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J Org Chem. 2012 Mar 2;77(5):2441-5. doi: 10.1021/jo300101c. Epub 2012 Feb 14.

Dual signaling system with an extended-tetrathiafulvalene-phenanthroline dyad acting as an electrooptical cation chemosensor.

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L'UNAM Université, Université d'Angers, Laboratoire MOLTECH-Anjou, CNRS UMR 6200, 2 Bd Lavoisier, 49045 Angers, France.


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 (Fe(2+), Ni(2+), and Zn(2+)) and also with varied cations such as Ca(2+) and Pb(2+) is presented.

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