End-Capping Groups for Small-Molecule Organic Semiconducting Materials: Synthetic Investigation and Photovoltaic Applications through Direct C-H (Hetero)arylation

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• 作者：Te-Jui Lu ; Po-Han Lin ; Kun-Mu Lee and Ching-Yuan Liu
• 刊名：European Journal of Organic Chemistry
• 出版年：2017
• 出版时间：January 3, 2017
• 年：2017
• 卷：2017
• 期：1
• 页码：111-123
• 全文大小：2372K
• ISSN：1099-0690

文摘

A Pd-catalyzed C–H (hetero)arylation methodology has been optimized for the efficient synthesis of various useful end-capping groups that are widely applied in small-molecule optoelectronic materials. We report herein the synthesis of a broad scope of target molecules ranging from donor-type through acceptor-type to hybrid-type end-capping groups. To demonstrate their application in dye-sensitized solar cells, we have designed two new D–A–π–A′-type organic sensitizers (CYL-3 and CYL-4), which were synthesized in a step-economic manner by sequential C–H arylations using the facilely obtained end-capping groups. The devices based on CYL-3 and CYL-4 give V_oc values of 0.67–0.71 V, J_sc values of 10.07–11.63 mA cm^–2, and FF values of 70.6–72.9 %, which correspond to overall power conversion efficiencies of 4.76–6.02 %. This work is expected to become a practical synthetic alternative allowing materials scientists to access small-molecule organic materials in fewer synthetic transformations.