Related Experiment Video
Updated: Jul 9, 2026
09:30
The Synthesis of RGD-functionalized Hydrogels as a Tool for Therapeutic Applications
Published on: October 7, 2016
Synthesis of functionalised aromatic oligamide rods
Jeffrey Plante1, Fred Campbell, Barbora Malkova
1School of Chemistry, University of Leeds, Woodhouse Lane, Leeds, LS29JT, United Kingdom. A.J.Wilson@leeds.ac.uk.
Organic & Biomolecular Chemistry
|December 14, 2007
Summary
Synthetic chemists created rod-shaped foldamers using a modular approach. This method allows specific side-chain placement, influencing molecular shape through hydrogen bonds.
Area of Science:
- Synthetic chemistry
- Molecular design
- Supramolecular chemistry
Background:
- Designing molecules with predictable shapes is a key challenge in synthetic chemistry.
- Foldamers are molecules that adopt well-defined conformations.
Purpose of the Study:
- To develop a modular strategy for synthesizing rod-shaped para-oligobenzamide foldamers.
- To enable regiospecific incorporation of side chains onto the foldamer scaffold.
Main Methods:
- A modular synthetic approach was employed.
- Side chains were incorporated via a phenolic ether linkage.
- Intramolecular hydrogen bonding was utilized to influence conformation.
Main Results:
- Successfully synthesized rod-shaped para-oligobenzamide molecules.
- Demonstrated regiospecific attachment of side chains.
- Observed conformational restriction due to intramolecular hydrogen bonding.
Conclusions:
- The developed modular approach provides a versatile method for constructing conformationally restricted foldamers.
- This strategy facilitates the design of precisely shaped molecules for potential applications in materials science and nanotechnology.
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Related Concept Videos
01:11Aryldiazonium Salts to Azo Dyes: Diazo Coupling
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
01:11ortho–para-Directing Activators: –CH3, –OH, –NH2, –OCH3
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
01:19Diazonium Group Substitution: –OH and –H
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
01:10Nomenclature of Aryl and Heterocyclic Amines
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
01:19Amines to Amides: Acylation of Amines
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
01:20Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...