A Multi-Substituted Pyrenyl Carbon Nanohoop: Synthesis, Photophysical and Charge Transport Properties

doi:10.6023/cjoc202507016

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (2): 539-544.DOI: 10.6023/cjoc202507016 Previous Articles Next Articles

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多取代芘基碳纳米环的合成、表征和电荷传输性质

李科, 方鹏炜, 张新宇, 韦康, 袁冰, 杜平武^*()

中国科学技术大学材料科学与工程系精准智能化学全国重点实验室合肥 230026

收稿日期:2025-07-13 修回日期:2025-10-05 发布日期:2025-10-29
通讯作者: 杜平武
基金资助:
国家自然科学基金(22225108); 国家自然科学基金(223B2120)

A Multi-Substituted Pyrenyl Carbon Nanohoop: Synthesis, Photophysical and Charge Transport Properties

Ke Li, Pengwei Fang, Xinyu Zhang, Kang Wei, Bing Yuan, Pingwu Du^*()

Key Laboratory of Precision and Intelligent Chemistry, Department of Materials Science and Engineering, University of Science and Technology of China, Hefei 230026

Received:2025-07-13 Revised:2025-10-05 Published:2025-10-29
Contact: Pingwu Du
Supported by:
National Natural Science Foundation of China(22225108); National Natural Science Foundation of China(223B2120)

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Abstract

The longitudinal π-extension of carbon nanohoops is one of the most effective bottom-up synthetic strategies toward carbon nanotubes (CNTs). Herein, the precise synthesis of a multi-substituted carbon nanohoop ([12]CPP-8PBPy) based on cycloparaphenylenes (CPPs) grafted with eight pyrene-functionalized units was reported. This structurally well-defined nanohoop not only acts as a segment of armchair-type CNTs but also achieves enhanced longitudinal π-extension. The structure of [12]CPP-8PBPy was confirmed by high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR). The photophysical properties were studied by UV/Vis and photoluminescence spectroscopy. The potential applications of [12]CPP-8PBPy in electron-transport devices were further investigated.

Key words: pyrene derivatives, π-extension, conjugated macrocycle, charge transport

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Ke Li, Pengwei Fang, Xinyu Zhang, Kang Wei, Bing Yuan, Pingwu Du. A Multi-Substituted Pyrenyl Carbon Nanohoop: Synthesis, Photophysical and Charge Transport Properties[J]. Chinese Journal of Organic Chemistry, 2026, 46(2): 539-544.

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Fig. & Tab. 5

Figure 1. Design of the tubular [12]CPP-8PBPy carbon nanohoop as the finite segment of SWCNTs

Figure 2. Synthestic procedure of [12]CPP-8PBPy

Figure 3. (a) The MALDI-TOF spectrum and simulated data for [12]CPP-8PBPy. (b) The aromatic regions of the 1H NMR spectra of [12]CPP-8PBPy. (c) Expanded 2D 1H-1H ROESY NMR spectrum of [12]CPP-8PBPy. (d) Expanded 2D 1H-1H COSY NMR spectrum of [12]CPP-8PBPy

Figure 4. (a) UV/Vis absorption (solid lines) and fluorescence spectra (dashed lines) of [12]CPP-8PBPy in CH2Cl2 (1.0×10－5 M) at room temperature; (b) Emission lifetime of [12]CPP- 8PBPy in CH2Cl2

Figure 5. (a) Schematic diagram of the BG/BC OFET structures. (b) Transfer characteristics of BG/BC FET devices based on [12]CPP-8PBPy. The channel length and width of the device are 50 μm and 5 mm, respectively

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多取代芘基碳纳米环的合成、表征和电荷传输性质

A Multi-Substituted Pyrenyl Carbon Nanohoop: Synthesis, Photophysical and Charge Transport Properties

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References 42

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