Methods for the synthesis of pyrrolo[3,2-b]pyrroles containing hexaphenylbenzene moieties at the 2- and 5-positions or the 1- and 4-positions have been developed. It was shown that placing a hexaphenylbenzene moiety at the 2- and 5-positions requires a Diels–Alder reaction between an alkyne-substituted pyrrolopyrrole core and a 2,3,4,5-tetraphenylcyclopenta-2,4-dien-1-one. The resulting dyes show a strong blue fluorescence that was hypsochromically shifted by chlorination at the 3- and 6-positions. The overall conjugation between the hexaphenylbenzene moieties and the pyrrolopyrrole core is limited, as evident from their photophysical properties. The hexaphenylbenzene moieties attached to the pyrrolo[3,2-b]pyrrole core could not be transformed into hexa-peri-hexabenzocoronenes through intramolecular oxidative aromatic coupling.

中文翻译：

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六苯基苯-吡咯并[3,2-b]吡咯的合成及光物理性质

已经开发了合成在 2- 和 5- 位或 1- 和 4- 位含有六苯基苯部分的吡咯并[3,2-b] 吡咯的方法。结果表明，将六苯基苯部分置于 2-和 5-位需要炔烃取代的吡咯并吡咯核与 2,3,4,5-四苯基环戊-2,4-dien-1-one 之间的 Diels-Alder 反应. 所得染料显示出强烈的蓝色荧光，该荧光在 3 位和 6 位被氯化发生了色差转移。六苯基苯部分和吡咯并吡咯核之间的整体共轭是有限的，这从它们的光物理特性中可以看出。连接到吡咯并[3,2-b]吡咯核的六苯基苯部分不能通过分子内氧化芳香偶联转化为六邻六苯并芴酮。