Advertisement

If you have an ACS member number, please enter it here so we can link this account to your membership. (optional)

ACS values your privacy. By submitting your information, you are gaining access to C&EN and subscribing to our weekly newsletter. We use the information you provide to make your reading experience better, and we will never sell your data to third party members.

ENJOY UNLIMITED ACCES TO C&EN

Synthesis

'Nindigo': A New Ligand Architecture

Treating the dye molecule indigo with substituted anilines leads to two diketimine binding sites in one ligand

by Sophie L. Rovner
September 13, 2010 | A version of this story appeared in Volume 88, Issue 37

By applying standard carbonyl-to-imine conversion chemistry to the famous dye molecule indigo, a team of chemists led by Robin G. Hicks of the University of Victoria, in British Columbia, has created a ligand with two β-diketimine metal-binding sites fused together in a bridging architecture (Chem. Commun. 2010, 46, 6753). The diketimine structural motif in which a pair of nitrogen atoms binds a metal is popular for its easy construction and for its tunability by using different alkyl or aryl substituent groups. But incorporating two diketimines in one ligand appears to be a chemical first, the researchers report. They treated indigo with various substituted anilines, titanium tetrachloride, and 1,4-diazabicyclo[2.2.2]octane in refluxing bromobenzene solvent to make indigo diketimine derivatives. The indigo-aniline reaction was actually described a century ago, Hicks notes, but until now a reproducible high-yield synthesis had not been reported. The researchers used the new class of ligands, which they have dubbed “Nindigo,” to make bispalladium complexes that are redox active and exhibit an intense near-infrared absorption.

Article:

This article has been sent to the following recipient:

0 /1 FREE ARTICLES LEFT THIS MONTH Remaining
Chemistry matters. Join us to get the news you need.