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Improved synthesis of tetraaryl-1,4-dihydropyrrolo[3,2-b]pyrroles a promising dye for organic electronic devices: An experimental and theoretical approach
Dyes and Pigments ( IF 4.1 ) Pub Date : 2017-09-01 , DOI: 10.1016/j.dyepig.2017.08.056
Lucas Michelão Martins , Samuel de Faria Vieira , Gabriel Baldo Baldacim , Bruna Andressa Bregadiolli , José Cláudio Caraschi , Augusto Batagin-Neto , Luiz Carlos da Silva-Filho

Pyrrolo-[3,2-b]pyrroles represent a class of promising materials for application in organic electronics with interesting optoelectronic properties and great synthesis versatility, but yields obtained from varied synthetic routes are still very low, hindering their effective application for industrial purposes. In this report, we present a method for the synthesis of tetraaryl-1,4-dihydropyrrolo-[3,2-b]pyrrole derivatives by multicomponent reactions employing niobium pentachloride as a catalyst. The optical characterization of the products is also presented. Electronic structure calculations were performed to help the interpretation of the synthesis process, as well as the optical properties of the systems. Excellent yields and low reaction times were obtained, indicating that NbCl5 is an efficient catalyst for such systems. The products show promising properties for optoelectronic applications that can be adjusted by the choice of benzaldehyde derivatives used in the synthesis.



中文翻译:

改进的四芳基-1,4-二氢吡咯并[3,2- b ]吡咯的合成方法是有机电子设备的有前途的染料:一种实验和理论方法

吡咯并[3,2- b ]吡咯代表了一类有前途的材料,可用于有机电子领域,具有令人感兴趣的光电子性能和巨大的合成多功能性,但是从各种合成途径获得的收率仍然很低,从而阻碍了它们在工业上的有效应用。在这份报告中,我们提出了一种通过使用五氯化铌作为催化剂的多组分反应合成四芳基-1,4-二氢吡咯并-[3,2- b ]吡咯衍生物的方法。还介绍了产品的光学特性。进行电子结构计算以帮助解释合成过程以及系统的光学性质。获得了极好的收率和低的反应时间,表明NbCl图5是这种系统的有效催化剂。该产品在光电子应用中显示出令人鼓舞的性能,可以通过选择合成中使用的苯甲醛衍生物进行调节。

更新日期:2017-09-01
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