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The Tetraarylpyrrolo[3,2-b]pyrroles—From Serendipitous Discovery to Promising Heterocyclic Optoelectronic Materials
Accounts of Chemical Research ( IF 18.3 ) Pub Date : 2017-08-10 00:00:00 , DOI: 10.1021/acs.accounts.7b00275
Maciej Krzeszewski 1 , Dorota Gryko 1 , Daniel T. Gryko 1
Affiliation  

Progress in organic optoelectronics requires compounds possessing a suitable combination of photophysical and electronic properties. Another key constraint encompasses the availability of feasible, and hopefully scalable, synthetic procedures for preparing the molecular scaffolds of interest. A multicomponent reaction of aromatic aldehydes, aromatic amines, and butane-2,3-dione that was discovered in 2013 gives straightforward access to previously unavailable 1,2,4,5-tetraarylpyrrolo[3,2-b]pyrroles. These dyes are examples of heteropentalenes—a class of 10-π-electron aromatic compounds. The unsurpassed variety of aromatic aldehydes and primary aromatic amines, which are commercially available or easy to prepare, allows for potential routes to thousands of 1,2,4,5-tetraarylpyrrolo[3,2-b]pyrroles that are currently unknown. This synthetic procedure offers a means for preparing the pyrrolopyroles in gram quantities and isolating them by simple filtration.

中文翻译:

四芳基吡咯并[3,2- b ]吡咯—从偶然发现到有希望的杂环光电材料

有机光电子学的进步要求化合物具有光物理和电子性质的适当组合。另一个关键约束条件包括用于制备目标分子支架的可行且有望可扩展的合成程序的可用性。2013年发现的芳族醛,芳族胺和2,3-丁烷的多组分反应可直接获得先前无法获得的1,2,4,5-四芳基吡咯并[3,2- b ]吡咯。这些染料是杂戊烯(一类10-π电子芳族化合物)的实例。商业上可获得或易于制备的芳香醛和伯芳香胺种类繁多,为潜在的途径提供了成千上万的1,2,4,5-四芳基吡咯并[3,2- b]吡咯,目前未知。该合成方法提供了制备克量的吡咯并吡咯并通过简单过滤将其分离的方法。
更新日期:2017-08-10
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