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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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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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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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Photochemical Electrocyclic Reactions: Stereochemistry

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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Radical Formation: Homolysis00:54

Radical Formation: Homolysis

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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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Labeling DNA Probes03:31

Labeling DNA Probes

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DNA probes are fragments of DNA labeled with a reporter tag to enable their detection or purification. The resulting labeled DNA probes can then hybridize to target nucleic acid sequences through complementary base-pairing, and may be used to recover or identify these regions.
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Related Experiment Video

Updated: Nov 6, 2025

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

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A Self-Catalyzed Visible Light Driven Thiol Ligation.

Leona L Rodrigues1,2, Aaron S Micallef1,2, Michael C Pfrunder1,2

  • 1Centre for Materials Science, Queensland University of Technology, 2 George Street, Brisbane, Queensland 4000, Australia.

Journal of the American Chemical Society
|May 6, 2021
PubMed
Summary
This summary is machine-generated.

A novel visible light-induced ligation system generates thiophenols for rapid thiol-Michael additions. This additive-free, self-catalyzed method simplifies chemical synthesis and polymer modification.

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Polymer Chemistry

Background:

  • Conventional light-triggered thiol-ene/yne reactions often require additives like photocaged bases, organo-photocatalysts, or radical photoinitiators.
  • These additives can complicate reaction conditions and purification processes.

Purpose of the Study:

  • To develop a highly efficient, additive-free ligation system triggered by visible light.
  • To utilize a novel photoinduced rearrangement for generating reactive thiophenols.
  • To demonstrate the system's utility in polymer end-group modification.

Main Methods:

  • A visible light-induced rearrangement of *o*-thiopyrinidylbenzaldehyde (*o*TPyB) to generate thiophenol.
  • Self-catalyzed ligation via pyridine-mediated deprotonation of the photogenerated thiophenol.
  • Subsequent additive-free thiol-Michael addition with electron-deficient alkynes/alkenes.

Main Results:

  • The study describes the photoinduced rearrangement of *o*TPyB for the first time.
  • The ligation system operates efficiently in the absence of external additives.
  • Polymer end-group modification was successfully achieved with excellent end-group fidelity.

Conclusions:

  • The developed visible light-induced system offers an efficient and additive-free approach for thiol-Michael additions.
  • This method simplifies synthetic procedures and is applicable to polymer functionalization.
  • The self-catalyzed nature and visible light activation present a greener alternative for chemical ligations.