Decafluorinated and Perfluorinated Warped Nanographenes: Synthesis, Structural Analysis, and PropertiesClick to copy article linkArticle link copied!
- Xue-Peng ZhangXue-Peng ZhangState Key Laboratory for Physical Chemistry of Solid Surfaces, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), Department of Chemistry, Xiamen University, Xiamen 361005, ChinaMore by Xue-Peng Zhang
- Si-Wei YingSi-Wei YingState Key Laboratory for Physical Chemistry of Solid Surfaces, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), Department of Chemistry, Xiamen University, Xiamen 361005, ChinaMore by Si-Wei Ying
- Yi-Lu ZhangYi-Lu ZhangState Key Laboratory for Physical Chemistry of Solid Surfaces, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), Department of Chemistry, Xiamen University, Xiamen 361005, ChinaMore by Yi-Lu Zhang
- Wen-Xin ZhangWen-Xin ZhangState Key Laboratory for Physical Chemistry of Solid Surfaces, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), Department of Chemistry, Xiamen University, Xiamen 361005, ChinaMore by Wen-Xin Zhang
- Wenjie ShiWenjie ShiState Key Laboratory for Physical Chemistry of Solid Surfaces, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), Department of Chemistry, Xiamen University, Xiamen 361005, ChinaMore by Wenjie Shi
- Bin-Wen ChenBin-Wen ChenState Key Laboratory for Physical Chemistry of Solid Surfaces, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), Department of Chemistry, Xiamen University, Xiamen 361005, ChinaMore by Bin-Wen Chen
- Han-Rui TianHan-Rui TianState Key Laboratory for Physical Chemistry of Solid Surfaces, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), Department of Chemistry, Xiamen University, Xiamen 361005, ChinaMore by Han-Rui Tian
- Gan XuGan XuState Key Laboratory for Physical Chemistry of Solid Surfaces, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), Department of Chemistry, Xiamen University, Xiamen 361005, ChinaMore by Gan Xu
- Shan-Shan WangShan-Shan WangState Key Laboratory for Physical Chemistry of Solid Surfaces, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), Department of Chemistry, Xiamen University, Xiamen 361005, ChinaMore by Shan-Shan Wang
- Qianyan Zhang*Qianyan Zhang*Email: [email protected]State Key Laboratory for Physical Chemistry of Solid Surfaces, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), Department of Chemistry, Xiamen University, Xiamen 361005, ChinaMore by Qianyan Zhang
- Su-Yuan XieSu-Yuan XieState Key Laboratory for Physical Chemistry of Solid Surfaces, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), Department of Chemistry, Xiamen University, Xiamen 361005, ChinaMore by Su-Yuan Xie
- Lan-Sun ZhengLan-Sun ZhengState Key Laboratory for Physical Chemistry of Solid Surfaces, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), Department of Chemistry, Xiamen University, Xiamen 361005, ChinaMore by Lan-Sun Zheng
Abstract
Fluorination is a useful approach for tailoring the physicochemical properties of nanocarbon materials. However, owing to the violent reactivity of fluorination, achieving edge-perfluorination of nanographene while maintaining its original π-conjugated structure is challenging. Instead of using traditional fluorination, here, we employed a bottom-up strategy involving fluorine preinstallation and synthesized decafluorinated and perfluorinated warped nanographenes (DFWNG and PFWNG, respectively) through a 10-fold Suzuki–Miyaura coupling followed by a harsh Scholl reaction, whereby precisely edge-perfluorinated nanographene with an intact π-conjugated structure was achieved for the first time. X-ray crystallography confirmed the intact π-conjugated structure and more twisted saddle-shaped geometry of PFWNG compared to that of DFWNG. Dynamic study revealed that the 26-ring carbon framework of PFWNG is less flexible than that of DFWNG and the pristine WNG, enabling chirality resolution of PFWNG and facilitating the achievement of CD spectra at −10 °C. The edge-perfluorination of PFWNG resulted in improved solubility, lower lowest unoccupied molecular orbital, and a surface electrostatic potentials/dipole moment direction opposite those of the pristine WNG. Likely owing to its intact π-conjugated structure, PFWNG exhibits comparable electron mobility with well-known PC61BM. Furthermore, perfluorination improves thermal stability and hydrophobicity, making PFWNG suitable for use as a thermostable/hydrophobic n-type semiconductor material. In the future, this fluorination strategy can be used to synthesize other perfluorinated nanocarbon materials, such as perfluorinated graphene nanoribbons and porous nanocarbon.
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