient divergent syntheses. This research lays a solid foundation for the introduction of the structurally transformative tetracationic cyclophane into the realm of mechanically interlocked molecules and will provide a toolbox to construct and operate intelligent molecular machines.
Persistent Identifierhttp://hdl.handle.net/10722/333425
ISSN
2023 Impact Factor: 14.4
2023 SCImago Journal Rankings: 5.489
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorGuo, Qing Hui-
dc.contributor.authorZhou, Jiawang-
dc.contributor.authorMao, Haochuan-
dc.contributor.authorQiu, Yunyan-
dc.contributor.authorNguyen, Minh T.-
dc.contributor.authorFeng, Yuanning-
dc.contributor.authorLiang, Jiaqi-
dc.contributor.authorShen, Dengke-
dc.contributor.authorLi, Penghao-
dc.contributor.authorLiu, Zhichang-
dc.contributor.authorWasielewski, Michael R.-
dc.contributor.authorFraser Stoddart, J.-
dc.date.accessioned2023-10-06T05:19:16Z-
dc.date.available2023-10-06T05:19:16Z-
dc.date.issued2020-
dc.identifier.citationJournal of the American Chemical Society, 2020, v. 142, n. 11, p. 5419-5428-
dc.identifier.issn0002-7863-
dc.identifier.urihttp://hdl.handle.net/10722/333425-
dc.description.abstractSynthetic macrocycles capable of undergoing allosteric regulation by responding to versatile external stimuli are the subject of increasing attention in supramolecular science. Herein, we report a structurally transformative tetracationic cyclophane containing two 3,6-bis(4-pyridyl)-l,2,4,5-tetrazine (4-bptz) units, which are linked together by two p-xylylene bridges. The cyclophane, which possesses modular redox states and structural post-modifications, can undergo two reversibly consecutive two-electron reductions, affording first its bisradical dicationic counterpart, and then subsequently the fully reduced species. Furthermore, one single-parent cyclophane can afford effectively three other new analogs through box-to-box cascade transformations, taking advantage of either reductions or an inverse electron-demand Diels-Alder (IEDDA) reaction. While all four new tetracationic cyclophanes adopt rigid and symmetric box-like conformations, their geometries in relation to size, shape, electronic properties, and binding affinities toward polycyclic aromatic hydrocarbons can be readily regulated. This structurally transformative tetracationic cyclophane performs a variety of new tasks as a result of structural post-modifications, thus serving as a toolbox for probing the radical properties and generating rapidly a range of structurally diverse cyclophanes by efficient divergent syntheses. This research lays a solid foundation for the introduction of the structurally transformative tetracationic cyclophane into the realm of mechanically interlocked molecules and will provide a toolbox to construct and operate intelligent molecular machines.-
dc.languageeng-
dc.relation.ispartofJournal of the American Chemical Society-
dc.titleTetrazineBox: A Structurally Transformative Toolbox-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/jacs.0c01114-
dc.identifier.pmid32083871-
dc.identifier.scopuseid_2-s2.0-85082094071-
dc.identifier.volume142-
dc.identifier.issue11-
dc.identifier.spage5419-
dc.identifier.epage5428-
dc.identifier.eissn1520-5126-
dc.identifier.isiWOS:000526392600054-

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