萘二酰亚胺手性衍生物的合成及其场效应晶体管性能研究

doi:10.6023/cjoc202105023

有机化学 ›› 2021, Vol. 41 ›› Issue (11): 4400-4408.DOI: 10.6023/cjoc202105023 上一篇下一篇

研究论文

萘二酰亚胺手性衍生物的合成及其场效应晶体管性能研究

周敏^a^,^b, 李晶^b, 程杰^b, 葛从伍^b^,^*(), 程探宇^a^,^*(), 高希珂^b^,^*()

a 上海师范大学化学与材料科学学院上海 200234
b 中国科学院上海有机化学研究所中国科学院有机功能分子合成与组装化学重点实验室上海 200032

收稿日期:2021-05-12 修回日期:2021-07-15 发布日期:2021-08-17
通讯作者: 葛从伍, 程探宇, 高希珂
基金资助:
国家自然科学基金(21522209); 国家自然科学基金(21790362); 上海市科学技术委员会(19XD1424700); 上海市科学技术委员会(18JC1410600)

Synthesis and Field-Effect Characteristics of the Chiral Naphthalene Diimide Derivatives

Min Zhou^a^,^b, Jing Li^b, Jie Cheng^b, Congwu Ge^b(), Tanyu Cheng^a(), Xike Gao^b()

a College of Chemistry and Materials Science, Shanghai Normal University, Shanghai 200234
b Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032

Received:2021-05-12 Revised:2021-07-15 Published:2021-08-17
Contact: Congwu Ge, Tanyu Cheng, Xike Gao
Supported by:
National Natural Science Foundation of China(21522209); National Natural Science Foundation of China(21790362); Science and Technology Commission of Shanghai Municipality(19XD1424700); Science and Technology Commission of Shanghai Municipality(18JC1410600)

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1. 0253-2786-41-11-4400辅助材料.pdf(25850KB)

摘要/Abstract

萘二酰亚胺类共轭分子是一类经典且被广泛研究的有机半导体材料. 在本工作中, 通过亲芳核取代反应将手性环己二胺引入萘二酰亚胺的两端合成了光学纯化合物(I-R, I-S), 内消旋化合物(I-R,S), 以及经I-R和I-S等物质的量共混得到的外消旋混合物(I-rac), 并对这些化合物的紫外-可见吸收光谱、圆二色谱及电化学性质进行了研究. 光学纯(I-R, I-S)和消旋体(I-R,S, I-rac)材料在溶液状态下的光谱吸收完全一致, 但其薄膜吸收存在差异, 消旋体薄膜的最大吸收峰较光学纯材料红移了约5 nm, 这表明它们的聚集态结构有所不同. 以这些化合物或混合物为活性层制备的有机场效应晶体管(OFET)在氮气条件下均表现出p型半导体特征. 其中, 内消旋体(I-R,S)和外消旋体(I-rac) OFET器件的空穴迁移率分别为0.074和0.075 cm²•V^–1•s^–1, 均高于光学纯材料I-R和I-S的器件性能(空穴迁移率约为0.04 cm²•V^–1•s^–1). 研究结果表明, 手性诱导分子组装产生不同的聚集态结构, 从而对材料的器件性能产生一定影响, 这为萘二酰亚胺类有机功能分子的发展提供了新思路.

关键词: 萘二酰亚胺, 手性, 聚集态结构, 有机场效应晶体管

Naphthalene diimides (NDI)-based conjugated molecules were a class of typical and widely studied organic semiconducting materials. The optically pure compounds (I-R and I-S) and mesomer (I-R,S) by S_NAr reactions between tetraboromo-NDI and 1,2-diaminocyclohexane were designed and synthesized, moreover, the racemic mixture (I-rac) was obtained by mixing I-R and I-S equimolarly. The UV-vis absorption spectroscopy, cyclic voltammetry, and circular dichroism of four materials were studied. The UV-Vis absorptions in solution were consistent, while the absorptions in film were slightly different between the optically pure compounds and the mesomer or raceme, indicating the different aggregate structures. Accordingly, the organic field-effect transistors (OFET) by using these materials as the active layer were prepared. They all exhibited p-type organic semiconducting characteristics under nitrogen conditions. Meanwhile, mesomer (I-R,S) and raceme (I-rac) showed better OFET device performance (hole mobility: about 0.075 cm²•V^–1•s^–1) than that of the optically pure compounds I-R and I-S (hole mobility: about 0.04 cm²•V^–1•s^–1). The atomic force microscopy (AFM) studies demonstrated that thin films of mesomer (I-R,S) and raceme (I-rac) annealed at 100 ℃ showed larger form size of microstructures with fewer grain boundaries, which was consistent with the enhanced device performance after thermal annealing. This paper proved that the chirality influenced the molecule self-assembly, packing structure and the resulting device performance.

Key words: naphthalene diimides, chirality, aggregate structure, organic field-effect transistors

引用此文

周敏, 李晶, 程杰, 葛从伍, 程探宇, 高希珂. 萘二酰亚胺手性衍生物的合成及其场效应晶体管性能研究[J]. 有机化学, 2021, 41(11): 4400-4408.

Min Zhou, Jing Li, Jie Cheng, Congwu Ge, Tanyu Cheng, Xike Gao. Synthesis and Field-Effect Characteristics of the Chiral Naphthalene Diimide Derivatives[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4400-4408.

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图/表 9

图式1. 化合物I-R, I-S和I-R,S的合成路线

Scheme 1. Synthetic routes of compounds I-R, I-S and I-R,S

Compd.	λ_max/nm		E_g^a/eV	T_d^b/℃	T_pt^c/℃
Compd.	Solid	Film	E_g^a/eV	T_d^b/℃	Heating/Cooling
I-R	630	639	1.78	416	277/283
I-S	630	639	1.78	416	277/283
I-R,S	630	644	1.78	418	277/287
I-rac	630	644	1.78	424	285/292

表1. I-R, I-S, I-R,S和I-rac的光谱和热力学数据

Table 1. Optical and electrochemical data for I-R, I-S, I-R,S and I-rac

图1. I-R的单晶结构图

Figure 1. Crystal structure of I-R (a) Top view, (b) side view, and (c) molecular packing

图2. I-R, I-S, I-R,S和I-rac的紫外-可见吸收光谱

Figure 2. UV-Vis absorption spectra of I-R, I-S, I-R,S and I-rac (a) In dichloromethane solution, (b) as-spun thin films

图3. I-R, I-S, I-R,S和I-rac在二氯甲烷溶液中的(a)圆偏振吸收光谱和(b)循环伏安曲线

Figure 3. (a) CD spectra and (b) cyclic voltammogram of I-R, I-S, I-R,S and I-rac in dichloromethane solution 0.1 mol/L $\text{Bu}_{\text{4}}^{}\text{NPF}_{6}^{}$ as the electrolyte, SCE as reference electrode, scan rate of 100 mV/s

Compd.	Annealing temperature/℃	µ_h,max/ (cm²•V^–1•s^–1)	V_T/V	I_On/I_Off
I-R	As-spun	3.2×10^–5	6.1	10²~10³
	100	4.0×10^–2	–62.9	10⁴~10⁵
	180	4.6×10^–3	–40.4	10³~10⁴
I-S	As-spun	3.8×10^–5	1.8	10²~10³
	100	3.6×10^–2	–62.4	10⁴~10⁵
	180	4.6×10^–3	–42.6	10³~10⁴
I-R,S	As-spun	4.9×10^–5	2.9	10²~10³
	100	7.4×10^–2	–50.6	10⁴~10⁵
	180	1.4×10^–2	–40.0	10⁴~10⁵
I-rac	As-spun	1.7×10^–5	3.0	10²~10³
	100	7.5×10^–2	–62.5	10⁴~10⁵
	180	1.5×10^–2	–37.0	10⁴~10⁵

表2. I-R, I-S, I-R,S和I-rac的OFET器件性能

Table 2. Characteristics of OFET devices based on I-R, I-S, I-R,S and I-rac

图4. 基于材料I-R (a, e), I-S (b, f), I-R,S (c, g)和I-rac (d, h)的OFET器件在100 ℃退火条件下的转移和输出曲线

Figure 4. Typical transfer and output curves of OFET devices based on I-R (a, e), I-S (b, f), I-R,S (c, g) and I-rac (d, h) annealed at 100 ℃

图5. I-R, I-S, I-R,S和I-rac的薄膜的XRD衍射图谱

Figure 5. XRD patterns of the films of I-R, I-S, I-R,S and I-rac (a) as-spun, (b) annealed at 100 ℃

图6. I-R (a, e), I-S (b, f), I-R,S (c, g)和I-rac (d, h)薄膜在未退火(a, b, c, d)和100 ℃热退火(e, f, g, h)条件下的AFM图

Figure 6. AFM height images of as-spun thin films of (a) I-R, (b) I-S, (c) I-R,S and (d) I-rac, and AFM height images of thin films of (e) I-R, (f) I-S, (g) I-R,S and (h) I-rac annealed at 100 ℃

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萘二酰亚胺手性衍生物的合成及其场效应晶体管性能研究

Synthesis and Field-Effect Characteristics of the Chiral Naphthalene Diimide Derivatives

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