Department of Chemistry, School of Science, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Department of Mechanical Engineering, School of Engineering, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan.
J Org Chem. 2017 Aug 18;82(16):8676-8685. doi: 10.1021/acs.joc.7b01732. Epub 2017 Jul 31.
C o-quinodimethane bisadducts [C(QM)] are promising electron acceptors for bulk heterojuction (BHJ) organic solar cells (OSCs). However, previous production of C(QM) often resulted in excessive regioisomers, which were difficult to purify and might consequently obscure the structure-performance study of the organofullerene acceptors. Herein, the electrosynthesis of C(QM) is reported. The reaction exhibits a strong regiocontrol with generation of fewer regioisomers. Pure regioisomers of cis-2, trans-3, and e C(QM) are obtained, and the structures are solved with single-crystal X-ray diffraction. Interestingly, the cis-2 and trans-3 regioisomers exhibit better photovoltaic performance than the e regioisomer in the OSCs based on poly(3-hexylthiophene) (P3HT), which can be correlated with their structural difference.
并五苯双加成物（C(QM)）是用于体异质结（BHJ）有机太阳能电池（OSC）的有前途的电子受体。然而，以前 C(QM)的生产通常会导致过量的区域异构体，这些异构体难以纯化，可能会掩盖对有机富勒烯受体的结构-性能研究。本文报道了 C(QM)的电合成。该反应表现出强烈的区域控制，生成的区域异构体较少。获得了纯的顺式-2、反式-3 和 e-C(QM)区域异构体，并通过单晶 X 射线衍射确定了它们的结构。有趣的是，在基于聚（3-己基噻吩）（P3HT）的 OSC 中，顺式-2 和反式-3 区域异构体比 e 区域异构体表现出更好的光伏性能，这可以与其结构差异相关联。
