Related Experiment Video
Updated: May 29, 2026
08:07
A Micropatterning Assay for Measuring Cell Chirality
Published on: March 11, 2022
Tailoring homochirality at surfaces: going beyond molecular handedness
Matthew Forster1, Matthew S Dyer, Mats Persson
1Surface Science Research Centre and Department of Chemistry, University of Liverpool, Oxford Street, Liverpool L69 3BX, UK.
Journal of the American Chemical Society
|September 3, 2011
Summary
Researchers engineered a homochiral surface by modifying proline molecules. This structural change controlled molecular
Area of Science:
- Surface science
- Chirality studies
- Molecular self-assembly
Background:
- Chirality at surfaces is typically described by molecular handedness.
- Adsorption can create chiral 'footprints,' adding another layer of complexity to surface chirality.
- Achieving a truly homochiral surface requires control over both molecular handedness and footprint chirality.
Purpose of the Study:
- To engineer a homochiral surface by controlling adsorption footprints.
- To demonstrate that modifying molecular structure can dictate surface chirality.
- To create a truly homochiral interface with uniform chirality.
Main Methods:
- Structural modification of enantiopure (S)-proline to 3-pyrroline-2-carboxylic acid (PCA).
- Characterization using scanning tunneling microscopy (STM) for single-molecule imaging.
- Analysis via reflection absorption infrared spectroscopy (RAIS) and density functional theory (DFT) calculations.
Main Results:
- Modified proline (PCA) induced homochiral footedness in the (4 × 2) assembly on Cu(110).
- The structural modification successfully transformed heterochiral footprints to homochiral ones.
- A truly homochiral interface was achieved by controlling both molecular and footprint chirality.
Conclusions:
- Controlling adsorption footprints is crucial for tailoring surface chirality.
- Molecular modifications can precisely dictate the chiral organization at interfaces.
- This approach offers a pathway to engineer functional organic-inorganic interfaces with controlled chirality.
More Related Videos
Related Concept Videos
02:05Prochirality
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...
02:30Chirality 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...
02:25Chirality
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...
02:25Molecules 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...
02:30Chirality 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...
02:34Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.