Synthesis of (thia)calixarene-based exTTF derivatives and their electron transfers towards p-chloranil and C₆₀

Abstract

Two novel (thia)calixarene-based exTTF derivatives(3a and 3b) were prepared by Mitsunobu reactions in toluene using diethyl azodicarboxylate(DEAD) and triphenylphosphine(PPh₃) system. The cyclic voltammograms of compounds 3a and 3b were provided, and two electron-irreversible waves with redox potentials were observed. Meanwhile, the intermolecular electron transfer(ET) properties of both compounds 3a and 3b towards p-chloranil(Q) and C₆₀ were investigated via UV-Vis and fluorescent spectroscopies, respectively. The results indicated that the introduced nonoxidable metal ions(Al³⁺, Pb²⁺, Sc³⁺) might promote the intermolecular ET from compounds 3a and 3b towards Q ensembles, whereas the effects of Sc³⁺ were the most impressive. Furthermore, the effects of the same metal ions(Al³⁺, Pb²⁺, Sc³⁺) added for compound 3b were greater than those for compound 3a. Additionally, the photoinduced intermolecular ET from compounds 3a and 3b towards C₆₀ was observed.

Keywords

exTTF / Calix[4]arene / Thiacalix[4]arene / p-Chloranil(Q) / C₆₀ / Electron transfer

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