Design, Synthesis and Property Study of a π-Expanded Naphthalene Diimide-Vinylogous Tetrathiafulvalene Derivative

doi:10.6023/A24060204

Acta Chimica Sinica ›› 2024, Vol. 82 ›› Issue (9): 954-961.DOI: 10.6023/A24060204 Previous Articles Next Articles

Article

核扩展萘二酰亚胺-插烯四硫富瓦烯衍生物的设计合成与性能研究

何萌萌^a^,^b,†, 张瑞^b^,^c,†, 谢玉龙^b^,^c, 葛从伍^b^,^*(), 高希珂^b^,^*()

a 四川师范大学化学与材料科学学院成都 610066
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032
c 中国科学技术大学化学与材料科学学院合肥 230026

投稿日期:2024-06-27 发布日期:2024-07-19
作者简介:
†作者对文章贡献一致
基金资助:
国家自然科学基金(22225506); 中国科学院战略性先导科技专项B类(XDB0520101); 上海市启明星计划(21QA1411100); 中国科学院青年创新促进会(2022252)

Design, Synthesis and Property Study of a π-Expanded Naphthalene Diimide-Vinylogous Tetrathiafulvalene Derivative

Mengmeng He^a^,^b,†, Rui Zhang^b^,^c,†, Yulong Xie^b^,^c, Congwu Ge^b,*(), Xike Gao^b,*()

a College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610066
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
c School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026

Received:2024-06-27 Published:2024-07-19
Contact: *E-mail: gecongwu@sioc.ac.cn,gaoxk@mail.sioc.ac.cn
About author:
†(The authors contributed equally to this work).
Supported by:
National Natural Science Foundation of China(22225506); Strategic Priority Research Program of the Chinese Academy of Sciences(XDB0520101); Shanghai Rising-Star Program(21QA1411100); Youth Innovation Promotion Association CAS(2022252)

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Abstract

Organic field-effect transistors (OFETs) is the basic unit of complementary logic circuit, however, the development of n-type OFETs lags behind of p-type ones due to the barrier of electron injection and the interference from oxygen and water, which hinders the development of complementary logic circuit. Therefore, the design and synthesis of high-performance n-type organic semiconductors and the improvement of device performance and stability have important scientific significance. In this work, a novel naphthalene diimide (NDI)-vinylogous tetrathiafulvalene derivative (BDTNDI-DTYA)₂was designed and synthesized via a π-expanded strategy by fusing the benzene-1,2-dithiol (BDT) and 2-(1,3-dithiol-2-ylidene) acetonitrile (DTYA) moieties onto the NDI core. The chemical structure of the compound was characterized by ¹H NMR, ¹³C NMR, Fourier transform infrared spectroscopy (FT-IR) and high-resolution mass spectrometry (HRMS). The thermal, optical and electrochemical properties of (BDTNDI-DTYA)₂ were characterized by differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), ultraviolet-visible (UV-Vis) absorption spectra and cyclic voltammetry (CV). The energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of (BDTNDI-DTYA)₂ calculated from CV were －5.66 and －4.01 eV, respectively. The edge absorption of (BDTNDI-DTYA)₂ in thin film showed obvious red-shift (68 nm) relative to that in CHCl₃ solution, indicating strong intermolecular interactions in solid state. The bottom-gate and top-contact (BGTC) OFETs based on (BDTNDI-DTYA)₂ fabricated by spin-coating method, showed n-type electron transporting characteristics. The average electron mobility of the untreated devices was 0.04 cm²•V^－1•s^－1 when measured in nitrogen atmosphere and was increased of up to 1.00 cm²•V^－1•s^－1 when the thin films of (BDTNDI-DTYA)₂were thermal annealed at 160 ℃. On the other hand, azulene was used as an additive to treat the thin films of (BDTNDI-DTYA)₂ via sublimation, the average electron mobility of OFETs was increased to 0.98 cm²•V^－1•s^－1. The effect of thermal annealing treatment and azulene-treatment on the performance of (BDTNDI- DTYA)₂-based OFETs were investigated by UV-Vis absorption spectra, atomic force microscopy (AFM) and X-ray dif-fraction (XRD). For UV-Vis absorption spectra of thin films of (BDTNDI-DTYA)₂, after thermal annealing at 160 ℃ and azulene-treatment, the absorption peak in long-wavelength was enhanced and widened relative to that of the untreated thin films with obvious shoulder peaks and red-shifts (35 and 39 nm, respectively). The AFM and XRD results indicated that the improvement of device performance originated from the improved (BDTNDI-DTYA)₂ thin film crystallinity and morphology. In this work, a π-expanded NDI-vinylogous tetrathiafulvalene derivative as n-type organic semiconductor was designed and synthesized, and azulene was used for the first time to effectively regulated the structure and morphology of the active layer of OFETs, which both provide new insights for development of novel organic semiconductors and their high performance OFET devices.

Key words: naphthalene diimide, n-type organic field-effect transistors, electron mobility, structure-performance relationship, additive

Cite this article

Mengmeng He, Rui Zhang, Yulong Xie, Congwu Ge, Xike Gao. Design, Synthesis and Property Study of a π-Expanded Naphthalene Diimide-Vinylogous Tetrathiafulvalene Derivative[J]. Acta Chimica Sinica, 2024, 82(9): 954-961.

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Fig. & Tab. 12

Figure 1. The molecular structures of (a) π-expended naphthalene diimide derivatives; (b) common volatile solid additives; (c) (BDTNDI- DTYA)2

Scheme 1. Synthetic routes of (BDTNDI-DTYA)2

Figure 2. Optimized molecular structure, electron densities of frontier molecular orbitals and frontier molecular orbitals energy levels of the model molecule for compound (BDTNDI-DTYA)2 obtained by DFT calculation

Compound	λ_max/nm		Eopt g^b/eV	E_LUMO^c/eV	E_HOMO^c/eV	ECV g^d/eV
Compound	Sol.^a	Film	Eopt g^b/eV	E_LUMO^c/eV	E_HOMO^c/eV	ECV g^d/eV
(BDTNDI-DTYA)₂	628	696	1.53	－4.01	－5.66	1.65

Table 1. Optical and electrochemical data of (BDTNDI-DTYA)2

Figure 3. UV-Vis absorption spectra of (BDTNDI-DTYA)2 in chloroform solution and in thin film

Figure 4. CV curves of (BDTNDI-DTYA)2 in dichloromethane. 0.1 mol?L－1 Bu4NPF6 as supporting electrolyte, SCE as reference electrode, scan rate of 100 mV?s－1

Compound	Treatment				I_on/I_off^a
(BDTNDI-DTYA)₂	Thermal annealing	As-spun	0.04 (0.05)	16 (11)	10⁵~10⁶
		120 ℃	0.76 (0.80)	19 (16)	10⁵~10⁷
		160 ℃	1.00 (1.42)	14 (8)	10⁶~10⁷
		180 ℃	0.72 (1.04)	13 (8)	10⁵~10⁶
		Azulene	0.98 (1.20)	19 (13)	10⁶~10⁷

Table 2. Characteristics of OFET devices based on (BDTNDI-DTYA)2

Figure 5. The fabrication process of OFETs based on (BDTNDI- DTYA)2

Figure 6. (a) Transfer curves and (b) output curves of OFETs based on (BDTNDI-DTYA)2 treated by azulene

Figure 7. UV-Vis absorption spectra of (BDTNDI-DTYA)2 thin films treated by thermal annealing and azulene

Figure 8. XRD curves of (BDTNDI-DTYA)2 thin films treated by thermal annealing and azulene

Figure 9. AFM images of (BDTNDI-DTYA)2 thin films treated by (a) thermal annealing at 160 ℃ and (b) azulene

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核扩展萘二酰亚胺-插烯四硫富瓦烯衍生物的设计合成与性能研究

Design, Synthesis and Property Study of a π-Expanded Naphthalene Diimide-Vinylogous Tetrathiafulvalene Derivative

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