A Liquid‐Crystalline Bistable [2]Rotaxane

Aprahamian, Ivan; Yasuda, Takuma; Ikeda, Taichi; Saha, Sourav; Dichtel, William R.; Isoda, Kyosuke; Kato, Takashi; Stoddart, J. Fraser

doi:10.1002/anie.200700305

Cited by 172 publications

(84 citation statements)

References 87 publications

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“…Furthermore, carefully designed compounds can incorporate recognition stations that can be turned "on" or "off" by a variety of means, permitting direct control over molecular-scale movements within MIMs. These unique molecular machines based on MIMs working in concert have been incorporated into drug-delivery vehicles, [60][61][62][63][64][65][66] electrochromic systems, 19,[67][68][69][70] and molecular electronic devices. 26,55,[71][72][73][74][75][76][77][78] Switchable rotaxanes are particularly well-suited for use as artificial muscles because of the potential to harness the collective efforts of ensembles of linear molecules to exert linear forces, as opposed to catenanes, which exhibit radial motions.…”

Section: Rotaxane-based Redox-driven Molecular Machinesmentioning

confidence: 99%

“…The pH-switchable [c2]daisy chain molecules are readily amenable to modification with carefully chosen functional groups. This modification would enable future work toward incorporating these types of pHswitchable muscle molecules into cantilever devices and the production of functionalized muscle molecules that could be incorporated into liquid crystalline 68 or polymeric 100 systems. The material properties of these networked MIMs would then be responsive to changes in pH at the monomeric level.…”

Section: Rotaxane-based Redox-driven Molecular Machinesmentioning

confidence: 99%

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Molecular, Supramolecular, and Macromolecular Motors and Artificial Muscles

Li¹,

Paxton²,

Baughman³

et al. 2009

MRS Bull.

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Recent developments in chemical synthesis, nanoscale assembly, and molecularscale measurements enable the extension of the concept of macroscopic machines to the molecular and supramolecular levels. Molecular machines are capable of performing mechanical movements in response to external stimuli. They offer the potential to couple electrical or other forms of energy to mechanical action at the nano-and molecular scales. Working hierarchically and in concert, they can form actuators referred to as artificial muscles, in analogy to biological systems. We describe the principles behind driven motion and assembly at the molecular scale and recent advances in the field of molecular-level electromechanical machines, molecular motors, and artificial muscles. We discuss the challenges and successes in making these assemblies work cooperatively to function at larger scales.

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Section: Rotaxane-based Redox-driven Molecular Machinesmentioning

confidence: 99%

Section: Rotaxane-based Redox-driven Molecular Machinesmentioning

confidence: 99%

Molecular, Supramolecular, and Macromolecular Motors and Artificial Muscles

Li¹,

Paxton²,

Baughman³

et al. 2009

MRS Bull.

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“…However, it seems reasonable that, before artificial molecular machines can find applications in many fields of technology, they have to be interfaced with the macroscopic world by ordering them in some way so that they can behave coherently and can be addressed in space [96]. New generations of molecular machines and motors organized at interfaces [97], deposited on surfaces [98][99][100][101][102], embedded into liquid crystals [103][104][105] and polymers [106], or immobilized into membranes [107] or porous materials [23,108], have started to appear. On the basis of recent experiments [109,110] showing that the collective operation of machine-molecules in carefully engineered surface-deposited monolayers can indeed develop mechanical work at a larger scale, one can optimistically hope that useful devices based on artificial nanomachines will see the light in a not too distant future.…”

Section: Resultsmentioning

confidence: 99%

Molecular machines operated by light

Venturi

2008

Open Chemistry

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Abstract:The bottom-up construction and operation of machines and motors of molecular size is a topic of great interest in nanoscience, and a fascinating challenge of nanotechnology. Researchers in this field are stimulated and inspired by the outstanding progress of molecular biology that has begun to reveal the secrets of the natural nanomachines which constitute the material base of life. Like their macroscopic counterparts, nanoscale machines need energy to operate. Most molecular motors of the biological world are fueled by chemical reactions, but research in the last fifteen years has demonstrated that light energy can be used to power nanomachines by exploiting photochemical processes in appropriately designed artificial systems. As a matter of fact, light excitation exhibits several advantages with regard to the operation of the machine, and can also be used to monitor its state through spectroscopic methods. In this review we will illustrate the design principles at the basis of photochemically driven molecular machines, and we will describe a few examples based on rotaxane-type structures investigated in our laboratories. © Versita Warsaw and Springer-Verlag Berlin

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“…We have used the CuAAC reaction extensively to prepare both one-station [13,14] and switchable two-station [15,16] donor/acceptor rotaxanes based on the cyclobis-(paraquat-p-phenylene) (CBPQT 4 þ ) [30 -32] as the p-acceptor ring (Scheme 1). Donor/acceptor rotaxanes based on CBPQT 4 þ as the tetracationic cyclophane p-acceptor ring component have traditionally been prepared [33] by synthetic procedures that (i) create the p-donating dumbbell-shaped template, and then (ii) clip the components of the CBPQT 4 þ ring around the template, to afford a rotaxane (clipping, Figure 2D).…”

Section: Preparation Of Rotaxanes By a Click Chemistry Approachmentioning

confidence: 99%

Rotaxanes and Catenanes by Click Chemistry

et al. 2007

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Copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition between terminal alkynes and azides -also known as the copper (Cu)-catalyzed Azide-Alkyne Cycloaddition (CuAAC) -has been used in the syntheses of molecular compounds with diverse structures and functions, owing to its functional group tolerance, facile execution, and mild reaction conditions under which it can be promoted. Recently, rotaxanes of four different structural types, as well as donor/acceptor catenanes, have been prepared using CuAAC, attesting to its tolerance to supramolecular interactions as well. In one instance of a rotaxane synthesis, the catalytic role of copper has been combined successfully with its previously documented ability to preorganize rotaxane precursors, i.e., form pseudorotaxanes. The crystal structure of a donor/acceptor catenane formed using the CuAAC reaction indicates that any secondary [p ··· p] interactions between the 1,2,3-triazole ring and the bipyridinium p-acceptor are certainly not destabilizing. Finally, the preparation of robust rotaxane and catenane molecular monolayers onto metal and semiconductor surfaces is premeditated based upon recent advances in the use of the Huisgen reaction for surface functionalization.

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A Liquid‐Crystalline Bistable [2]Rotaxane

Cited by 172 publications

References 87 publications

Molecular, Supramolecular, and Macromolecular Motors and Artificial Muscles

Molecular, Supramolecular, and Macromolecular Motors and Artificial Muscles

Molecular machines operated by light

Rotaxanes and Catenanes by Click Chemistry

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