含硼非苯稠环芳烃★

doi:10.6023/A25050149

化学学报 ›› 2025, Vol. 83 ›› Issue (8): 937-946.DOI: 10.6023/A25050149 上一篇下一篇

综述

含硼非苯稠环芳烃^★

袁刘忠^†, 孙文婷^†, 窦传冬^*()

吉林大学化学学院超分子结构与材料全国重点实验室长春 130012

投稿日期:2025-05-09 发布日期:2025-06-18
通讯作者: 窦传冬

作者简介:

袁刘忠, 2020年本科毕业于重庆师范大学, 然后进入吉林大学化学学院超分子结构与材料全国重点实验室攻读博士研究生.目前主要围绕杂化纳米分子碳及其光电功能开展研究工作.

孙文婷, 2020年本科毕业于曲阜师范大学, 然后进入吉林大学化学学院超分子结构与材料全国重点实验室攻读博士研究生. 目前主要从事含硼有机超分子光电功能材料研究.

窦传冬, 2011年博士毕业于吉林大学, 现为吉林大学化学学院超分子结构与材料全国重点实验室教授, 博士生导师. 围绕含硼有机功能材料为研究主题, 专心于含硼共轭分子和高分子的合成化学与功能调控研究, 推动形成了“含硼功能分子碳”特色方向.

^★ “中国青年化学家”专辑.

基金资助:
国家自然科学基金(52373182); 国家自然科学基金(22175074)

Boron-Containing Nonbenzenoid Polycyclic Aromatic Hydrocarbons^★

Liuzhong Yuan, Wenting Sun, Chuandong Dou^*()

State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012

Received:2025-05-09 Published:2025-06-18
Contact: Chuandong Dou
About author:
†These authors contributed equally to this work
^★ For the VSI “Rising Stars in Chemistry”.
Supported by:
National Natural Science Foundation of China(52373182); National Natural Science Foundation of China(22175074)

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摘要/Abstract

含硼非苯稠环芳烃是一类结合了硼原子和非苯基元的共轭多环芳烃体系, 其展现出与经典碳基稠环芳烃明显不同的电子结构和物化性质, 被广泛应用于有机发光二极管、有机场效应晶体管等器件技术领域. 近年来, 通过引入大位阻基团或采用结构约束的设计策略提升硼原子稳定性, 以及采用高效可控的有机合成方法, 已发展出一系列新颖的含硼非苯稠环芳烃, 包括硼氮型、硼氧型、硼硫型、以及纯硼掺杂的非苯稠环芳烃. 这些分子不仅具有优美的拓扑结构和良好的稳定性, 还展现出独特的光电性质和优良器件性能. 此外, 它们还具有路易斯酸性, 能够与路易斯碱配位形成路易斯酸碱加合物, 进而表现出刺激响应功能. 尽管该领域取得了诸多进展, 但仍然缺乏含硼非苯稠环芳烃研究进展的系统总结. 在这篇综述中, 旨在重点介绍含硼非苯稠环芳烃的设计与合成策略, 概述其独特的物理性质和功能特性, 并对含硼非苯稠环芳烃面临的合成挑战与未来发展方向进行了分析和展望.

关键词: 硼, 非苯稠环芳烃, 合成方法, 拓扑结构, 光电功能

Doping heteroatoms (B, N, O, S, P) into polycyclic aromatic hydrocarbons (PAHs) has been developed as an efficient strategy to achieve intriguing electronic structures and optoelectronic properties. In particular, boron-containing nonbenzenoid PAHs are a class of conjugated polycyclic π systems that combine the boron atoms and nonbenzenoid motifs, such as pentagon and heptagon rings. These molecules not only possess wonderful topological structures, but also have electronic structures and physicochemical properties that are obviously different from those of traditional carbon-based PAHs. Owing to these characteristics, they have exhibited great potential applications in optoelectronic devices, including organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs). However, the high reactivity and sensitivity of boron atoms to moisture and oxygen leads to severe limitations in design and synthetic methods, and difficulty in construction of boron-containing π-systems. Thus, following the design strategies for enhancing the stability of the boron atom by introducing bulky substituents or utilizing structural constraint and the efficient synthetic approaches, a series of boron-containing nonbenzenoid PAHs, including boron/nitrogen-type, boron/oxygen-type, boron/sulfur-type and pristine boron-doped systems, have been dramatically developed. These molecules not only possess intriguing topological structures and excellent stability, but also exhibit fascinating optoelectronic properties, such as thermally activated delayed fluorescence, reversible redox capabilities and magnetic properties. Moreover, they exhibit sufficient Lewis acidity, enabling them to coordinate with Lewis bases to form Lewis acid-base adducts, thus achieving stimuli-responsive functions. Therefore, the precise introduction of boron atoms into polycyclic structures to construct boron-containing nonbenzenoid PAH systems and fine modulation of physical properties and functions has become the key topic in the research fields of PAHs, organoborane chemistry and organic functional materials. In this review, we aim to highlight the design and synthetic strategies of boron-containing nonbenzenoid PAHs, along with their intriguing electronic structures, physical properties and practical applications. Additionally, the synthesis challenges and future development opportunities of these molecules are analyzed and prospected.

Key words: boron, nonbenzenoid polycyclic aromatic hydrocarbons, synthetic method, topological structure, optoelectronic function

引用此文

袁刘忠, 孙文婷, 窦传冬. 含硼非苯稠环芳烃^★[J]. 化学学报, 2025, 83(8): 937-946.

Liuzhong Yuan, Wenting Sun, Chuandong Dou. Boron-Containing Nonbenzenoid Polycyclic Aromatic Hydrocarbons^★[J]. Acta Chimica Sinica, 2025, 83(8): 937-946.

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图/表 8

图1. 含硼非苯稠环芳烃的设计策略

Figure 1. Schematic illustration for the design of boron-containing nonbenzenoid polycyclic aromatic hydrocarbons

图2. 硼氮共杂非苯稠环芳烃5、6、8、10和12的合成路线

Figure 2. Synthetic routes of B/N co-doped nonbenzenoid PAHs 5, 6, 8, 10 and 12

图3. (a)硼氮共杂非苯稠环芳烃14及其硼酯15b的合成路线和四例多重共振分子14~19的化学结构; (b)发射峰为550至650 nm的TADF-OLED的EQEmax总结[84]; (c)甲苯中14和19的紫外吸收和荧光光谱; (d)甲苯中19的瞬态衰减曲线[89]

Figure 3. (a) Synthetic route of B/N co-doped nonbenzenoid PAHs 14 and 15b, and chemical structures of B/N co-doped nonbenzenoid PAHs 14~19; (b) EQEmax summary of TADF-OLEDs with an emission peak from 550 to 650 nm[84], Copyright 2021 Royal Society of Chemistry; (c) UV/Vis absorption and fluorescence spectra of 14 and 19 in toluene; (d) Transient PL decay curves of 19 in toluene solution[89]. Copyright 2024 WILEY-VCH

图4. (a, b)硼氮共杂非苯稠环芳烃21、22和25的合成路线; (c, d)甲苯中21和22的紫外吸收光谱、荧光光谱、圆二色谱图和圆偏振发光光谱图[90]; (e)全碳和B/X掺杂茚并芴的双自由基指数和单-三线态能隙[91]

Figure 4. (a, b) Synthetic routes of B/N co-doped nonbenzenoid PAHs 21, 22 and 25; (c) UV/Vis absorption and fluorescence spectra, (d) CD and CPL spectra of 21 and 22[90]; (e) Diradical characters and singlet-triplet energy gaps of s-indacene-based all-carbon and B/X-doped heterocyclic PAHs[91]. Copyright 2023, 2024 WILEY-VCH

图5. (a)硼氧共杂非苯稠环芳烃27、28和31的合成路线、以及29的化学结构; (b)不同浓度的29在激光照射下的温度变化[94]; (c) 29在经历5个激光开关循环后的加热与冷却曲线[94]; (d) 31的超导量子干涉仪测试图[95]; (e)四氢呋喃中31的荧光光谱图[95]

Figure 5. (a) Synthetic routes of B/O co-doped nonbenzenoid PAHs 27, 28 and 31, and chemical structure of 29; (b) Temperature variations of various concentrations of 29 under laser irradiation[94]; (c) The heating and cooling curves of 29 upon 5 cycles of laser on and off[94]; (d) The SQUID measurements of the powder 31[95]; (e) Fluorescence spectra of 31[95]. Copyright 2021, 2023 Royal Society of Chemistry

图6. (a)硼硫共杂非苯稠环芳烃33、35和37的合成路线; (b) 35的紫外吸收/荧光光谱[97]

图7. (a)硼杂非苯稠环芳烃39、41、42、44、45、48和51的合成路线; (b) 45的光致解离机理[101]; (c) 51-α向51-γ转换的机制[104]

Figure 7. (a) Synthetic routes of B-doped nonbenzenoid PAHs 39, 41, 42, 44, 45, 48 and 51; (b) A plausible energy diagram for the photodissociation of 45[101]; (c) Estimated transformation mechanism from 51-α to 51-γ[104]. Copyright 2014, 2024 American Chemical Society

图8. (a)硼杂非苯稠环芳烃54、55、58、59和60的合成路线; (b) 59的单晶结构; (c)氯仿中59与甲基磺酸滴定过程的紫外吸收光谱图[106]

Figure 8. (a) Synthetic routes of B-doped nonbenzenoid PAHs 54, 55, 58, 59 and 60; (b) Single crystal structure of 59; (c) Absorption spectra for titration of 59 in CHCl3 with CH3SO3H[106]. Copyright 2024 WILEY-VCH.

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含硼非苯稠环芳烃^★

Boron-Containing Nonbenzenoid Polycyclic Aromatic Hydrocarbons^★

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含硼非苯稠环芳烃★

Boron-Containing Nonbenzenoid Polycyclic Aromatic Hydrocarbons★

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含硼非苯稠环芳烃^★

Boron-Containing Nonbenzenoid Polycyclic Aromatic Hydrocarbons^★