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Article: Assembly of supramolecular nanotubes from molecular triangles and 1,2-dihalohydrocarbons

TitleAssembly of supramolecular nanotubes from molecular triangles and 1,2-dihalohydrocarbons
Authors
Issue Date2014
Citation
Journal of the American Chemical Society, 2014, v. 136, n. 47, p. 16651-16660 How to Cite?
AbstractPrecise control of molecular assembly is a challenging goal facing supramolecular chemists. Herein, we report the highly specific assembly of a range of supramolecular nanotubes from the enantiomeric triangular naphthalenediimide-based macrocycles (RRRRRR)- and (SSSSSS)-NDI-Δ and a class of similar solvents, namely, the 1,2-dihalo-ethanes and -ethenes (DXEs). Three kinds of supramolecular nanotubes are formed from the columnar stacking of NDI-Δ units with a 60° mutual rotation angle as a result of cooperative [C-H···O] interactions, directing interactions of the [X···X]-bonded DXE chains inside the nanotubes and lateral [X···π] or [π···π] interactions. They include (i) semiflexible infinite nanotubes formed in the gel state from NDI-Δ and (E)-1,2-dichloroethene, (ii) rigid infinite nonhelical nanotubes produced in the solid state from NDI-Δ and BrCH2CH2Br, ClCH2CH2Br, and ClCH2CH2I, and (iii) a pair of rigid tetrameric, enantiomeric single-handed (P)- and (M)-helical nanotubes formed in the solid state from the corresponding (RRRRRR)- and (SSSSSS)-NDI-Δ with ClCH2CH2Cl. In case (i), only the electron-rich C=C double bond of (E)-1,2-dichloroethene facilitates the gelation of NDI-Δ. In cases (ii) and (iii), the lengths of anti-DXEs determine the translation of the chirality of NDI-Δ into the helicity of nanotubes. Only ClCH2CH2Cl induces single-handed helicity into the nanotubes. The subtle interplay of noncovalent bonding interactions, resulting from the tiny structural variations involving the DXE guests, is responsible for the diverse and highly specific assembly of NDI-Δ. This research highlights the critical role that guests play in constructing assembled superstructures of hosts and offers a novel approach to creating supramolecular nanotubes.
Persistent Identifierhttp://hdl.handle.net/10722/333096
ISSN
2023 Impact Factor: 14.4
2023 SCImago Journal Rankings: 5.489
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorLiu, Zhichang-
dc.contributor.authorLiu, Guoliang-
dc.contributor.authorWu, Yilei-
dc.contributor.authorCao, Dennis-
dc.contributor.authorSun, Junling-
dc.contributor.authorSchneebeli, Severin T.-
dc.contributor.authorNassar, Majed S.-
dc.contributor.authorMirkin, Chad A.-
dc.contributor.authorStoddart, J. Fraser-
dc.date.accessioned2023-10-06T05:16:42Z-
dc.date.available2023-10-06T05:16:42Z-
dc.date.issued2014-
dc.identifier.citationJournal of the American Chemical Society, 2014, v. 136, n. 47, p. 16651-16660-
dc.identifier.issn0002-7863-
dc.identifier.urihttp://hdl.handle.net/10722/333096-
dc.description.abstractPrecise control of molecular assembly is a challenging goal facing supramolecular chemists. Herein, we report the highly specific assembly of a range of supramolecular nanotubes from the enantiomeric triangular naphthalenediimide-based macrocycles (RRRRRR)- and (SSSSSS)-NDI-Δ and a class of similar solvents, namely, the 1,2-dihalo-ethanes and -ethenes (DXEs). Three kinds of supramolecular nanotubes are formed from the columnar stacking of NDI-Δ units with a 60° mutual rotation angle as a result of cooperative [C-H···O] interactions, directing interactions of the [X···X]-bonded DXE chains inside the nanotubes and lateral [X···π] or [π···π] interactions. They include (i) semiflexible infinite nanotubes formed in the gel state from NDI-Δ and (E)-1,2-dichloroethene, (ii) rigid infinite nonhelical nanotubes produced in the solid state from NDI-Δ and BrCH<inf>2</inf>CH<inf>2</inf>Br, ClCH<inf>2</inf>CH<inf>2</inf>Br, and ClCH<inf>2</inf>CH<inf>2</inf>I, and (iii) a pair of rigid tetrameric, enantiomeric single-handed (P)- and (M)-helical nanotubes formed in the solid state from the corresponding (RRRRRR)- and (SSSSSS)-NDI-Δ with ClCH<inf>2</inf>CH<inf>2</inf>Cl. In case (i), only the electron-rich C=C double bond of (E)-1,2-dichloroethene facilitates the gelation of NDI-Δ. In cases (ii) and (iii), the lengths of anti-DXEs determine the translation of the chirality of NDI-Δ into the helicity of nanotubes. Only ClCH<inf>2</inf>CH<inf>2</inf>Cl induces single-handed helicity into the nanotubes. The subtle interplay of noncovalent bonding interactions, resulting from the tiny structural variations involving the DXE guests, is responsible for the diverse and highly specific assembly of NDI-Δ. This research highlights the critical role that guests play in constructing assembled superstructures of hosts and offers a novel approach to creating supramolecular nanotubes.-
dc.languageeng-
dc.relation.ispartofJournal of the American Chemical Society-
dc.titleAssembly of supramolecular nanotubes from molecular triangles and 1,2-dihalohydrocarbons-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/ja509480u-
dc.identifier.pmid25357152-
dc.identifier.scopuseid_2-s2.0-84914128898-
dc.identifier.volume136-
dc.identifier.issue47-
dc.identifier.spage16651-
dc.identifier.epage16660-
dc.identifier.eissn1520-5126-
dc.identifier.isiWOS:000345720500028-

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