Dual Signaling System with an Extended-Tetrathiafulvalene–Phenanthroline Dyad Acting as an Electrooptical Cation Chemosensor

• Published in: Journal of organic chemistry 2012-03, Vol.77 (5), p.2441-2445
• Main Authors: Hardouin-Lerouge, Marie, Chesneau, Bertrand, Allain, Magali, Hudhomme, Piétrick
• Format: Article
• Language: English
• Subjects: Analytical chemistry; Cations - chemistry; Chemical Sciences; Chemistry; Crystallography, X-Ray; Exact sciences and technology; Fluorescent Dyes - chemistry; General, instrumentation; Heterocyclic compounds; Heterocyclic Compounds - chemistry; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Models, Molecular; Molecular Structure; Noncondensed benzenic compounds; Organic chemistry; Phenanthrolines - chemistry; Preparations and properties
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo300101c

An efficient synthesis of unprecedented fused extended-tetrathiafulvalene–dipyridoquinoxaline (exTTF-dpq) dyad is described through the Horner–Wardsworth–Emmons olefination methodology from the dipyrido­[3,2-a:2′,3′-c]-benzo­[3,4]­phenazine-11,16-quinone (NqPhen) ligand starting material. This exTTF-dpq dyad is demonstrated to act as a dual redox and colorimetric sensor for cations exploiting the proximity between the redox tetrathiafulvalene and the optical phenanthroline detecting sites. Its ability for sensing cations from the d-group metal transitions (Fe2+, Ni2+, and Zn2+) and also with varied cations such as Ca2+ and Pb2+ is presented.