Synthesis Of Anthraquinone Derivatives Via Click Chemistry And The Studies On Their Properties

In the field of supramolecular chemistry, the functionally modified of anthraquinone have beenplaying an important role. Because of the unique fluorescent characteristic of the anthraquinone. with thebasic principle of molecular design, we introduced theTetrathiafulvalene to the anthraquinone framework.This research mainly synthesized three series of anthraquinone derivatives, Garried out of the design,synthesis, characterization and recognition properties of new anthraquinone based receptors, Main contentof this paper are as follows:1. A series of anthraquinone-tetrathiafulvalene derivatives were designed and synthesized, and theirchemical structures were characterized by¹H NMR,¹³C NMR、FT-IR、MS （MALDI-TOF） and elementaryanalysis. Because anthraquinone-TTF are well-established electroactive unit. So the identificationproperties of target compounds12toward Zn²⁺、Cu²⁺、Hg²⁺、Cd²⁺、Ag⁺ions were studied by cyclicvoltammetry（CV）. We study of target compounds12toward Li⁺、Na⁺、K⁺、Cu²⁺、Mn²⁺、Co²⁺、Al³⁺、Ni²⁺、Fe²⁺、Hg²⁺、Ba²⁺、Cd²⁺、Pb²⁺、Zn`2+and Cr³⁺ions were recognized by ultraviolet photometric titration.At the same time, we study of target compounds13toward Al³⁺、Cd²⁺、Pb²⁺、Zn²⁺、Ag⁺and Sc³⁺ ions wereelectron transfer by ultraviolet photometric titration. Also use fluorescence titration experiment show thattarget compound12to have strong recognition ability when Al³⁺was added. Hence, target compound canbe used as a new fluorescent sensor for the Al³⁺ ion.2. A series of anthraquinone-naphthalene derivatives were designed and synthesized, and theirchemical structures were characterized by¹H-NMR,¹³C NMR、 FT-IR、MS （MALDI-TOF） andelementary analysis. The recognition properties of target compounds16and19for cations wereinvestigated using different methods including and cyclic voltammetry and fluorescence titration. Theidentification properties of target compounds16and19toward Zn²⁺、Cu²⁺、Hg²⁺、Cd²⁺、Al³⁺、Na⁺cationswere recogised by cyclic voltammetry（CV）. Fluorescence titration experiment show that target compound16and19to have strong recognition ability when Al³⁺was added. Hence, target compound can be used asa new fluorescent sensor for the Al³⁺ ion.3. The sequent reaction of22with1,8-bis（prop-2-ynyloxy）anthraquinone11at the presence of the catalyst of CuSO4/VcNa gave a novel anthraquinone-based thiacalixarene compound23, which wascharacterized by¹H NMR, MS （MALDI-TOF）, FT-IR and elementary analysis. The fluorescence titrationexperiments have shown that compound23has a good selectivity with Al³⁺and the complexation of23with Al³⁺ in a1:2complex mode gives an enhanced fluorescence change at559nm. In the CHCl₃-CH₃CN（V:V,3:1） solvents, the binding constant for the complex of23and Al³⁺ is2670mol/L. at room temperature.Hence, target compound23can be used as a new fluorescent sensor for the Al³⁺ ion.