Related Experiment Video
Updated: Feb 10, 2026

Synthesis of Wavelength-shifting DNA Hybridization Probes by Using Photostable Cyanine Dyes
Published on: July 6, 2016
Synthesis, Spectroscopic Characterization, and Redox Reactivity of a Cyclic (Alkyl) Amino Carbene-Derived Arsamethine
Kortney M Melancon1, M Brenton Gildner1, Todd W Hudnall1
1Department of Chemistry and Biochemistry, Texas State University, 601 University Dr., San Marcos, TX, 78666, USA.
Abstract:
In our efforts to prepare a diarsenic allotrope supported by two cyclic alkyl amino carbene (CAAC) ligands we stumbled upon the synthesis of the first carbene-supported chloroarsinidene 3, which has been fully characterized by a combination of NMR spectroscopic and XRD methods. Although further reduction of 3 was not possible, we found that addition of a second equivalent of CAAC in refluxing toluene afforded the first example of a crystallographically characterized arsamethine cyanine dye (4). The arsenic(I) dye is structurally similar to phosphorus analogues, and contains an arsenide anion with two stereochemically active lone pairs supported by two iminium ligands. The UV/Visible spectrum and redox chemistry of 4 were also explored. Upon reduction with one equivalent of KC8 , 3 is reduced to the originally targeted CAAC2 As2 allotrope 6, whereas oxidation provides access to the first example of an arsenic(II) radical dication (5).
More Related Videos
19:58Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
09:46Synthesis of Plant Phenol-derived Polymeric Dyes for Direct or Mordant-based Hair Dyeing
Published on: December 1, 2016
Related Concept Videos
Amino acids
Balancing Redox Equations
Synthesis and Decomposition Reactions
Redox Reactions
Redox Reactions
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis