File Download

There are no files associated with this item.

  Links for fulltext
     (May Require Subscription)
Supplementary

Article: Supramolecular Gelation of Rigid Triangular Macrocycles through Rings of Multiple C-H⋯O Interactions Acting Cooperatively

TitleSupramolecular Gelation of Rigid Triangular Macrocycles through Rings of Multiple C-H⋯O Interactions Acting Cooperatively
Authors
Issue Date2016
Citation
Journal of Organic Chemistry, 2016, v. 81, n. 6, p. 2581-2588 How to Cite?
AbstractWhen equimolar solutions of the enantiomeric naphthalenediimide-based highly rigid triangles R-Δ and S-Δ in ClCH2CH2Cl are mixed, the racemate rac-Δ forms an organogel that is composed of interwoven fibers, resulting from the columnar stacking of the triangles in an alternating R-Δ/S-Δ fashion. Under identical conditions, the pure enantiomers do not form organogels. Density functional theory calculations reveal that the racemic RS dimer is more stable than the RR dimer as a result of the enantiomeric relationship between R-Δ and S-Δ, allowing them to act as two complementary rings comprised of 12 [C-H···O] interactions with an unprecedented and uninterrupted circular ADDAADDAADDA·DAADDAADDAAD alignment of hydrogen bond donors (D) and acceptors (A), in contrast with the square-wave manner in which the RR dimer forms a complementary yet interrupted ADADAD·DADADA circular sequence of six longer [C-H⋯O] hydrogen bonds. It follows that gelation is favored by weak interactions acting cooperatively in rings under precise stereoelectronic control.
Persistent Identifierhttp://hdl.handle.net/10722/333168
ISSN
2023 Impact Factor: 3.3
2023 SCImago Journal Rankings: 0.724
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorLiu, Zhichang-
dc.contributor.authorSun, Junling-
dc.contributor.authorZhou, Yu-
dc.contributor.authorZhang, Yu-
dc.contributor.authorWu, Yilei-
dc.contributor.authorNalluri, Siva Krishna Mohan-
dc.contributor.authorWang, Yuping-
dc.contributor.authorSamanta, Avik-
dc.contributor.authorMirkin, Chad A.-
dc.contributor.authorSchatz, George C.-
dc.contributor.authorStoddart, J. Fraser-
dc.date.accessioned2023-10-06T05:17:14Z-
dc.date.available2023-10-06T05:17:14Z-
dc.date.issued2016-
dc.identifier.citationJournal of Organic Chemistry, 2016, v. 81, n. 6, p. 2581-2588-
dc.identifier.issn0022-3263-
dc.identifier.urihttp://hdl.handle.net/10722/333168-
dc.description.abstractWhen equimolar solutions of the enantiomeric naphthalenediimide-based highly rigid triangles R-Δ and S-Δ in ClCH2CH2Cl are mixed, the racemate rac-Δ forms an organogel that is composed of interwoven fibers, resulting from the columnar stacking of the triangles in an alternating R-Δ/S-Δ fashion. Under identical conditions, the pure enantiomers do not form organogels. Density functional theory calculations reveal that the racemic RS dimer is more stable than the RR dimer as a result of the enantiomeric relationship between R-Δ and S-Δ, allowing them to act as two complementary rings comprised of 12 [C-H···O] interactions with an unprecedented and uninterrupted circular ADDAADDAADDA·DAADDAADDAAD alignment of hydrogen bond donors (D) and acceptors (A), in contrast with the square-wave manner in which the RR dimer forms a complementary yet interrupted ADADAD·DADADA circular sequence of six longer [C-H⋯O] hydrogen bonds. It follows that gelation is favored by weak interactions acting cooperatively in rings under precise stereoelectronic control.-
dc.languageeng-
dc.relation.ispartofJournal of Organic Chemistry-
dc.titleSupramolecular Gelation of Rigid Triangular Macrocycles through Rings of Multiple C-H⋯O Interactions Acting Cooperatively-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/acs.joc.6b00281-
dc.identifier.scopuseid_2-s2.0-84961832076-
dc.identifier.volume81-
dc.identifier.issue6-
dc.identifier.spage2581-
dc.identifier.epage2588-
dc.identifier.eissn1520-6904-
dc.identifier.isiWOS:000372664700036-

Export via OAI-PMH Interface in XML Formats


OR


Export to Other Non-XML Formats