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Artificial Molecular Machines.

Erbas-Cakmak S, Leigh DA, McTernan CT, Nussbaumer AL - Chem. Rev. (2015)

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Affiliation: School of Chemistry, University of Manchester , Oxford Road, Manchester M13 9PL, United Kingdom.

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bonded molecules and on catenanes and rotaxanes in which switching of other protic solvents... This effect (listed in descending binding ability) stations on the thread, macrocycle In these systems, fast-responding reporters are preferred... practical applications by utilizing molecular scale changes to create macroscopic effects... The thread of these rotaxanes included an anthracene fluorophore similar application in synthetic polymers often furnishes a useful result... of Brownian motion can be exploited to great effect in the synthesis every aspect of functional molecule and materials design... An improved robotics” in which ratcheted motions of molecular components

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(a)Chiraloptical switching upon photoinduced shuttling of themacrocycle between fumaramide (green) and peptide (orange) stations;the chiral center of the peptide station is highlighted by a blackcircle. (b) Percentage of E isomer calculated using 1H NMR (left y axis) and induced CD absorptionat 246 nm after alternating irradiation between 254 nm (half integer)and 312 nm (integers) (right y axis). Reprinted withpermission from ref (1326). Copyright 2003 American Chemical Society.
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fig47: (a)Chiraloptical switching upon photoinduced shuttling of themacrocycle between fumaramide (green) and peptide (orange) stations;the chiral center of the peptide station is highlighted by a blackcircle. (b) Percentage of E isomer calculated using 1H NMR (left y axis) and induced CD absorptionat 246 nm after alternating irradiation between 254 nm (half integer)and 312 nm (integers) (right y axis). Reprinted withpermission from ref (1326). Copyright 2003 American Chemical Society.

Mentions: The responsive nature of induced circular dichroism makesit aninteresting phenomenon to study with the CD response of one specieschanging upon its interaction with another.387,1315−1319 The transformation of an achiral carbon center to a chiral one uponhydrogen-bonding-dependent symmetry breaking provided an early exampleof the influence of supramolecular interactions on chirality.1320 A number of chiral supramolecular assemblies,1315,1316,1321 chiral spaces (dissymmetriccavities),1322 and helices1323−1325 have been reported. The solvent-dependent rearrangement of a macrocyclealong a thread has been shown to alter the CD response of a rotaxane(section 4.3.1).715 The position of a macrocycle has been usedto control the reactivity of a secondary alcohol toward esterificationin the presence of a chiral catalyst in a chemical information ratchet(section 4.4.1).809,810 Similarly, a chiraloptic switch has been reported based on a benzylicamide macrocycle and fumaramide/peptide stations (Figure 47).1285,1326 Photoisomerization-dependent relocation of the macrocycle to thepeptide station altered the CD response due to proximity-dependentmacrocycle–leucine residue interactions. A large reversibledifference in elliptical polarization response (>1500 deg cm2 dmol–1) was obtained upon isomerizationof thefumaramide station from E to Z.


Artificial Molecular Machines.

Erbas-Cakmak S, Leigh DA, McTernan CT, Nussbaumer AL - Chem. Rev. (2015)

(a)Chiraloptical switching upon photoinduced shuttling of themacrocycle between fumaramide (green) and peptide (orange) stations;the chiral center of the peptide station is highlighted by a blackcircle. (b) Percentage of E isomer calculated using 1H NMR (left y axis) and induced CD absorptionat 246 nm after alternating irradiation between 254 nm (half integer)and 312 nm (integers) (right y axis). Reprinted withpermission from ref (1326). Copyright 2003 American Chemical Society.
© Copyright Policy
Related In: Results  -  Collection

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getmorefigures.php?uid=PMC4585175&req=5

fig47: (a)Chiraloptical switching upon photoinduced shuttling of themacrocycle between fumaramide (green) and peptide (orange) stations;the chiral center of the peptide station is highlighted by a blackcircle. (b) Percentage of E isomer calculated using 1H NMR (left y axis) and induced CD absorptionat 246 nm after alternating irradiation between 254 nm (half integer)and 312 nm (integers) (right y axis). Reprinted withpermission from ref (1326). Copyright 2003 American Chemical Society.
Mentions: The responsive nature of induced circular dichroism makesit aninteresting phenomenon to study with the CD response of one specieschanging upon its interaction with another.387,1315−1319 The transformation of an achiral carbon center to a chiral one uponhydrogen-bonding-dependent symmetry breaking provided an early exampleof the influence of supramolecular interactions on chirality.1320 A number of chiral supramolecular assemblies,1315,1316,1321 chiral spaces (dissymmetriccavities),1322 and helices1323−1325 have been reported. The solvent-dependent rearrangement of a macrocyclealong a thread has been shown to alter the CD response of a rotaxane(section 4.3.1).715 The position of a macrocycle has been usedto control the reactivity of a secondary alcohol toward esterificationin the presence of a chiral catalyst in a chemical information ratchet(section 4.4.1).809,810 Similarly, a chiraloptic switch has been reported based on a benzylicamide macrocycle and fumaramide/peptide stations (Figure 47).1285,1326 Photoisomerization-dependent relocation of the macrocycle to thepeptide station altered the CD response due to proximity-dependentmacrocycle–leucine residue interactions. A large reversibledifference in elliptical polarization response (>1500 deg cm2 dmol–1) was obtained upon isomerizationof thefumaramide station from E to Z.

View Article: PubMed Central - PubMed

Affiliation: School of Chemistry, University of Manchester , Oxford Road, Manchester M13 9PL, United Kingdom.

AUTOMATICALLY GENERATED EXCERPT
Please rate it.

bonded molecules and on catenanes and rotaxanes in which switching of other protic solvents... This effect (listed in descending binding ability) stations on the thread, macrocycle In these systems, fast-responding reporters are preferred... practical applications by utilizing molecular scale changes to create macroscopic effects... The thread of these rotaxanes included an anthracene fluorophore similar application in synthetic polymers often furnishes a useful result... of Brownian motion can be exploited to great effect in the synthesis every aspect of functional molecule and materials design... An improved robotics” in which ratcheted motions of molecular components

No MeSH data available.


Related in: MedlinePlus