Anodic Oxidation of 2,6-Dihydroxynaphthalene1 and Structural Characterization of the Oligomers
Anodic Oxidation of 2,6-Dihydroxynaphthalene1 and Structural Characterization of the Oligomers
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2,6-二羟基萘1的阳极氧化及低聚物的结构表征
DOI：
10.1021/jo00094a045
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发表时间：
1994
影响因子：
3.6
通讯作者：
V. Horák
中科院分区：
文献类型：
--
作者：
G. Marin;V. Horák
采用电位控制电化学氧化法对2，6-二羟基萘（1）进行氧化，得到了两种齐聚物，并通过光谱（1H和13 C NMR，IR和UV）和电化学（CV）方法对其进行了表征。1 H NMR化学位移的过乙酰基衍生物，其中显示不同的值的乙酰氧基连接在末端和内部的位置的链，是必不可少的产品的结构测定。单体1a、二聚体2a和两种立体异构三聚体3a和4a的全乙酰基衍生物作为低聚物的光谱表征和结构测定中的模型。从阳极电解液中分离的产物是由平均9个单体单元组成的低聚物5的混合物。从阳极6提取的产物的光谱数据表明其分子量高得多。在所有研究的化合物中，萘环被证明是在1-和5-位连接。这两种低聚物的溶解度和光谱数据表明，链没有交联。聚（2，6-二羟基萘）薄膜的循环伏安行为与文献报道的聚（2，6-二羟基萘）薄膜的循环伏安行为相似
Potential-controlled electrochemical oxidation of 2,6-dihydroxynaphthalene (1) produced two oligomers, which were characterized by spectrometric ( 1 H and 13 C NMR, IR, and UV) and electrochemical (CV) methods. The 1 H NMR chemical shifts of the peracetyl derivatives, which showed different values for the acetoxy groups attached at the terminal and the internal positions of the chain, were essential for structure determination of the products. Peracetyl derivatives of the monomer 1a, dimer 2a, and two stereoisomeric trimers 3a and 4a served as models in the spectrometric characterization and structure determination of the oligomers. The product isolated from the anolyte was amixture of oligomers 5 composed of an average of nine monomer units. The spectrescopic data for the product extracted from the anode 6 suggested that its molecular weight was much higher. In all investigated compounds, the naphtalene rings were proven to be linked at the 1- and 5-positions. The solubility and the spectroscopic data of both oligomers suggested that the chians were not cross-linked. Similar cyclic voltammetric (CV) behavior was found for poly(2,6-dihydroxynaphtalene) films prepared either by the dip-coating technique from a solution of 6 or by the previously reported electrochemical deposition from a solution of 1 by the potential-scanning technique