Related Experiment Video

Updated: Dec 30, 2025

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

Planar Anthracene-Acetylene Frameworks as a Stereogenic Motif

Shinji Toyota¹, Hiroshi Ikeda^1,2, Tetsuo Iwanaga³

¹Department of Chemistry, School of Science, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo, 152-8551, Japan.

|January 22, 2020

Summary

Researchers created novel stereoisomers using rigid anthracene frameworks and acetylene linkers. These macrocyclic compounds offer new possibilities for studying π-conjugated systems.

Area of Science:

Organic Chemistry
Supramolecular Chemistry
Stereochemistry

Background:

Planar, rigid frameworks are crucial for designing complex molecular architectures.
Anthracene derivatives and acetylene linkers offer versatile building blocks for macrocycle synthesis.
Controlling stereochemistry in macrocyclic systems is essential for advanced material properties.

Purpose of the Study:

To synthesize and characterize novel stereoisomers using 1,8-substituted anthracene units and acetylene linkers.
To explore the generation of diastereomers, enantiomers, and topomers through strategic substituent placement.
To investigate the self-assembly behavior and potential applications of these macrocyclic frameworks.

Main Methods:

Synthesis of macrocyclic compounds via coupling reactions of 1,8-substituted anthracene building blocks.
Spectroscopic techniques (NMR, Mass Spectrometry, etc.) for structural and stereochemical elucidation.
Theoretical calculations to understand molecular properties and stereochemical outcomes.
Scanning tunneling microscopy (STM) to study self-assembly at the liquid-solid interface.

Main Results:

Successfully synthesized various stereoisomers (diastereomers, enantiomers, topomers) of planar, rigid macrocyclic frameworks.
Demonstrated the ability to control stereochemistry by modifying linker combinations and substituent patterns.
Observed conglomerate-type self-assembly of a prochiral cyclic dimer into a monolayer via STM.
Characterized the molecular structures, stereochemistry, and properties of the synthesized compounds.

Conclusions:

The designed macrocyclic frameworks provide a versatile platform for generating diverse stereoisomers.
Strategic modification of linkers and substituents enables precise control over molecular stereochemistry.
The observed self-assembly behavior highlights the potential of these π-conjugated macrocycles in supramolecular chemistry and materials science.

Keywords:

alkynes anthracene self-assembly stereochemistry structure elucidation

More Related Videos

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

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...

Aromatic Hydrocarbon Anions: Structural Overview

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...

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,...

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.

Radicals: Electronic Structure and Geometry

Radicals: Electronic Structure and Geometry

This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...

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

Efficacy of Radial Pressure Wave Therapy Combined With Exercise in Physically Active Athletes With Patellar Tendinopathy: A Randomized Controlled Trial.

Translational sports medicine·2026

p-Type Organic Semiconductors With an Annulated Thiazole: Photochemical Synthesis and Theoretically High Hole Mobility Predicted From Crystal Structure.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026

Prediction of Human Serum Concentration-Time Profiles of Golimumab and Ustekinumab Using Pharmacokinetic Data From Common Marmosets With Assessment of Anti-Drug Antibodies.

Biopharmaceutics & drug disposition·2026

Effect of Alumina Airborne-Particle Abrasion Followed by Plasma Treatment on Bond Strength of Dental PEEK to MMA-Based Luting Systems.

Bioengineering (Basel, Switzerland)·2026

Phenotypic and genetic variation among Rhododendron arboreum species complex widely distributed throughout the Himalayas suggests an obscure geographic origin of the clade.

Annals of botany·2026

Therapeutic Effects of Capacitive and Resistive Monopolar Radiofrequency on Muscle Stiffness and Local Hemodynamics of the Rectus Femoris: A Randomized Crossover Study of Female University Soccer Players.

International journal of sports physical therapy·2026

See all related articles