Azulene-Substituted Donor-Acceptor Polymethines and 1,6’-Bi-, 1,6′;3,6′′-Ter-, and Quinqueazulenes via Zincke Salts: Synthesis, and Structural, Optical, and Electrochemical Properties,ChemPlusChem

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Azulene-Substituted Donor-Acceptor Polymethines and 1,6’-Bi-, 1,6′;3,6′′-Ter-, and Quinqueazulenes via Zincke Salts: Synthesis, and Structural, Optical, and Electrochemical Properties
ChemPlusChem ( IF 3.0 ) Pub Date : 2021-04-27 , DOI: 10.1002/cplu.202100174
Taku Shoji _{1,

2} , Akari Yamazaki ₁ , Yukino Ariga ₁ , Mayumi Uda ₁ , Daichi Ando ₂ , Nichika Sasahara ₂ , Naohito Kai ₃ , Shunji Ito ₃

Affiliation

Azulene-substituted donor-acceptor polymethines, bi-, ter-, and quinqueazulenes composed of the 1,6′-biazulene unit have been successfully prepared from corresponding Zincke salts. The synthesis of polymethines through the reaction of Zincke salts with several amines, followed by a Knoevenagel reaction with malononitrile, was accomplished in moderate to high yields (40–92 %). Meanwhile, the reaction of Zincke salts with secondary amines and the subsequent sequential condensation-cyclization with cyclopentadienide ions, so-called Ziegler-Hafner method, produced the corresponding 1,6′-biazulenes, 1,6′;3,6′′-terazulenes, and quinqueazulene, respectively. The structural, optical, and electrochemical properties of the azulene-substituted donor-acceptor polymethines, bi-, ter-, and quinqueazulenes were revealed by single-crystal X-ray structure analysis, UV/vis spectroscopy, voltammetry analysis, spectroelectrochemistry, and theoretical calculations. These results suggested that the substituents on the azulene ring and their substitution positions directly affect their reactivities, optical and electrochemical properties.

中文翻译：

通过锌盐取代甘菊环的供体-受体聚次甲基和 1,6'-Bi-、1,6';3,6''-Ter- 和喹蓝烯：合成以及结构、光学和电化学性质

由1,6'-联苯菊烯单元组成的薁取代的供体-受体聚次甲基、双、三、和喹甘菊烯已由相应的锌盐成功制备。通过锌盐与几种胺的反应，然后与丙二腈进行克诺文格尔反应，合成了聚次甲基，以中等到高产率（40-92%）完成。同时，锌盐与仲胺的反应以及随后与环戊二烯化物离子的连续缩合环化，即所谓的齐格勒-哈夫纳法，产生了相应的1,6'-联薁烯，1,6';3,6''-分别是四萁烯和喹萁烯。通过单晶 X 射线结构分析、紫外/可见光谱、伏安分析、光谱电化学和理论揭示了薁取代的供体-受体聚次甲基、双、三和喹甘菊烯的结构、光学和电化学性质。计算。这些结果表明甘菊环上的取代基及其取代位置直接影响其反应活性、光学和电化学性能。

更新日期：2021-06-28

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