Supramolecular Assembly of Tris(4-carboxyphenyl)arenes: Relationship between Molecular Structure and Solid-State Catenation Motifs

Title:
Supramolecular Assembly of Tris(4-carboxyphenyl)arenes: Relationship between Molecular Structure and Solid-State Catenation Motifs
Authors:
Lai, Holden W. H.; Wiscons, Ren A.; Zentner, Cassandra A.; Zeller, Matthias; Rowsell, Jesse L. C.
Abstract:
The crystal structures of seven 1,3,5-tris(4-carboxyphenyl)arenes with functionalized central arene rings are reported. The formation of (6,3) hcb hexagonal sheets as a result of carboxylic acid dimer formation was observed in most of the crystal structures, with the exception of two compounds with functional groups capable of forming hydrogen bonds, namely, 2,4,6-tris(4-carboxyphenyl)-1,3-diaminobenzene and 2,4,6-tris(4-carboxyphenyl)-3-methylaniline. These structures were found to incorporate THF solvent molecules in their hydrogen-bonding motif, giving rise to distorted pseudohexagonal arrays. Functional groups on the central ring were found to influence stacking distances, stacking offsets, inclination angles, degree of catenation, and dimensions of solvent-occupied channels. To better understand and appreciate these complicated crystal structures, they were categorized into four distinct stacking/catenation families: simple stacking, single-layer offset catenation, double-layer offset catenation, and rotated-layer catenation. The unique structure of the unfunctionalized parent compound 1,3,5-tris(4-carboxyphenyl)benzene is rationalized in light of the structural behavior of its derivatives.
Citation:
Holden, W.H. Lai, Ren A. Wiscons, Cassandra A. Zentner, Matthias Zeller, and Jesse L.C. Rowsell. 2016. "Supramolecular Assembly of Tris(4-carboxyphenyl)arenes: Relationship between Molecular Structure and Solid-State Catenation Motifs." Crystal Growth & Design 16(2): 821-833.
Publisher:
American Chemical Society
DATE ISSUED:
2016-02-03
Department:
Chemistry and Biochemistry
Type:
Article
PUBLISHED VERSION:
10.1021/acs.cgd.5b01416
Additional Links:
http://pubs.acs.org/doi/abs/10.1021/acs.cgd.5b01416
PERMANENT LINK:
http://hdl.handle.net/11282/597029

Full metadata record

DC FieldValue Language
dc.contributor.authorLai, Holden W. H.en
dc.contributor.authorWiscons, Ren A.en
dc.contributor.authorZentner, Cassandra A.en
dc.contributor.authorZeller, Matthiasen
dc.contributor.authorRowsell, Jesse L. C.en
dc.date.accessioned2016-02-23T14:58:42Zen
dc.date.available2016-02-23T14:58:42Zen
dc.date.issued2016-02-03en
dc.identifier.citationHolden, W.H. Lai, Ren A. Wiscons, Cassandra A. Zentner, Matthias Zeller, and Jesse L.C. Rowsell. 2016. "Supramolecular Assembly of Tris(4-carboxyphenyl)arenes: Relationship between Molecular Structure and Solid-State Catenation Motifs." Crystal Growth & Design 16(2): 821-833.en
dc.identifier.issn1528-7483en
dc.identifier.urihttp://hdl.handle.net/11282/597029en
dc.description.abstractThe crystal structures of seven 1,3,5-tris(4-carboxyphenyl)arenes with functionalized central arene rings are reported. The formation of (6,3) hcb hexagonal sheets as a result of carboxylic acid dimer formation was observed in most of the crystal structures, with the exception of two compounds with functional groups capable of forming hydrogen bonds, namely, 2,4,6-tris(4-carboxyphenyl)-1,3-diaminobenzene and 2,4,6-tris(4-carboxyphenyl)-3-methylaniline. These structures were found to incorporate THF solvent molecules in their hydrogen-bonding motif, giving rise to distorted pseudohexagonal arrays. Functional groups on the central ring were found to influence stacking distances, stacking offsets, inclination angles, degree of catenation, and dimensions of solvent-occupied channels. To better understand and appreciate these complicated crystal structures, they were categorized into four distinct stacking/catenation families: simple stacking, single-layer offset catenation, double-layer offset catenation, and rotated-layer catenation. The unique structure of the unfunctionalized parent compound 1,3,5-tris(4-carboxyphenyl)benzene is rationalized in light of the structural behavior of its derivatives.en
dc.language.isoen_USen
dc.publisherAmerican Chemical Societyen
dc.identifier.doi10.1021/acs.cgd.5b01416en
dc.relation.urlhttp://pubs.acs.org/doi/abs/10.1021/acs.cgd.5b01416en
dc.subject.departmentChemistry and Biochemistryen_US
dc.titleSupramolecular Assembly of Tris(4-carboxyphenyl)arenes: Relationship between Molecular Structure and Solid-State Catenation Motifsen_US
dc.typeArticleen
dc.identifier.journalCrystal Growth & Designen
dc.identifier.volume16en_US
dc.identifier.issue2en_US
dc.identifier.startpage821en_US
dc.rightsArchived with thanks to Crystal Growth & Designen
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