The development of an efficient synthetic protocol for multiply bay-functionalized perylenes and application of these products to photovoltaics are reported. Tetrabenzyl 1-(4-tert-butylphenoxy)perylene-3,4,9,10-tetracarboxylate underwent a regioselective bromination at the 7-position followed by a further bromination at the 12-position to provide a 7,12-dibromide in high 84% yield. This compound was transformed into a tetrasubstituted C2h -symmetric dibromide by a controlled monoetherification and a final bromination. The synthetic versatility of the new brominated precursors was demonstrated by their application to cross-coupling reactions, cyanation, and derivatization to the corresponding perylene diimide (PDI). Owing to the high solubility and the raised LUMO level, the obtained tetrasubstituted PDI showed significant advantages as an acceptor material for photovoltaic applications, exhibiting a remarkably high open-circuit voltage (VOC ) reaching 1.00 V. The observed high VOC could be understood by reduction of energy offset for charge separation and non-radiative recombination loss.

中文翻译：

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Per的区域选择性海湾官能化向有机光伏受体材料的定制合成。

据报道，已开发出一种有效的合成方案，用于多种海湾官能化的per，并将这些产品应用于光伏。1-（4-叔丁基苯氧基）per四苄基-3,4,9,10-四羧酸酯在7位进行区域选择性溴化，然后在12位进行进一步溴化，以提供高浓度的7,12-二溴化物产率84％。通过受控的单醚化和最终的溴化，将该化合物转化为四取代的C 2h-对称的二溴化物。通过将新溴化前体用于交叉偶联反应，氰化和衍生化为相应的per二酰亚胺（PDI），证明了它们的合成多功能性。由于高溶解度和提高的LUMO水平，