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

Che En Tsai, Ruo Han Yu, Fang Ju Lin, Yu Ying Lai, Jhih Yang Hsu, Sheng Wen Cheng, Chain-Shu Hsu*, Yen-Ju Cheng

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)5121-5130
Number of pages10
JournalChemistry of Materials
Volume28
Issue number14
DOIs
StatePublished - 26 Jul 2016

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