Molecular Fibers and Wires in Solid-State and Solution Self-Assemblies of Cyclodextrin [2]Rotaxanes

Maniam, Subashani; Cieslinski, Marta Maria; Lincoln, Stephen F.; Onagi, Hideki; Steel, Peter J.; Willis, Anthony C.; Easton, Christopher J.

doi:10.1021/ol8002145

Cited by 17 publications

(5 citation statements)

References 29 publications

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“…Even higher CIS values observed for PEI as compared to TETA (−2.3 versus −1.04 ppm) (despite the high binding constant for the latter) can reasonably be explained only by the formation of the pseudorotaxane type structures of PEI with SCA, when the linear part of polymer chains is deeply introduced into the calixarene cavity (Scheme d). Such systems are well-known for cyclodextrin-based systems . In the case of TETA, its short molecules probably slip through the cavity, which results in the lower CIS value.…”

Section: Resultsmentioning

confidence: 99%

NMR and Spectrophotometry Study of the Supramolecular Catalytic System Based on Polyethyleneimine and Amphiphilic Sulfonatomethylated Calix[4]Resorcinarene

et al. 2009

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The aggregation behavior and catalytic activity of the polyethyleneimine (PEI) and sulfonatomethylated calix[4]resorcinarene (SCA) based systems are studied by methods of the NMR and UV-vis spectroscopy. The investigation of the kinetics of hydrolysis of the p-nitrophenyl dimethyl phosphate revealed two reaction routes in both the single PEI solution and the binary PEI-SCA system. Although SCA alone shows no catalytic activity, a 10-fold synergetic catalytic effect is achieved in the binary PEI-SCA system as compared to the single PEI systems at the SCA concentrations below the critical micelle concentration (cmc) of 0.011 M originating from the tensiometry data. The inclusive type of interactions involving the calixarene cavity is shown to contribute to the PEI-SCA self-assembly in the concentration range below this cmc value, which is probably responsible for the above rate acceleration. The different modes of self-organization assuming the PEI inclusion into the calixarene cavity are discussed.

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Section: Resultsmentioning

confidence: 99%

NMR and Spectrophotometry Study of the Supramolecular Catalytic System Based on Polyethyleneimine and Amphiphilic Sulfonatomethylated Calix[4]Resorcinarene

et al. 2009

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“…Insulated molecular wires (IMWS), which are capable of connecting two entities attached to their chain ends 2 7 , are expected to be applicable to bridging the gap between molecular-based electronic devices and macroscopic electrodes or to wiring a single molecule into an electrical circuit 1 8 9 10 . To date, various methods of IMWS fabrication have been explored 7 11 12 13 14 15 . One promising method is the one-dimensional (1D) self-assembly of π-conjugated molecular building blocks 13 14 .…”

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confidence: 99%

Hierarchical Assembly of a Dual-responsive Macroscopic Insulated Molecular Wire Bundle in a Gradient System

Sheng

Chen

Yao

et al. 2015

Sci Rep

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Here, we report the hierarchical self-assembly of a cationic gemini amphiphile, Azo 1, in a composition gradient solution generated using solvent evaporation. As the gradient solution is formed, Azo 1 forms nanorods in the lower region of the solution. Depending on solvent composition, these nanorods can further develop into nanofibres, which can then intertwine to form double helices and other types of nanohelices in the upper region of the solution. Finally, a macroscopic wire bundle is formed via the fusion of nanohelices; this ribbon-like bundle exhibits elasticity and linear ohmic resistance properties. More intriguingly, this bundle exhibits photoresponsive properties that affect its deformation and conductivity, as well as a rapid electroresponse that affects its conductivity, indicating that it is feasible to control the charge pathway.

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“…In the solid state, one [2]pseudorotaxane (without stopper groups) of the -CD-bisimidazolyl complex (Baleizao et al, 2004) and several [3]pseudorotaxanes ofand -CDs have been reported (Wenz et al, 2006). Moreover, the [2]rotaxane type has been observed for -CD inclusion complexes with different stilbenes (Stanier et al, 2001;Cieslinski et al, 2006;Maniam et al, 2008), poly(p-phenylenevinylene) (Terao et al, 2004) and diphenylacetylene (Nishimura et al, 2008), and the [3]rotaxane-type for -CD with alkylene (Akae et al, 2016). Recently, spectroscopic evidence for [4]rotaxanes of permethyl--CD with alkylene (Akae et al, 2016) and -CD with alkynylpyrenes (Inouye et al, 2014) have been reported.…”

Section: (3)mentioning

confidence: 99%

Inclusion complex of β-cyclodextrin with coffee chlorogenic acid: new insights from a combined crystallographic and theoretical study

Aree

2019

Acta Crystallogr C Struct Chem

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This work reports the elusive structural evidence for the [4]pseudorotaxane of β-cyclodextrin (β-CD) with coffee chlorogenic acid (CGA), a conjugate of caffeic acid (CFA) and quinic acid (QNA). A single-crystal X-ray structure analysis of the inclusion complex β-cyclodextrin–chlorogenic acid–water (2/2/17), 2C42H70O35·2C16H18O9·17H2O, reveals that CGA threads through β-CD and assembles via O—H...O hydrogen bonds and parallel-displaced π–π interactions in the twofold symmetry-related dimer yielding a [4]pseudorotaxane, which is crystallographically observed for the first time in CD inclusion complexes. The encapsulation of the aromatic ring and C=C—C(=O)O chain in the β-CD dimeric cavity indicates that the CFA moiety plays a determinant role in complexation. This is in agreement with the DFT-derived relative thermodynamic stabilities of the trimodal β-CD–CGA inclusion complexes, that is, β-CD complexed with different CGA components: C=C—C(=O)O chain > cyclohexane ring > aromatic ring. The complexation stability is further enhanced in the dimeric β-CD–CGA complex, with the CFA moiety totally enclosed in the β-CD dimeric cavity.

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Molecular Fibers and Wires in Solid-State and Solution Self-Assemblies of Cyclodextrin [2]Rotaxanes

Cited by 17 publications

References 29 publications

NMR and Spectrophotometry Study of the Supramolecular Catalytic System Based on Polyethyleneimine and Amphiphilic Sulfonatomethylated Calix[4]Resorcinarene

NMR and Spectrophotometry Study of the Supramolecular Catalytic System Based on Polyethyleneimine and Amphiphilic Sulfonatomethylated Calix[4]Resorcinarene

Hierarchical Assembly of a Dual-responsive Macroscopic Insulated Molecular Wire Bundle in a Gradient System

Inclusion complex of β-cyclodextrin with coffee chlorogenic acid: new insights from a combined crystallographic and theoretical study

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