Cyclic voltammogram analysis of the 3,3´- (1,4-phenylene) perchlorates

ahmad alkawaldeh, A. Jafari
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Abstract

As a consequence of a three-stage synthesis from terephthalic aldehyde, a series of 3,3 '- (1,4-phenylene) perchlorates including methyl, hydrogen, acetyl, bromio, methoxy and nitro groups (R = Br, H, Me). The matching formazans were reacted with formalin in dioxane in the presence of perchloric acid to produce tetrazin ium salts. Formazans were synthesized by reacting terephthalic aldehyde phenylhydrazone with ar ene diazonium tosylates in a DMF/pyridine combination. The use of ar ene diazonium tosylates greatly simplified the separation and purification of formazans. The p henylhydrazone was produced in aqueous dioxane using the usual approach from terephthalic aldehyde and phenylhydrazine/hydrochloric acid. Individual f ormazans and tetrazinium perchlorates were isolated and characterized by elemental analysis, IR, NMR, UV spectroscopy. The electrochemical reduction of tetrazinium perchlorates was investigated using cyclic voltammetry (CV). Thus, all salts in the cathode region have two one-electron reduction peaks, which are connected to the sequential production of a radical cation and a biradical. It was discovered that donor substituents (R: OMe, Me) in the aromatic ring at position 1 accelerate tetrazinium cation reduction, whereas acceptor substituents (R: NO2, COMe,) inhibit this process. On this premise, it was proposed that in the presence of donor substituents in the aromatic ring at position 1, the matching bis-verdazyl radicals should be easily generated. As a result, 3,3'- (1,4-phenylene) perchlorates are possible antecedents of symmetric biradical systems based on verdazyl radicals.
3,3′-(1,4-苯基)高氯酸盐的循环伏安分析
由对苯二甲酸醛经三步合成,得到一系列3,3 '-(1,4-苯基)高氯酸盐,包括甲基、氢、乙酰基、溴基、甲氧基和硝基(R = Br, H, Me)。在高氯酸存在下,将匹配的甲醛与福尔马林在二氧六环中反应生成四氮铵盐。在DMF/吡啶的组合下,对苯二甲酸乙二醛苯腙与甲苯重氮酸盐反应合成了甲醛酰胺。甲苯基重氮酸盐的使用大大简化了甲醛的分离和纯化。以对苯二甲酸醛和苯肼/盐酸为原料,在二氧六环水溶液中制备了对苯基腙。通过元素分析、红外光谱、核磁共振光谱、紫外光谱等方法对呋喃三甲酸酯和高氯酸四锌进行了分离和表征。采用循环伏安法研究了高氯酸四锌的电化学还原。因此,阴极区的所有盐都有两个单电子还原峰,这两个峰与自由基阳离子和双自由基的顺序产生有关。发现芳香环1位的供体取代基(R: OMe, Me)加速了四锌离子的还原,而受体取代基(R: NO2, COMe,)抑制了这一过程。在此前提下,提出芳香环1位存在供体取代基时,容易生成匹配的双硫代基自由基。因此,3,3'-(1,4-苯基)高氯酸盐可能是基于硫酰自由基的对称双自由基体系的前体。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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