Issue 5, 2016

A simple route to phosphamethine cyanines from S,N-heterocyclic carbenes

Abstract

Although salts of thiazolium cations are known, many readily prepared iodide salts have eluded spectroscopic and structural characterization; herein, data for a variety of such salts are reported. It has been demonstrated that thiazolium cations can be deprotonated to generate S,N-heterocyclic carbenes and their “electron rich olefin” dimers, but use of the former has been largely overshadowed by that of the more common N-heterocyclic carbenes. We report herein that the deprotonation of thiazolium iodides and their subsequent reaction with a conveniently prepared triphosphenium precursor grants phosphamethine cyanine cations with solid-state geometry and electronic structure unlike those of NHC-stabilized cations. Protection of the phosphorus atom in such ions with elemental sulfur provides an air- and moisture-stable dithiophosphinium salt.

Graphical abstract: A simple route to phosphamethine cyanines from S,N-heterocyclic carbenes

Supplementary files

Article information

Article type
Paper
Submitted
06 août 2015
Accepted
28 oct. 2015
First published
29 oct. 2015

Dalton Trans., 2016,45, 2138-2147

Author version available

A simple route to phosphamethine cyanines from S,N-heterocyclic carbenes

J. F. Binder, A. M. Corrente and C. L. B. Macdonald, Dalton Trans., 2016, 45, 2138 DOI: 10.1039/C5DT03019F

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