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Article: Two-point halogen bonding between 3,6-dihalopyromellitic diimides
Title | Two-point halogen bonding between 3,6-dihalopyromellitic diimides |
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Authors | |
Issue Date | 2014 |
Citation | Chemical Science, 2014, v. 5, n. 11, p. 4242-4248 How to Cite? |
Abstract | The syntheses of 3,6-dichloro-, -dibromo-, and -diiodopyromellitic diimides - ACl, ABr, and AI, respectively - have been achieved. X-Ray crystallography of single crystals of ACl and ABr unveils the formation of extensive halogen-bonding networks in the solid state as a consequence of interactions between the lone pairs on the carbonyl oxygen atoms with the σ-holes of the halogen atoms. Further, the solid-state superstructure of diiodopyromellitic diimide is characterised by the formation of associated halogen-π dimers. The co-crystallisation of ACl or ABr with a 1,5-diaminonaphthalene derivative DN yields co-crystals of a mixed-stack charge-transfer (CT) complex which are supported by an expansive hydrogen-bonded network in addition to halogen-bonded belts that bring adjacent mixed-stacks into association with each other. 2,6-Dimethoxynaphthalene (DO) proved to be an effective CT complement to AI, yielding solvent-free co-crystals with superstructures which are comprised of a 1 - 2 ratio of AI to DO. This dimeric halogen-bonding motif is reminiscent of the formation of hydrogen-bonded dimers between carboxylic acids. |
Persistent Identifier | http://hdl.handle.net/10722/333627 |
ISSN | 2021 Impact Factor: 9.969 2020 SCImago Journal Rankings: 3.687 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Cao, Dennis | - |
dc.contributor.author | Hong, Michael | - |
dc.contributor.author | Blackburn, Anthea K. | - |
dc.contributor.author | Liu, Zhichang | - |
dc.contributor.author | Holcroft, James M. | - |
dc.contributor.author | Stoddart, J. Fraser | - |
dc.date.accessioned | 2023-10-06T05:21:08Z | - |
dc.date.available | 2023-10-06T05:21:08Z | - |
dc.date.issued | 2014 | - |
dc.identifier.citation | Chemical Science, 2014, v. 5, n. 11, p. 4242-4248 | - |
dc.identifier.issn | 2041-6520 | - |
dc.identifier.uri | http://hdl.handle.net/10722/333627 | - |
dc.description.abstract | The syntheses of 3,6-dichloro-, -dibromo-, and -diiodopyromellitic diimides - ACl, ABr, and AI, respectively - have been achieved. X-Ray crystallography of single crystals of ACl and ABr unveils the formation of extensive halogen-bonding networks in the solid state as a consequence of interactions between the lone pairs on the carbonyl oxygen atoms with the σ-holes of the halogen atoms. Further, the solid-state superstructure of diiodopyromellitic diimide is characterised by the formation of associated halogen-π dimers. The co-crystallisation of ACl or ABr with a 1,5-diaminonaphthalene derivative DN yields co-crystals of a mixed-stack charge-transfer (CT) complex which are supported by an expansive hydrogen-bonded network in addition to halogen-bonded belts that bring adjacent mixed-stacks into association with each other. 2,6-Dimethoxynaphthalene (DO) proved to be an effective CT complement to AI, yielding solvent-free co-crystals with superstructures which are comprised of a 1 - 2 ratio of AI to DO. This dimeric halogen-bonding motif is reminiscent of the formation of hydrogen-bonded dimers between carboxylic acids. | - |
dc.language | eng | - |
dc.relation.ispartof | Chemical Science | - |
dc.title | Two-point halogen bonding between 3,6-dihalopyromellitic diimides | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1039/c4sc00999a | - |
dc.identifier.scopus | eid_2-s2.0-84907551421 | - |
dc.identifier.volume | 5 | - |
dc.identifier.issue | 11 | - |
dc.identifier.spage | 4242 | - |
dc.identifier.epage | 4248 | - |
dc.identifier.eissn | 2041-6539 | - |
dc.identifier.isi | WOS:000343004300017 | - |