石墨炔衍生物的合成与应用

doi:10.3866/PKU.WHXB202206029

物理化学学报 >> 2023, Vol. 39 >> Issue (1): 2206029.doi: 10.3866/PKU.WHXB202206029

石墨炔衍生物的合成与应用

李晓慧¹^,³, 李晓东², 孙全虎⁴^,⁵, 何建江⁴, 杨泽⁴, 肖金冲¹^,*(), 黄长水²^,⁴^,*()

¹ 河北大学化学与环境科学学院, 河北省化学生物学重点实验室, 河北保定 071002
² 中国科学院化学研究所, 北京 100190
³ 河北农业大学理学院, 河北保定 071001
⁴ 中国科学院青岛生物能源与过程研究所, 山东青岛 266101
⁵ 中国科学院大学, 北京 100049

收稿日期:2022-06-20 录用日期:2022-07-22 发布日期:2022-08-08
通讯作者: 肖金冲,黄长水 E-mail:jcxiaoicas@163.com;huangcs@iccas.ac.cn
基金资助:
河北省自然科学基金重点项目(B2021201043);国家自然科学基金(21701182);国家自然科学基金(21790050);国家自然科学基金(21790051);国家自然科学基金(11704024);中国科学院前沿科学重点研究计划(QYZDB-SSW-JSC052)

Synthesis and Applications of Graphdiyne Derivatives

Xiaohui Li¹^,³, Xiaodong Li², Quanhu Sun⁴^,⁵, Jianjiang He⁴, Ze Yang⁴, Jinchong Xiao¹^,*(), Changshui Huang²^,⁴^,*()

¹ College of Chemistry and Environmental Science, Key Laboratory of Chemical Biology of Hebei Province, Hebei University, Baoding 071002, Hebei Province, China
² Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
³ College of Science, Hebei Agricultural University, Baoding 071001, Hebei Province, China
⁴ Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, Shandong Province, China
⁵ University of Chinese Academy of Sciences, Beijing 100190, China

Received:2022-06-20 Accepted:2022-07-22 Published:2022-08-08
Contact: Jinchong Xiao,Changshui Huang E-mail:jcxiaoicas@163.com;huangcs@iccas.ac.cn
About author:Email: huangcs@iccas.ac.cn (C.H.)
Email: jcxiaoicas@163.com (J.X.)
Supported by:
the Key Project of the Natural Science Foundation of Hebei Province(B2021201043);the National Natural Science Foundation of China(21701182);the National Natural Science Foundation of China(21790050);the National Natural Science Foundation of China(21790051);the National Natural Science Foundation of China(11704024);the Frontier Science Research Project of the Chinese Academy of Sciences(QYZDB-SSW-JSC052)

摘要/Abstract

摘要：

石墨炔是由sp和sp²两种杂化碳构成的新型二维碳同素异形体。基于石墨炔化学合成规律和独特优势，利用其他芳炔前体替代六乙炔基苯，可以获得结构特异、尺寸可控的石墨炔基衍生物，而局域碳骨架的改变可以实现石墨炔衍生物性能调控，包括电导率、带隙、迁移率、空腔尺寸和电荷分离等。这类具有优良半导体性能的石墨炔基衍生物可以广泛应用于电化学储能、电催化、光电转换器件、非线性光学等诸多领域。本文主要综述了近年来石墨炔衍生物的优化设计、结构表征和光电性能，并对其代表性应用进行了总结和展望。

关键词: 石墨炔衍生物, 电化学储能, 电催化, 光电, 非线性光学

Abstract:

Graphdiyne (GDY) bearing sp- and sp²-hybridized carbon networks, which is usually artificially synthesized via the in situ homocoupling reaction of hexaethylbenzene on copper foil, is an emerging two-dimensional (2D) carbon allotrope. During preparation, well-defined GDY structures including nanowires, nanowalls, and nanotubes are obtained. Such materials with varying morphologies have been shown to possess promising electronic, chemical, magnetic, and mechanical properties, rendering them applicable in various domains including energy storage, catalysis, and field emission. In addition, replacing hexaethylbenzene with other aryne derivatives under similar synthesis conditions has resulted in the generation of various GDY derivatives. Thus, a series of GDY derivatives with specific structures and controllable sizes have been readily prepared in recent years. Aryne precursors typically contain polycyclic aromatic carbocycles, heteroarenes (e.g., N, B, S, P, Si, Ge, and Ga). The intrinsic GDY has also been doped with metal elements (e.g., Hg, Ag, and Au). Chemical synthetic strategies such as Glaser coupling, Glaser-Hay coupling, and Eglinton coupling are also described. The structural design of various precursors has been effectively tailored to the constitution of the local carbon framework of GDY-based materials, which has enabled the realization of the targeted performance in terms of the electronic conductivity, band gap, mobility, cavity size, and charge separation. For example, three-dimensional (3D) carbyne riched nanospheres formed by the extended coupling of spatially rigid-structured spirobifluorene have provided abundant storage spaces and convenient multi-directional transmission paths for metal ions. The use of hetero-doped GDY has enabled the effective optimization of the thermal stability and mechanical, electronic, and optical properties. Metal element-based GDY, referred to as "metalated" GDY, could serve as efficient bifunctional catalysts possessing favorable transport properties to facilitate the diffusion of small molecules. By extension, such materials can be used more broadly in electrochemical energy storage, electrocatalysis, optoelectronics, nonlinear optics, oil-water separation, and numerous other fields. In this review, we have summarized the design, synthesis, and structural characterization of various GDY derivatives through the recently demonstrated substitution of various aryne precursors for hexaethylbenzene, while examining the functional relationships between the desired optoelectronic properties of GDY derivatives and their defined nanostructures and morphologies. In addition, important prospective applications of GDY derivatives have been described. These observations may motivate the construction of novel polar and electron-rich GDY derivatives with unique properties that can address practical challenges encountered in various devices.

Key words: Graphdiyne derivative, Electrochemical energy storage, Electrocatalysis, Optoelectronics, Nonlinear optics

李晓慧, 李晓东, 孙全虎, 何建江, 杨泽, 肖金冲, 黄长水. 石墨炔衍生物的合成与应用[J]. 物理化学学报, 2023, 39(1), 2206029. doi: 10.3866/PKU.WHXB202206029

Xiaohui Li, Xiaodong Li, Quanhu Sun, Jianjiang He, Ze Yang, Jinchong Xiao, Changshui Huang. Synthesis and Applications of Graphdiyne Derivatives[J]. Acta Phys. -Chim. Sin. 2023, 39(1), 2206029. doi: 10.3866/PKU.WHXB202206029

链接本文: https://www.whxb.pku.edu.cn/CN/10.3866/PKU.WHXB202206029

https://www.whxb.pku.edu.cn/CN/Y2023/V39/I1/2206029

图/表 16

图1

图2

图3

表1

石墨炔及其衍生物结构、制备方法、应用与性能一览表1, 2, 36, 43, 49-56, 58, 60, 62"

Number	Sample	Precursor	Structure	Preparation	Application	Performance
1	GDY ^{1, 2}			Glaser coupling	Energy conversion and storage, optoelectronic devices, catalysis, etc. ^3–29	LIBs: With a reversible capacity of 552 mAh?g^?1 at a current density of 50 mA?g^?1 after performing 200 cycles
2	TZ-GDY ⁵⁶			Glaser coupling (copper substrate)	–	–
3	Ben-GDY ³⁶			Glaser coupling (copper substrate)	–	–
4	TPE-GDY ^{49, 50}			Glaser coupling (copper substrate)	Nonlinear optics (NLO)	Show clear chirality in the ultraviolet band and exhibit a good nonlinear frequency doubling response
5	TTF-GDY ⁵¹			Glaser coupling (without substrate)	Electrode materials of LIBs	With a reversible capacity of 837.6 mAh?g^?1
6	SBFCY-NS ⁵²			Glaser coupling (without substrate)	Electrode materials of LIBs, and SIBs	LIBs: With a capacity of 1050 mAh?g^?1 at a current density of 50 mA?g^?1; SIBs: With a capacity of 130 mAh?g^?1 at a current density of 5 A g^?1 after 3000 circles
7	BBT-GDY ⁴³			Glaser-Hay coupling (copper substrate)	–	Show semiconductor characteristics with a bandgap of 2.38 eV, and conductivity of 2 × 10^?3 S·m^?1 (r.t.)
8	CoPor-GDY ⁵⁴			Glaser-Hay coupling (copper substrate)	–	The overpotential of HER was 308 mV at 10 mA?cm^?2 and the Tafel slope was 68 mV?dec^?1; the overpotential of OER was 400 mV at 10 mA?cm^?2 and the Tafel slope was 129 mV?dec^?1.
9	PQ-GDY ⁵³			Glaser-Hay coupling (copper substrate)	Electrode materials of LIBs	With a reversible capacity of 570.0 mAh?g^?1 after performing 800 cycles at a current density of 200 mA?g^?1
10	TP-GDY ⁵⁵			Glaser-Hay coupling (without substrate)	–	After modification: freestanding morphology, smooth texture, domain size > 1 mm, thickness 220 nm
11	COP-GY ⁶²			Sonogashira coupling (melamine sponge or cotton fabric substrate, etc.)	Conductive and superhydrophobic materials for oil-water separation, biosensing, etc.	Cotton fabrics with COP-GY showed oil-water separation efficiency of 95.5%; COP-GY in melamine sponge showed superhydrophobicity with a contact angle of 154°.
12	Ag-TET ⁶⁰			Glaser coupling (Ag substrate)	–	–
13	HgL1 ⁵⁸			Glaser coupling (glass slide, silicon wafer or quartz substrate)	Passively Q-switched (PQS)	With stable and perfect broadband nonlinear saturable absorption (SA) properties at both 532 and 1064 nm
14	HgL2 ⁵⁸			Glaser coupling (glass slide, silicon wafer or quartz substrate)	Passively Q-switched (PQS)	With stable and perfect broadband nonlinear saturable absorption (SA) properties at both 532 and 1064 nm

表1

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石墨炔衍生物的合成与应用

Synthesis and Applications of Graphdiyne Derivatives

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