Synthesis, Spectroscopic Characterization, and Redox Reactivity of a Cyclic (Alkyl) Amino Carbene-Derived Arsamethine Cyanine Dye.

Autor: Melancon KM; Department of Chemistry and Biochemistry, Texas State University, 601 University Dr., San Marcos, TX, 78666, USA., Gildner MB; Department of Chemistry and Biochemistry, Texas State University, 601 University Dr., San Marcos, TX, 78666, USA., Hudnall TW; Department of Chemistry and Biochemistry, Texas State University, 601 University Dr., San Marcos, TX, 78666, USA.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2018 Jul 02; Vol. 24 (37), pp. 9264-9268. Date of Electronic Publication: 2018 Jun 05.
DOI: 10.1002/chem.201802393
Abstrakt: 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 KC 8 , 3 is reduced to the originally targeted CAAC 2 As 2 allotrope 6, whereas oxidation provides access to the first example of an arsenic(II) radical dication (5).
(© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
Externí odkaz:
Nepřihlášeným uživatelům se plný text nezobrazuje