Synthesis of a 4,9-Didodecyl Angular-Shaped Naphthodiselenophene Building Block To Achieve High-Mobility Transistors

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• 作者：Che-En Tsai ; Ruo-Han Yu ; Fang-Ju Lin ; Yu-Ying Lai ; Jhih-Yang Hsu ; Sheng-Wen Cheng ; Chain-Shu Hsu ; Yen-Ju Cheng
• 刊名：Chemistry of Materials
• 出版年：2016
• 出版时间：July 26, 2016
• 年：2016
• 卷：28
• 期：14
• 页码：5121-5130
• 全文大小：613K
• 年卷期：0
• ISSN：1520-5002

文摘

A new tetracyclic 4,9-dialkyl angular-shaped naphthodiselenophene (4,9-α-aNDS) was designed and synthesized. The naphthalene core in 4,9-α-aNDS is formed by the DBU-induced 6π-cyclization of an (E)-1,2-bis(3-(tetradec-1-yn-1-yl)selenophen-2-yl)ethene intermediate followed by the second PtCl₂-catalyzed benzannulation. This synthetic protocol allows for incorporating two dodecyl groups regiospecifically at 4,9-positions of the resulting α-aNDS. An ordered supramolecular self-assembly formed via noncovalent selenium–selenium interactions with a short contact of 3.5 Å was observed in the single-crystal structure of 4,9-α-aNDS. The distannylated α-aNDS building block was copolymerized with Br-DTFBT and Br-DPP acceptors by Stille cross coupling to form two new donor–acceptor polymers PαNDSDTFBT and PαNDSDPP, respectively. The bottom-gate/top-contact organic field-effect devices using the PαNDSDTFBT and PαNDSDPP semiconductors accomplished superior hole mobility of 3.77 and 2.17 cm² V^–1 s^–1, respectively, which are among the highest mobilities reported to date.