2007
DOI: 10.1002/anie.200604664
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Direct Translation of Chiral Recognition into Mechanical Motion

Abstract: Chiral recognition is of fundamental importance in nature, and also for a manifold of chemical applications. Enantioselectivity is the landmark of many new synthetic strategies and the basis of separation techniques, for example, for drugs. In all these processes the recognition manifests itself in the predominant formation of one enantiomer, be it after the synthesis or after the separation. The direct translation of chiral recognition into mechanical motions has to the best of our knowledge never been report… Show more

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Cited by 28 publications
(30 citation statements)
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References 20 publications
(8 reference statements)
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“…Only with His was there a moderate enantioselectivity in the presence of acetic acid as cofactor (Table S3). As already described in our preliminary communication, [31] the most dramatic enantioselectivity is reached with tartaric acid derivatives in which phenyl moieties provide for significant cation-π interactions with the protonated nitrogen centres of chitosan. The corresponding mode of interaction was corroborated by MAS-NMR spectra, with quite selective ring-current effects of the effector phenyl groups on the aminoglucose protons of the polymer.…”
Section: Difference With Enantiomeric Effectorsmentioning
confidence: 75%
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“…Only with His was there a moderate enantioselectivity in the presence of acetic acid as cofactor (Table S3). As already described in our preliminary communication, [31] the most dramatic enantioselectivity is reached with tartaric acid derivatives in which phenyl moieties provide for significant cation-π interactions with the protonated nitrogen centres of chitosan. The corresponding mode of interaction was corroborated by MAS-NMR spectra, with quite selective ring-current effects of the effector phenyl groups on the aminoglucose protons of the polymer.…”
Section: Difference With Enantiomeric Effectorsmentioning
confidence: 75%
“…[30] This compartmentalization effect allows a ten-fold sensitivity increase of the chitosan gel. [31] For example, the same contraction occurs at a 1 m DBTA effector concentration at a particle volume of about 7 mm 3 as at 0.1 m with a gel piece of about 0.2 mm 3 ( Table S4). The chemomechanical response velocity can also be increased significantly if, with smaller gel particles, the surface to volume ratio (S/V) is increased.…”
Section: Response Velocity and Sensitivity Increase By Reducing The Smentioning
confidence: 87%
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“…[1][2][3][4] Polymers are also excellent platforms for molecular recognition of guest molecules as they often respond differently to closely related species, such as structural isomers and even enantiomers. 5,6 In most cases the molecular recognition process taking place between the polymer and its guest molecules involves diffusion of the guest molecule inside the polymer and formation of specific interactions between binding sites of the polymer and complimentary binding sites of the guest molecules. This normally involves some degree of structural reorganization followed by changes in macroscopic properties of the medium, such as the volume and the Young's modulus.…”
mentioning
confidence: 99%
“…[ 4 , 5 ] For different chiral molecular species, many synthetic chiral recognition systems have been developed, [6][7][8] with applications such as chiral detection and separation, and asymmetric catalysis, etc. However, recognition is usually only the fi rst step, and a more appealing task is to translate the chiral signals into other processes or macroscopic properties and functions of materials, [ 9 ] which will bring great advantages to applications, but is quite challenging for chemists. Here we report the chirality-triggered wettability switching on smart copolymer fi lms containing dipeptide units.…”
mentioning
confidence: 99%