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Preparation of 1° Amines: Azide Synthesis

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...

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The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...

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Fabricating Reactive Surfaces with Brush-like and Crosslinked Films of Azlactone-Functionalized Block Co-Polymers

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Published on: June 30, 2018

Development of Low Temperature Activatable Aryl Azide Adhesion Promoters as Versatile Surface Modifiers.

Alexandros A Atzemoglou^1,2, Niccolò Bartalucci¹, Felix Donat³

¹SuSoS AG, Lagerstrasse 14, Dübendorf 8600, Switzerland.

ACS Applied Engineering Materials

|May 1, 2025

Summary

This summary is machine-generated.

Researchers developed new adhesion promoters using substituted aryl azides for gentle surface modification. These compounds enable stable chemical bridging at temperatures below 100 °C, overcoming limitations of existing methods for immobilizing polymeric films.

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Area of Science:

Materials Science
Organic Chemistry
Surface Chemistry

Background:

Adhesion promoters create chemical bridges for permanent surface modification.
Existing methods using perfluoro-aryl azides require high temperatures (>100 °C) or are photolytically unfeasible.
There is a need for adhesion promoters that activate at lower temperatures for broader material compatibility.

Purpose of the Study:

To design and synthesize novel aryl azides with tunable, lower activation temperatures.
To enable covalent attachment of polymers lacking reactive groups to surfaces under mild conditions.
To demonstrate the efficacy of these new adhesion promoters for surface functionalization.

Main Methods:

Computational modeling using density functional theory (DFT) to predict activation temperatures.
Synthesis of three substituted aryl azide molecules.
Experimental validation of thermal activation temperatures and C-H insertion reactions.
Incorporation of synthesized molecules into polymeric backbones to create adhesion promoters.
Surface functionalization with polyvinylpyrrolidone (PVP) films.
Characterization using spectroscopic ellipsometry (ELM) and X-ray photoelectron spectroscopy (XPS).

Main Results:

Substituent variation effectively tunes aryl azide activation temperatures below 100 °C.
The difluoro-substituted p-phenoxy azide demonstrated reactivity around 70 °C via C-H insertion.
Synthesized adhesion promoters facilitated covalent attachment of PVP films to substrates.
Successful immobilization of PVP films under mild thermal activation conditions was confirmed.

Conclusions:

Novel aryl azides offer a pathway to low-temperature surface functionalization.
The developed adhesion promoters enable robust covalent attachment of polymers to various surfaces.
This approach expands the utility of adhesion promoters for sensitive materials and applications, including medical devices.