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A supramolecular helix that disregards chirality.
- Source :
-
Nature chemistry [Nat Chem] 2016 Jan; Vol. 8 (1), pp. 80-9. Date of Electronic Publication: 2015 Nov 16. - Publication Year :
- 2016
-
Abstract
- The functions of complex crystalline systems derived from supramolecular biological and non-biological assemblies typically emerge from homochiral programmed primary structures via first principles involving secondary, tertiary and quaternary structures. In contrast, heterochiral and racemic compounds yield disordered crystals, amorphous solids or liquids. Here, we report the self-assembly of perylene bisimide derivatives in a supramolecular helix that in turn self-organizes in columnar hexagonal crystalline domains regardless of the enantiomeric purity of the perylene bisimide. We show that both homochiral and racemic perylene bisimide compounds, including a mixture of 21 diastereomers that cannot be deracemized at the molecular level, self-organize to form single-handed helical assemblies with identical single-crystal-like order. We propose that this high crystalline order is generated via a cogwheel mechanism that disregards the chirality of the self-assembling building blocks. We anticipate that this mechanism will facilitate access to previously inaccessible complex crystalline systems from racemic and homochiral building blocks.
- Subjects :
- Circular Dichroism
Crystallization
Macromolecular Substances
Magnetic Resonance Spectroscopy
Molecular Structure
Perylene chemical synthesis
Perylene chemistry
Phase Transition
Solutions
Spectrophotometry, Ultraviolet
Stereoisomerism
X-Ray Diffraction
Imides chemical synthesis
Imides chemistry
Models, Molecular
Perylene analogs & derivatives
Subjects
Details
- Language :
- English
- ISSN :
- 1755-4349
- Volume :
- 8
- Issue :
- 1
- Database :
- MEDLINE
- Journal :
- Nature chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 26673268
- Full Text :
- https://doi.org/10.1038/nchem.2397