Mechanically interlocked daisy-chain-like structures as multidimensional molecular muscles

Chang, Jia-Cheng; Tseng, Shin-Han; Lai, Chien‐Chen; Liu, Yi-Hung; Peng, Shie‐Ming; Chiu, Sheng‐Hsien

doi:10.1038/nchem.2608

Cited by 86 publications

(46 citation statements)

References 45 publications

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“…In principle highero rder daisy chains could also be utilized. [57] These results are significant because they showt hat materials capable of macroscopica ctuation can be constructed by rely-ing on molecular machines.S uch soft materials are of high interest for technological applications,e .g.,i nr obotics and prosthetics.…”

Section: Materials Science and Engineering:t Owards Artificial Musclementioning

confidence: 99%

Making and Operating Molecular Machines: A Multidisciplinary Challenge

et al. 2018

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Movement is one of the central attributes of life, and a key feature in many technological processes. While artificial motion is typically provided by macroscopic engines powered by internal combustion or electrical energy, movement in living organisms is produced by machines and motors of molecular size that typically exploit the energy of chemical fuels at ambient temperature to generate forces and ultimately execute functions. The progress in several areas of chemistry, together with an improved understanding of biomolecular machines, has led to the development of a large variety of wholly synthetic molecular machines. These systems have the potential to bring about radical innovations in several areas of technology and medicine. In this Minireview, we discuss, with the help of a few examples, the multidisciplinary aspects of research on artificial molecular machines and highlight its translational character.

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Section: Materials Science and Engineering:t Owards Artificial Musclementioning

confidence: 99%

Making and Operating Molecular Machines: A Multidisciplinary Challenge

et al. 2018

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“…In particular, owing to the sphere-like dendritic nature of T3B-RD, they could translate each [2]rotaxane with individual 1D molecular shuttling into a three-dimensional (3D) molecular size control within its multiple switchable rotaxane motif. This macromolecule could also induce an overall extension–contraction 2 , 8 , 25 or breathing molecular motion 26 – 29 via the polyrotaxane molecular shuttling of T3B-RD simultaneously. The size, polarity, and the accessibility of the void spaces in the T3B-RD can be controlled.…”

Section: Introductionmentioning

confidence: 99%

Higher-generation type III-B rotaxane dendrimers with controlling particle size in three-dimensional molecular switching

et al. 2018

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Type III-B rotaxane dendrimers (T3B-RDs) are hyperbranched macromolecules with mechanical bonds on every branching unit. Here we demonstrate the design, synthesis, and characterization of first to third (G1–G3), and up to the fourth (G4) generation (MW > 22,000 Da) of pure organic T3B-RDs and dendrons through the copper-catalyzed alkyne–azide cycloaddition (CuAAC) reaction. By utilizing multiple molecular shuttling of the mechanical bonds within the sphere-like macromolecule, a collective three-dimensional contract-extend molecular motion is demonstrated by diffusion ordered spectroscopy (DOSY) and atomic force microscopy (AFM). The discrete T3B-RDs are further observed and characterized by AFM, dynamic light scattering (DLS), and mass spectrometry (MS). The binding of chlorambucil and pH-triggered switching of the T3B-RDs are also characterized by 1H-NMR spectroscopy.

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“…Precursor 1 represents one of the few examples in which interlocked daisy chains comprising ar igid extended pconjugated rod were synthesized. [14] To the best of our knowledge, this is the only example in which this couldb ea ccomplished in an aqueouse nvironment. As malla mount of organic additive was still required to achieve as ignificant solubility, which is ac onsequence of the large organic structure combined with the zwitterionic character of the molecule.…”

Section: Resultsmentioning

confidence: 83%

“…Covalently bound host-guest conjugates result in the formation of supramolecular daisy chains, [9][10][11][12][13][14][15][16] if the molecular structures are designed appropriately to rule out unimolecular selfcomplexation and formation of non-interlinked, intermolecular aggregates. [16] Due to the hermaphroditic nature of daisy chains, only one component is required for supramolecular complex formation,w hich is appealing for the construction of molecular devices because it is possible to obtain aggregates of different sizes by rational design,a sd emonstrated by the synthesis of linear and cyclic molecular muscles, [12][13][14][17][18][19] polymers [11,[20][21][22] and gels. [13,23,24] Most daisy chains are based on recognition features that have only limited applicability in water, either due to limited solubility or functional disruption of the recognition site.…”

Section: Introductionmentioning

confidence: 99%

Aqueous Assembly of Zwitterionic Daisy Chains

Aeschi

Drayss‐Orth

Valášek

et al. 2018

Chemistry A European J

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The synthesis and characterization of zwitterionic molecular [c2]- and [a2]-daisy chains are described, relying on recognition of a positively charged cyclophane and a negatively charged oligo(phenylene-ethynylene) (OPE) rod in aqueous medium. For this purpose, syntheses of an acetylene-functionalized macrocyclic receptor and a water-soluble OPE-rod as the guest component are presented, from which a heteroditopic daisy chain monomer was prepared. This monomer aggregated strongly in water/methanol 4:1 and formed molecular daisy chains, which were isolated as interlocked species from a stoppering reaction at 1 mm concentration. The cyclic dimer [c2] was the main product with an isolated yield of 30 % and consisted of a mixture of diastereomers, as evidenced by H NMR spectroscopy.

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Mechanically interlocked daisy-chain-like structures as multidimensional molecular muscles

Cited by 86 publications

References 45 publications

Making and Operating Molecular Machines: A Multidisciplinary Challenge

Making and Operating Molecular Machines: A Multidisciplinary Challenge

Higher-generation type III-B rotaxane dendrimers with controlling particle size in three-dimensional molecular switching

Aqueous Assembly of Zwitterionic Daisy Chains

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