2007
DOI: 10.1002/anie.200700305
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A Liquid‐Crystalline Bistable [2]Rotaxane

Abstract: Entering a new phase: Mesogenic stoppers (purple) at the ends of the rod section of a switchable donor–acceptor [2]rotaxane induce the formation of a smectic A liquid‐crystalline (LC) phase over a wide temperature range. The bistable [2]rotaxane which contains a tetracationic cyclophane (blue), a tetrathiafulvalene unit (green), and a 1,5‐dioxynaphthalene unit (red) self‐assembles into a LC phase with a layer spacing of about 8 nm (see picture).

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Cited by 174 publications
(86 citation statements)
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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%
See 1 more Smart Citation
“…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%
“…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%
“…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%