| 研究課題/領域番号 |
17K14478
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| 研究機関 | 国立研究開発法人理化学研究所 |
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研究代表者 |
WANG CHENGYUAN 国立研究開発法人理化学研究所, 創発物性科学研究センター, 特別研究員 (20772932)
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| 研究期間 (年度) |
2017-04-01 – 2019-03-31
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| キーワード | Alkylthionation / Thienoacenes / Packing / Molecular Orientation / OFETs |
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| 研究実績の概要 |
Based on my preliminary results and the proposed research plan, firstly, a straightforward chemistry to introduce alkylthio groups at the β-position of thienoacenes has been successfully developed. This chemistry utilizes disulfur dichloride as electrophilic reagent for cyclizaiton, which is reported firstly by this study.
Secondly, the model study of methylthionation of benzo[1,2-b:4,5-b’]dithiophene (BDT) to selectively tune the packing, molecular orientation and semiconducting properties has been completed. β-position methylthionation of BDT can change the packing of molecules into the rubrene-like "pitched" π-stacking and realize "edge-on" molecular orientation on the substrate. With these features β-methylthionated BDT shows more promising performance in single-crystal OFETs than its α-counterparts. This study suggests novel molecular designing strategy to develop high performance semiconducting materials.
Thirdly, thiacycle rings are used to modify BDT with S atoms at different positions and various ring size. This work emphasizes the importance of the position of S atoms in thiacycle rings and ring size in the functionalization of thienoacenes to tune their semiconducting properties.
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| 現在までの達成度 (区分) |
現在までの達成度 (区分)
2: おおむね順調に進展している
理由
Based on the research plan, I have achieved the two specific aims proposed in fiscal year 2017.
For the specific aim 1, the chemistry of β-position alkylthionation of thienoacenes can be applicable to various alkylthio groups. This chemistry gives moderate yield with mild conditions, with which we can successfully synthesize a series of target β-alkylthionated thienoacenes.
For the specific aim 2, the target four compounds can be successfully synthesized. The single crystals of the four molecules can be obtained, thus we can study the packing of the molecules. Through the thin-film transistor performance of the molecules, we can demonstrate how the crystal engineering to affect the semiconducting properties of molecules.
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| 今後の研究の推進方策 |
Based on the proposed research plan and my current research progress, in fiscal year 2018 I will focus on specific aim 3, which is the alkylthionation of larger π-conjugated thienoacenes, i.e., naphthodithiophenes(NDTs) and anthradithiophenes (ADTs).
The chemistry developed in fiscal year 2017 will be used to modify NDTs and ADTs. Alkylthio groups will be introduced to different positions i.e., α- and β-positions. Single crystals will be prepared to analyze the packing of the alkylthonated thienoacenes. X-ray diffraction measurement will be used to demonstrate the molecular orientation of the molecules on the substrates. Single-crystal based OFETs will be fabricated to investigate the semiconducting properties of the novel molecules.
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| 次年度使用額が生じた理由 |
In this fiscal year I will be focused on the specific aim 3, which is study of NDTs and ADTs. The starting materials to synthesize NDTs and ADTs are very expensive. In addition, I will purchase software to carry out theoretical calculation of transfer integrals of the crystals. These theoretical and experimental studies require more funding support. Thus, I need to transfer some money to this fiscal year to conduct the project, in order to make sure the project can be completed smoothly.
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