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Preparation and Reactions of Thiols

Preparation and Reactions of Thiols

Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.

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Updated: May 22, 2026

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

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Published on: August 19, 2012

Attach, remove, or replace: reversible surface functionalization using thiol-quinone methide photoclick chemistry.

Selvanathan Arumugam¹, Vladimir V Popik

¹Department of Chemistry, University of Georgia, Athens, 30602, United States.

Journal of the American Chemical Society

|May 10, 2012

Summary

This study introduces a facile method for light-directed surface patterning using photochemically generated o-naphthoquinone methides (oNQMs) and thiols. This technique enables reversible surface modification and precise control over substrate immobilization.

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Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance

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Published on: September 5, 2018

Area of Science:

Materials Science
Organic Chemistry
Surface Chemistry

Background:

Surface functionalization is crucial for various applications, including biosensing and microelectronics.
Existing methods often lack spatial control or require harsh conditions.
Photochemical reactions offer a promising route for precise surface modification.

Purpose of the Study:

To develop a facile and light-directed method for reversible surface derivatization and patterning.
To utilize the reaction between photochemically generated o-naphthoquinone methides (oNQMs) and thiols for surface modification.
To demonstrate the utility of this method for protein patterning and sequential immobilization strategies.

Main Methods:

A thiol-functionalized glass slide was treated with a substrate conjugated to 3-(hydroxymethyl)-2-naphthol (NQMP).
Irradiation via a shadow mask converted NQMP to reactive oNQM species, which reacted with surface thiols to form thioether links.
The method was applied to protein patterning using an NQMP-biotin conjugate and demonstrated orthogonality with azide click chemistry.

Main Results:

Efficient conversion of NQMP to oNQM and subsequent reaction with thiols to form stable thioether linkages.
Spatial control of surface derivatization was achieved due to the short lifetime of oNQM, preventing migration.
Successful protein patterning and development of a sequential click strategy for light-sensitive compound immobilization.
Demonstrated reversibility of the thioether linkage via UV irradiation for substrate removal or replacement.

Conclusions:

The oNQM-thiol reaction provides a versatile and efficient platform for light-directed surface patterning and modification.
This method offers precise spatial control, stability, and reversibility, making it suitable for advanced surface engineering.
The developed strategy is orthogonal to click chemistry, enabling complex sequential immobilization protocols.