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Updated: May 19, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Alkynylated phenazines: synthesis, characterization, and metal-binding properties of their bis-triazolyl cycloadducts
Jonathan J Bryant1, Yexiang Zhang, Benjamin D Lindner
1Organisch Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, Heidelberg 69120, Germany.
Abstract:
We have synthesized a series of ethynylated phenazines and their bis-triazolyl cycloadducts to serve as metal ion sensors. Binding of metal ions is achieved through coordination to the phenazine nitrogen atom and the triazole ring. To allow metal sensing in aqueous solution, the triazole units are substituted with water-soluble ethylene glycol chains. These phenazine cycloadducts exhibit a selective affinity for binding silver ions. Examination of the halogenated analogues reveals a lowering of the band gap and the corresponding bathochromic shifts in the absorption and emission spectra. The electron-withdrawing properties of these halogens also result in significantly decreased metal-binding activity of the phenazine cycloadducts.
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