Zhong Xiaowei, Liu Shubin, You Wei
Department of Applied Physical Sciences, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599, USA.
Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599, USA.
Sci Adv. 2024 Aug 23;10(34):eadp8150. doi: 10.1126/sciadv.adp8150. Epub 2024 Aug 21.
Fused-ring electronic acceptors (FREAs) have transformed the field of organic solar cells. However, the prevailing syntheses of FREAs suffer from low yield, difficulty in separation, and high cost. Here, we report new and streamlined syntheses with three distinctive key steps. First, a universal approach to fuse neighboring aromatic units via a single carbon atom is demonstrated with ytterbium triflate and boron trifluoride as the catalysts. This approach allows the incorporation of diverse side-chain combinations. Second, nitrogen atom fusing neighboring aromatics is realized by using oxo-molybdenum catalyst, featuring lower reaction temperatures and enhanced yields. Third, an organic catalyst, proline, is identified to catalyze the aldol condensation with high yield to afford the most typical FREAs having acceptor-donor-acceptor (ADA) configurations. Our new chemistries enable easy syntheses of a wide range of FREAs, substantially expanding the scope and availability of these coveted materials at reduced synthetic cost, particularly for organic electronics.
稠环电子受体（FREAs）已经改变了有机太阳能电池领域。然而，目前FREAs的合成存在产率低、分离困难和成本高的问题。在此，我们报告了具有三个独特关键步骤的新的简化合成方法。首先，以三氟甲磺酸镱和三氟化硼为催化剂，展示了一种通过单个碳原子稠合相邻芳族单元的通用方法。这种方法允许引入多种侧链组合。其次，通过使用氧代钼催化剂实现了相邻芳族化合物的氮原子稠合，其特点是反应温度较低且产率提高。第三，确定了一种有机催化剂脯氨酸，以高产率催化羟醛缩合反应，得到具有受体-供体-受体（ADA）构型的最典型FREAs。我们的新化学方法能够轻松合成多种FREAs，以降低的合成成本大幅扩大了这些令人垂涎的材料的范围和可用性，特别是对于有机电子学领域。
