Unusual Solid-State Behavior in a Neutral [2]Catenane Bearing a Hydrolyzable Component

Fallon, Gary D.; Lee, Marcia A.-P.; Langford, Steven J.; Nichols, Peter J.

doi:10.1021/ol036116s

Cited by 32 publications

(15 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The shift of Δ δ 0.2–0.4 is consistent with other examples of interactions between two aromatic species such as those observed by Fallon et al. between a [2]catenane species bearing interacting NDI and 1/5HQ units . An interesting and different trend is seen for 8 though, bearing the C 6 H 4 group.…”

Section: Resultsmentioning

confidence: 99%

Systematically Studying the Effect of Fluoride on the Properties of Cyclophanes Bearing Naphthalene Diimide and Dialkoxyaryl Groups

Young

Drew

Maniam

et al. 2017

Chemistry An Asian Journal

Self Cite

View full text Add to dashboard Cite

Anion-p interactions between the Lewis basic anion fluoride and p-acidic naphthalene diimidewas systematically studied in as eries of cyclophanes in which the properties are modulated through the influenceo fas econd, electron-rich aromatic unit. Thes ystems and subsequently generated radical anions, upon addition of fluoride,w ere studied by absorption spectroscopic and EPR techniques. The results infer am odulation as ar esult of the nature and strength of the p-p interaction in the macrocyclic structure.

show abstract

Section: Resultsmentioning

confidence: 99%

Systematically Studying the Effect of Fluoride on the Properties of Cyclophanes Bearing Naphthalene Diimide and Dialkoxyaryl Groups

Young

Drew

Maniam

et al. 2017

Chemistry An Asian Journal

Self Cite

View full text Add to dashboard Cite

show abstract

“…One of the best‐explored motifs is the purple charge‐transfer (CT) complex formed by dialkoxynaphthalene (DAN) donors and naphthalenediimide (NDI) acceptors. These complexes have already been of use to create single‐ and double‐stranded oligo‐DAN–NDI foldamers,23–25 switchable DAN–NDI rotaxanes26, 27 and DAN–NDI catenanes 28–30…”

Section: Introductionmentioning

confidence: 99%

Ligand‐Gated Synthetic Ion Channels

Talukdar

Bollot

Mareda

et al. 2005

Chemistry A European J

115

View full text Add to dashboard Cite

Supramolecular pi-stack architecture is fundamental in DNA chemistry but absent in biological and synthetic ion channels and pores. Here, a novel rigid-rod pi-stack architecture is introduced to create synthetic ion channels with characteristics that are at the forefront of rational design, that is, ligand gating by a conformational change of the functional supramolecule. Namely, the intercalation of electron-rich aromatics is designed to untwist inactive electron-poor helical pi-stacks without internal space into open barrel-stave ion channels. Conductance experiments in planar lipid bilayers corroborate results from spherical bilayers and molecular modeling: Highly cooperative and highly selective ligand gating produces small, long-lived, weakly anion selective, ohmic ion channels. Structural studies conducted under conditions relevant for function provide experimental support for helix-barrel transition as origin of ligand gating. Control experiments demonstrate that minor structural changes leading to internal decrowding suffice to cleanly annihilate chiral self-organization and function.

show abstract

“…Owing to the electron deficiencyo ft he p-conjugated NDI units,d iscrete arraysa nd Borromean rings wereo btained following at wo-step self-assembly of the binuclear clips and carefullys elected linkers. From previousw ork, we have learnedt hat, owingt ot heir electron deficiency,t he NDI derivativescould also be employed as p acceptors to preparer otaxanesa nd catenanest hrough various strategies, for example, template synthesis [11] and dynamic covalentc hemistry. [12] Based on these previous studies, we hypothesized that crown ethers could take parti nt he Cp*M-directedself-assembly process to obtain suprastructures with sophisticated topologies.Here, we report the unprecedented Cp*Rh-a nd Cp*Ir-directed self-assembly of pseudorotaxanes driven by donor-acceptor interactions between electron-deficient NDI units andt he electron-rich crown ether 1,5-dinaphtho[38]crown-10.…”

mentioning

confidence: 99%

Donor–Acceptor [2]‐ and [3]Catenanes Assembled from Versatile Pre‐Organized Cp*Rh/Ir‐Directed Pseudorotaxane Tectons

Liu

Lin

et al. 2019

Chemistry A European J

View full text Add to dashboard Cite

A stepwise self‐assembly protocol has been used to synthesize [2]‐ and [3]catenanes. Firstly, binuclear Cp*Rh/Ir‐directed (Cp*=pentamethylcyclopentadienyl) pseudorotaxanes were prepared through self‐assembly, driven by donor–acceptor interactions between electron‐deficient naphthalenediimide (NDI) units and an electron‐rich crown ether. Subsequently, the pre‐organized pseudorotaxanes were applied as tectons for self‐assembly of [2]‐ and [3]catenanes by combination with very simple linkers. The structures of the catenanes were confirmed by NMR spectroscopy, ESI mass spectrometry, single‐crystal X‐ray diffraction analysis, and elemental analysis.

show abstract

Unusual Solid-State Behavior in a Neutral [2]Catenane Bearing a Hydrolyzable Component

Cited by 32 publications

References 17 publications

Systematically Studying the Effect of Fluoride on the Properties of Cyclophanes Bearing Naphthalene Diimide and Dialkoxyaryl Groups

Systematically Studying the Effect of Fluoride on the Properties of Cyclophanes Bearing Naphthalene Diimide and Dialkoxyaryl Groups

Ligand‐Gated Synthetic Ion Channels

Donor–Acceptor [2]‐ and [3]Catenanes Assembled from Versatile Pre‐Organized Cp*Rh/Ir‐Directed Pseudorotaxane Tectons

Contact Info

Product

Resources

About