Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Prochirality

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

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...

Molecules with Multiple Chiral Centers

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...

Chirality at Nitrogen, Phosphorus, and Sulfur

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...

Stereoisomerism of Cyclic Compounds

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,...

Chirality in Nature

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.

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

One-Pot, One-Step Mn-bis(imino)pyridine Complexes through Sonochemistry.

Inorganic chemistry·2026

Same author

Structures of nickel-, copper-, and zinc-salophen derivatives.

Acta crystallographica. Section C, Structural chemistry·2026

Same author

Hydrodefluorination of a Fluorobenzene Equivalent by Harnessing a P(III)/Pd(II)-P(V)/Pd(0) Redox Couple Using a P-CF<b><sub>3</sub></b>-Functionalized Benzazaphosphole.

Inorganic chemistry·2026

Same author

A General Sonogashira-Type Strategy for Exopolyhedral B-C(sp) Bond Formation on <i>o</i>- and <i>m</i>-Carboranes.

Organic letters·2026

Same author

Stable Negatively Curved Polycyclic Hydrocarbon Radical: A Molecular Segment of Magnetic Carbon Schwarzite.

Journal of the American Chemical Society·2026

Same author

Fragment-Based Online OzESI-MS, NMR, and Computational DP4+/DFT Approaches to the Characterization of the Putative Biosynthetic Lipid Precursor of Atkamine from Alaskan <i>Latrunculia</i> Sponges.

ACS omega·2026

Search research articles

Related Experiment Video

Updated: Jan 13, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Chiral Semibuckminsterfullerene: Synthesis, Resolution, and Chiroptical Properties.

Cody F Dickinson¹, Xiaoqi Tian², Justin K Yang¹

¹Department of Chemistry, University of Hawaii at Manoa, 2545 McCarthy Mall, Honolulu, Hawaii 96822, United States.

Organic Letters

|October 28, 2025

Summary

Researchers developed a gram-scalable synthesis for C30-buckybowls and achieved the first desymmetrization to a chiral semifullerene. This breakthrough enables practical production of these complex molecules for advanced material applications.

More Related Videos

$Measurements of Long-range Electronic Correlations During Femtosecond Diffraction Experiments Performed on Nanocrystals of Buckminsterfullerene$

Measurements of Long-range Electronic Correlations During Femtosecond Diffraction Experiments Performed on Nanocrystals of Buckminsterfullerene

Published on: August 22, 2017

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Published on: February 7, 2017

Related Experiment Videos

Last Updated: Jan 13, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

$Measurements of Long-range Electronic Correlations During Femtosecond Diffraction Experiments Performed on Nanocrystals of Buckminsterfullerene$

Measurements of Long-range Electronic Correlations During Femtosecond Diffraction Experiments Performed on Nanocrystals of Buckminsterfullerene

Published on: August 22, 2017

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Published on: February 7, 2017

Area of Science:

Organic Chemistry
Supramolecular Chemistry
Materials Science

Background:

Fullerenes and buckybowls are unique carbon nanomaterials with intriguing electronic and optical properties.
Chiral semifullerenes offer potential for stereoselective applications but are challenging to synthesize.
Developing scalable synthetic routes is crucial for exploring their practical utility.

Purpose of the Study:

To establish a gram-scalable synthesis of C30-buckybowls and their derivatives.
To report the first successful desymmetrization of a buckybowl to a chiral semifullerene.
To characterize the chiroptical and electronic properties of the synthesized chiral compounds.

Main Methods:

Optimization of a synthetic route for gram-scale production of buckybowl precursors.
Development of a novel desymmetrization strategy to access chiral semifullerenes.
Experimental and theoretical determination of chiroptical (e.g., circular dichroism) and electronic properties.

Main Results:

Successful gram-scale synthesis of C30-buckybowl precursor 1 and derivative 2.
Demonstration of the first desymmetrization yielding a stable chiral semifullerene.
Comprehensive characterization of the synthesized compounds' unique properties.

Conclusions:

The developed process allows for practical, gram-scale production of valuable buckybowls and chiral semifullerenes.
Chiral hemifullerenes represent promising scaffolds for stereoselective ligands, receptors, sensors, and catalysts.
These findings pave the way for the development of new advanced materials based on curved aromatic systems.