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- Publisher Website: 10.1021/jo401993n
- Scopus: eid_2-s2.0-84890163987
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Article: Synthesis of ExnBox cyclophanes
Title | Synthesis of Ex<sup>n</sup>Box cyclophanes |
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Authors | |
Issue Date | 2013 |
Citation | Journal of Organic Chemistry, 2013, v. 78, n. 23, p. 11962-11969 How to Cite? |
Abstract | A rapid and efficient synthesis of the extended bipyridinium-based class of cyclophanes - that is, ExnBox4+ (n = 0-3), where n is the number of p-phenylene rings inserted between the pyridinium rings - is demonstrated, resulting in much higher yields of products along with a reduced output of oligomeric byproducts. Although each cyclophane can be synthesized readily without the use of a precise stoichiometric amount of template, ExBox4+ can be prepared in 66% yield (following crystallization) using six equivalents of pyrene in a template-directed protocol. This new methodology has been employed to synthesize, in modest yield, a nearly 2.5 nm long cyclophane consisting of 12 aromatic rings. © 2013 American Chemical Society. |
Persistent Identifier | http://hdl.handle.net/10722/333057 |
ISSN | 2023 Impact Factor: 3.3 2023 SCImago Journal Rankings: 0.724 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Barnes, Jonathan C. | - |
dc.contributor.author | Juríček, Michal | - |
dc.contributor.author | Vermeulen, Nicolaas A. | - |
dc.contributor.author | Dale, Edward J. | - |
dc.contributor.author | Stoddart, J. Fraser | - |
dc.date.accessioned | 2023-10-06T05:16:25Z | - |
dc.date.available | 2023-10-06T05:16:25Z | - |
dc.date.issued | 2013 | - |
dc.identifier.citation | Journal of Organic Chemistry, 2013, v. 78, n. 23, p. 11962-11969 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/10722/333057 | - |
dc.description.abstract | A rapid and efficient synthesis of the extended bipyridinium-based class of cyclophanes - that is, ExnBox4+ (n = 0-3), where n is the number of p-phenylene rings inserted between the pyridinium rings - is demonstrated, resulting in much higher yields of products along with a reduced output of oligomeric byproducts. Although each cyclophane can be synthesized readily without the use of a precise stoichiometric amount of template, ExBox4+ can be prepared in 66% yield (following crystallization) using six equivalents of pyrene in a template-directed protocol. This new methodology has been employed to synthesize, in modest yield, a nearly 2.5 nm long cyclophane consisting of 12 aromatic rings. © 2013 American Chemical Society. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of Organic Chemistry | - |
dc.title | Synthesis of Ex<sup>n</sup>Box cyclophanes | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/jo401993n | - |
dc.identifier.scopus | eid_2-s2.0-84890163987 | - |
dc.identifier.volume | 78 | - |
dc.identifier.issue | 23 | - |
dc.identifier.spage | 11962 | - |
dc.identifier.epage | 11969 | - |
dc.identifier.eissn | 1520-6904 | - |
dc.identifier.isi | WOS:000328231600035 | - |