Reversible Optical Transcription of Supramolecular Chirality into Molecular Chirality

@article{deJong2004ReversibleOT,
  title={Reversible Optical Transcription of Supramolecular Chirality into Molecular Chirality},
  author={Jaap J D de Jong and Linda Nienke Lucas and Richard M Kellogg and Jan H. van Esch and Ben L. Feringa},
  journal={Science},
  year={2004},
  volume={304},
  pages={278 - 281}
}
In nature, key molecular processes such as communication, replication, and enzyme catalysis all rely on a delicate balance between molecular and supramolecular chirality. Here we report the design, synthesis, and operation of a reversible, photoresponsive, self-assembling molecular system in which molecular and supramolecular chirality communicate. It shows exceptional stereoselectivity upon aggregation of the molecules during gel formation with the solvent. This chirality is locked by… Expand

Topics from this paper

Supramolecular chirality in self-assembled soft materials: regulation of chiral nanostructures and chiral functions.
TLDR
This research news report reports the recent development in the regulation of chiral nanostructures in soft gels or vesicle materials and develops several new functions pertaining to the soft gel materials, which single chiral molecules could not perform. Expand
Gelation induced supramolecular chirality: chirality transfer, amplification and application.
TLDR
In this review, recent progress in gelation-induced supramolecular chirality is discussed and the development of the "smart" chiral materials such as chiroptical devices, catalysts and chiral sensors is discussed. Expand
Inversion of the Supramolecular Chirality of Nanofibrous Structures through Co-Assembly with Achiral Molecules.
TLDR
This work exemplifies a feasible method to invert the helicity of chiral nanostructures by the addition of achiral molecules, but also provides a method to explore their functions in environments where chiral and a chiral molecules are in close proximity. Expand
Supramolecular Chiroptical Switches Based on Achiral Molecules
Chirality plays an important role in biological and material sciences. By introducing chiral elements into functional materials, new properties are created and an increase in information density canExpand
Supramolecular chiroptical switches.
TLDR
This review summarizes the recent progress in the construction of supramolecular chiroptical switchable systems that reversibly respond to various stimuli, such as light, electricity, magnetic fields, mechanical force, solvents, pH, temperature, and chemical additives. Expand
Dynamic Modulation of Supramolecular Chirality Driven by Factors from Internal to External Levels.
TLDR
Through dynamic modulation with changes in chiroptical spectroscopy and electron microscopy, the mechanism of formation of supramolecular chirality is elaborated and the ingenious dynamic modulation of chiral nanostructures by these factors is focused on. Expand
Helicity Inversion of Supramolecular Hydrogels Induced by Achiral Substituents.
Probing the supramolecular chirality of assemblies and controlling their handedness are closely related to the origin of chirality at the supramolecular level and the development of smart materialsExpand
Autoamplification of molecular chirality through the induction of supramolecular chirality.
TLDR
The novel concept for the autoamplification of molecular chirality, wherein the amplification proceeds through the induction of supramolecular chirability, is presented and the product is enriched in the template enantiomer. Expand
Gelating-induced supramolecular chirality of achiral porphyrins: chiroptical switch between achiral molecules and chiral assemblies.
TLDR
A thermo-driven supramolecular chiroptical switch was proposed through the switch between achiral molecule and chiral molecular assemblies to form organogels using chiral porphyrins employed as functional compounds. Expand
Light-Driven Chiral Switching of Supramolecular Metallacycles with Photoreversibility
Summary The construction of artificial chiral self-assembled systems has evolved to be one of the most attractive topics within supramolecular chemistry and materials science. However,Expand
...
1
2
3
4
5
...

References

SHOWING 1-10 OF 15 REFERENCES
Helical self-assembled polymers from cooperative stacking of hydrogen-bonded pairs
TLDR
This work describes a general strategy for the design of functionalized monomer units and their association in either water or alkanes into non-covalently linked polymeric structures with controlled helicity and chain length. Expand
Chiral architectures from macromolecular building blocks.
The chiral architectures from macromolecular building blocks were discussed. The conformational dynamics of the helicity and their effect on the (photo)physical properties of the polymers and theExpand
Controlling molecular self-organization: formation of nanometer-scale spheres and tubules
TLDR
Crystallographic studies revealed how metal ion coordination and substrate recognition direct the formation of these supramolecular assemblies, and the addition of greater amounts of pyridine N-oxide changed the curvature of the assembling surface and resulted in theformation of extended tubules. Expand
Supramolecular chemistry
  • J. Lehn
  • Chemistry, Medicine
  • Science
  • 1993
The article discusses molecular recognition and overviews the key concepts -storage and retrieval of chemical information by molecular structures, supramolecular reagents and catalysts, molecularExpand
Toward Self-Organization and Complex Matter
  • J. Lehn
  • Chemistry, Medicine
  • Science
  • 2002
Beyond molecular chemistry based on the covalent bond, supramolecular chemistry aims at developing highly complex chemical systems from components interacting through noncovalent intermolecularExpand
Reversible Diastereoselective Photocyclization of a Diarylethene in a Single-Crystalline Phase
Optically active photochromic (S)- and (R)-1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(3-methyl-1-penten-1-yl)-5-phenyl-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopentenes ((S)-1a and (R)-1a) were synthesized.Expand
Control of the thermal cis to trans isomerizations of azobenzene and thioindigo derivatives by the formation of supramolecular H-bonded assemblies
2,3-Bis(aminocyclohexyl)−6-methoxy-1,3,5-triazine (1a) forms intermolecular H-bonded complexes with 3,3′-diacetyl-cis-azoenzene (4) and 6,6′-diethoxy-cis-thioindigo (5b), (association constants K =Expand
A field guide to foldamers.
TLDR
I. Foldamer Research 3910 A. Backbones Utilizing Bipyridine Segments 3944 1. Expand
"J."
however (for it was the literal soul of the life of the Redeemer, John xv. io), is the peculiar token of fellowship with the Redeemer. That love to God (what is meant here is not God’s love to men)Expand
...
1
2
...