Synthesis of thiazole-condensed germoles with enhanced electron-deficient properties
Synthesis of thiazole-condensed germoles with enhanced electron-deficient properties
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DOI：
10.1016/j.dyepig.2022.110333
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发表时间：
2022-04
影响因子：
4.5
通讯作者：
Weipeng Sun;Yohei Adachi;J. Ohshita
中科院分区：
文献类型：
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作者：
Weipeng Sun;Yohei Adachi;J. Ohshita
通过噻唑类锂化合物与二氯二辛基锗烷反应，合成了噻唑缩单、双锗烷衍生物（DTzG和GIDTz）。化合物的结构经1H NMR、13 C NMR和质谱确证。溴化GIDTz的单晶结构显示了具有分子间π-π堆积的稠环系统的高平面性。DTzG和GIDTz衍生物的光学和电化学性质表明，该衍生物具有增强的缺电子相比，基于噻吩的germole同类物先前报道。这是支持的密度泛函理论计算，揭示了较低的HOMO和LUMO的噻唑凝聚的germole比噻吩凝聚的同系物。
New thiazole-condensed single and double germole derivatives (DTzG and GIDTz) were prepared by the reactions of respective lithiated thiazole compounds with dichlorodioctylgermane. The compound structures were verified by1H NMR,13C NMR, and mass spectral measurements. The single-crystal structure of brominated GIDTz shows high planarity of the fused ring system with intermolecular π-π stacking. The optical and electrochemical properties of DTzG and GIDTz derivatives indicate that the derivatives possess enhanced electron deficiency compared with thiophene-based germole congeners reported previously. This is supported by density functional theory calculations that reveal lower-lying HOMO and LUMO for the thiazole-condensed germoles than the thiophene-condensed congener.