Related Experiment Video
Updated: Jun 18, 2026

09:28
Engineering Molecular Recognition with Bio-mimetic Polymers on Single Walled Carbon Nanotubes
Published on: January 10, 2017
Chirality in dynamic supramolecular nanotubes induced by a chiral solvent
Benjamin Isare1, Mathieu Linares, Loussiné Zargarian
1UPMC Univ Paris 06, UMR 7610, Chimie des Polymères, 75005, Paris, France.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 13, 2009
Summary
Chiral dynamic nanotubes form through a majority-rules effect, where monomer chirality dictates handedness. Chiral solvents influence the degree of chiral induction but not the overall helical bias.
Area of Science:
- Supramolecular Chemistry
- Polymer Science
- Chirality Studies
Background:
- Chirality amplification is observed in polymeric systems and dynamic supramolecular aggregates.
- Cooperative aggregation processes can couple chiral information if noncovalent interactions are balanced.
Purpose of the Study:
- Investigate chiral amplification in dynamic supramolecular nanotubes.
- Analyze the influence of monomer and solvent chirality on nanotube formation and handedness.
Main Methods:
- Synthesis of chiral bisurea monomers.
- Formation of dynamic nanotubes via self-assembly.
- Circular dichroism spectroscopy for chirality analysis.
- Competition experiments to compare chiral induction sources.
Main Results:
- A strong majority-rules effect governs the formation of chiral dynamic nanotubes from chiral bisurea monomers.
- Helical nanotubes with identical circular dichroism signatures were formed from racemic monomers in a chiral solvent.
- Monomer chirality determines nanotube handedness, irrespective of solvent chirality.
- Solvent chirality significantly impacts the extent of chiral induction.
Conclusions:
- Dynamic supramolecular nanotubes exhibit robust chiral amplification.
- The interplay between monomer and solvent chirality is crucial for controlling supramolecular chirality.
- This system provides a model for understanding chiral information transfer in self-assembling materials.
Related Concept Videos
Chirality at Nitrogen, Phosphorus, and Sulfur
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
Chirality
Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
Prochirality
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
Chirality in Nature
Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid. The...
Molecules with Multiple Chiral Centers
Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
Stereoisomerism of Cyclic Compounds
In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...

