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

doi:10.6023/cjoc202105023

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (11): 4400-4408.DOI: 10.6023/cjoc202105023 Previous Articles Next Articles

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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

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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Abstract

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

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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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Fig. & Tab. 9

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

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

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

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

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

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

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 ℃

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 ℃

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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