Research progress in “bottom-up” chemical synthesis of nanographenes

doi:10.11949/0438-1157.20200043

Abstract

Abstract:

Nanographene is a part of graphene structure, and its size is generally in the range of 1—100 nm. It can be used as a structural unit to construct functional carbon materials such as graphene, carbon nanotubes and fullerene. Due to the quantum-size effect, edge effect and interface effect, nanographenes are of potential for molecular electronics and the sensors. Herein, we will discuss the bottom-up chemical synthesis for nanographenes, including graphene molecules with seven- or eight-membered rings, heteroatom-doped nanographenes and edge functionalization of nanographenes. The advantages of different synthetic methods and their limitations are highlighed. The properties and applications of nanographenes with different structures have been summarized. The trends and key issues to be tackled in future are also briefly outlined.

Key words: bottom-up synthesis, nanographene, heteroatom-doped, edge functionalization, chemical synthesis

摘要：

纳米石墨烯是组成石墨烯结构的一部分，尺寸一般介于1~100 nm，可以作为结构单元构筑石墨烯、碳纳米管和富勒烯等功能碳材料。纳米石墨烯具有一定的量子效应、边缘效应和界面效应，在新型分子电子器件、传感器等领域有着巨大的应用潜力。本文重点介绍“自下而上”化学合成纳米石墨烯的方法、含七元环或八元环特殊结构的纳米石墨烯、杂原子掺杂的纳米石墨烯以及纳米石墨烯的边缘修饰。探讨了不同合成方法的优势和特点，介绍了不同结构纳米石墨烯的性能及应用前景，概括了“自下而上”合成纳米石墨烯存在的问题及未来的发展趋势。

关键词: 自下而上合成, 纳米石墨烯, 杂原子掺杂, 边缘修饰, 化学合成

CLC Number:

TB 34

Yating ZHANG, Bochao ZHANG, Jianlan ZHANG, Keke LI, Yongqiang DANG, Yingfeng DUAN. Research progress in “bottom-up” chemical synthesis of nanographenes[J]. CIESC Journal, 2020, 71(6): 2628-2642.

张亚婷, 张博超, 张建兰, 李可可, 党永强, 段瑛峰. “自下而上”化学合成纳米石墨烯的研究进展[J]. 化工学报, 2020, 71(6): 2628-2642.

Figures/Tables 24

Fig.1 Schematic illustration of graphene terminology defined according to their size scale [14]

Fig.2 Synthesis of HBC by Clar’s method

Fig.3 Synthesis of HBC from hexaphenylbenzene precursor

Fig.4 Synthesis of HBC precursor by Suzuki-Miyaura coupling reaction

Fig.5 Synthesis of nanographenes by [4+2] cycloaddition of aryne

Fig.6 Synthesis of nanographenes by [2+2+2] cycloaddition of aryne

Fig.7 Synthesis of nanographenes by Yamamoto coupling reaction

Fig.8 Synthesis of hexabenzobenzene derivatives by photocatalysis

Fig.9 [n]Circulenes with different central rings

Fig.10 Nanographenes with an embeded seven-membered ring

Fig.11 Nanographenes with five seven-membered rings

Fig.12 Nanographenes with eight-membered rings

Fig.13 Nanographenes with pyrrole rings

Fig.14 Other N-doped nanographenes

Fig.15 Nanographenes with thiophene ring

Fig.16 S-doped nanographenes with different structures

Fig.17 HBC derivatives substituted by halogen

Fig.18 Edge functionalization of nanographenes

Fig.19 Edge chlorination of nanographenes

Fig.20 Borylation of nanographenes and their further transformation

Fig.21 Schematic diagram of HBC amphiphile (a), self-assembled double-layered belt (b) and graphite nanotubes (c) [76]

Fig.22 Application of three-dimensional nanographenes containing three HBC structures in cellular fluorescence imaging [77]

Fig.23 Schematic diagram of structure of NGHC (a) and diffusion of lithium ions and electrons during discharge and charging of NGHCs electrodes (b) [81]

Fig.24 Ti/Pd ID electrode sensor prepared by using CNT and HBC solution [83]

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