An efficient synthesis of hydrolytically and thermally stable 4,8-dibromobenzo[1,2-d:4,5-d’]bis([1,2,3]thiadiazole) by the bromination of its parent heterocycle is reported. The structure of 4,8-dibromobenzo[1,2-d:4,5-d’]bis([1,2,3]thiadiazole) was confirmed by X-ray analysis. The conditions for the selective aromatic nucleophilic substitution of one bromine atom in this heterocyclic system by nitrogen nucleophiles are found, whereas thiols formed the bis-derivatives only. Suzuki–Miyaura cross-coupling reactions were found to be an effective method for the selective formation of various mono- and di(het)arylated derivatives of strong electron-deficient benzo[1,2-d:4,5-d’]bis([1,2,3]thiadiazole), and Stille coupling can be employed for the preparation of bis-arylated heterocycles, which can be considered as useful building blocks for the synthesis of DSSCs and OLEDs components.

中文翻译：

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强缺电子苯并[1,2-d:4,5-d']双([1,2,3]噻二唑)的4,8-二溴衍生物的高效合成及其SNAr和交叉偶联反应

报道了通过溴化其母体杂环有效合成水解和热稳定的 4,8-二溴苯并[1,2- d :4,5 - d ']双([1,2,3]噻二唑)。4,8-二溴苯并[1,2- d :4,5- d']bis([1,2,3]thiadiazole) 通过 X 射线分析得到证实。发现了通过氮亲核试剂在该杂环体系中选择性芳族亲核取代一个溴原子的条件，而硫醇仅形成双衍生物。铃木-宫浦交叉偶联反应被发现是选择性形成强缺电子苯并 [1,2-d:4,5-d']bis 的各种单（杂）芳基化衍生物的有效方法([1,2,3]thiadiazole) 和 Stille 偶联可用于制备双芳基化杂环，可将其视为合成 DSSC 和 OLED 组件的有用构建单元。