手性共轭有机三芳基硼(Ar3B)发光材料研究进展

doi:10.6023/cjoc202407002

摘要/Abstract

手性π-共轭材料通常展现出优异的光物理性质以及稳定的手性特性, 在有机光电材料领域具有广泛的应用. 由于三芳基硼(Ar₃B)独特的电子特性将三芳基硼骨架嵌入到手性π-共轭体系中, 使其体系展现出优异的手性光学特性, 形成手性共轭有机三芳基硼材料, 在化学和材料科学领域均引起广泛关注. 首先介绍了手性共轭有机三芳基硼材料领域的基本概念. 接着, 根据手性来源, 分别从轴手性、螺旋手性、面手性以及中心手性讨论了手性共轭三芳基硼材料的合成策略、结构特性, 并深入探讨了这些材料在吸收、发射、荧光量子效率等手性光电性质和应用方面的最新进展, 这些特性对于手性有机光电器件的性能至关重要. 最后, 对当前研究中的挑战和未来发展趋势进行了展望, 合理预期了手性共轭有机三芳基硼材料的发展潜力和应用前景.

关键词: 三芳基硼, 手性, 圆偏振发光

The chiral π-conjugated materials typically exhibit excellent photophysical properties and stable chiral chara- cteristics, which have a wide range of applications in the field of organic optoelectronic materials. Due to the unique electronic properties of triarylboron (Ar₃B), incorporating this framework into chiral π-conjugated systems results in systems with superior chiroptical properties, forming chiral conjugated organic triarylboron materials, and has attracted widespread attention in both chemistry and materials science. This review first introduces the basic concepts in the field of chiral conjugated organic triarylboron materials. Then, the synthetic strategies, structural characteristics of chiral conjugated triarylboron materials based on the source of chirality, including axial chirality, helical chirality, planar chirality, and central chirality are discussed. It also delves into the latest advances in these materials absorption spectrum, emission spectrum, fluorescence quantum efficiency, and other chiroptical optoelectronic properties, which are crucial for the performance of chiral organic optoelectronic devices. Finally, the current challenges and future development trends of chiral conjugated organic triarylboron materials are discussed, and the potential application of this material is reasonably anticipated.

Key words: triarylboron, chirality, circularly polarized luminescence

引用此文

李艳秋, 贾亚薇, 陈磅宽. 手性共轭有机三芳基硼(Ar₃B)发光材料研究进展[J]. 有机化学, 2025, 45(4): 1119-1136.

Yanqiu Li, Yawei Jia, Pangkuan Chen. Recent Progress of Chiral Conjugated Organic Triarylboron (Ar₃B) Luminescent Materials[J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1119-1136.

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图/表 25

图式1. 三芳基硼有机化合物的常用合成方法小结

Scheme 1. A summary of common synthesis methods for triarylborane organic compounds

图1. 三芳基硼化合物的结构示意图; (a, b) Bsp2中心的p-π共轭, 以及(c)三取代硼中心(Bsp2)的亲核攻击

Figure 1. Schematic presentation of triarylboranes; (a,b) p-π conjugation of Bsp2 centres, and (c) nucleophilic attack of trisubstituted boron atom (Bsp2)

图2. (a) 1-1和1-2的结构; (b) 1-1和1-2在环己烷中的紫外/可见吸收光谱和荧光光谱; (c) 1-2在四氢呋喃中(1.23×10－4 mol/L, λex=320 nm)进行F－滴定加入TBAF (20 equiv.), CPL(顶部)和荧光(底部)光谱的变化[39]

Figure 2. (a) Structures of 1-1 and 1-2; (b) UV/Vis absorption and fluorescence spectra of 1-1 and 1-2 in cyclohexane; (c) CPL (top) and fluorescence (bottom) spectral changes of 1-2 (1.23×10－4 mol/L, λex=320 nm) in THF upon addition of F－ as the tetrabutylammonium fluoride (TBAF) salt (20 equiv.) Reproduced with permission.[39] Copyright 2019, Wiley-VCH GmbH, Weinheim.

Compound	λ_abs/nm	λ_em/nm	Φ_PL/%	ǀg_lumǀ(×10^－3)
1-2	396^a	472	58	1.53
2-2	332^b	445	15	0.36
3-2	358^b	436	81	1.30
4-2	—	459	91	—

表1. 轴手性分子的光物理性质

Table 1. Photophysical properties of axially chiral molecules

图3. (a) 2-1、2-2和2-3的结构; (b) MeBTT, 2-1, p-BTT, 2-2, m-BTT和2-3在二氯甲烷中的吸光光谱和发射光谱(c=1.0×10－5 mol/L, λex=λabs,max)(插图: 照片显示了在365 nm紫外光照射下二氯甲烷中溶液的发射颜色); (c) 298 K氮气氛围下2-3在不同极性的溶剂中(c=1.0×10－5 mol/L)的CPL图谱[40]

Figure 3. (a) Structures of 2-1 and 2-2; (b) Absorption and emission spectra of MeBTT, 2-1, p-BTT, 2-2, m-BTT and 2-3 in CH2Cl2 (c=1.0×10－5 mol/L under N2, λex=λabs,max)(Inset: Photographs showing their emission colours of solutions in CH2Cl2 under 365 nm UV irradiation); (c) CPL spectra of enantiomers for 2-3 after optical resolution in solvents (c=1.0×10－5 mol/L) of different polarities under N2 at 298 K. Reproduced with permission.[40] Copyright 2022, the Royal Society of Chemistry.

图4. (a) 3-1和3-2的结构; (b, c) 298 K氮气氛围下手性大环化合物的对映体在二氯甲烷中(c=1.0×10－5 mol/L)的CD光谱[41]

Figure 4. (a) Structures of 3-1 and 3-2; (b, c) CD spectra of enantiomers of chiral macrocycles in CH2Cl2 (c=1.0×10－5 mol/L) under N2 at 298 K Reproduced with permission.[41] Copyright 2023, Wiley-VCH GmbH, Weinheim.

图5. (a) 4-1和4-2的结构; (b) 4-1和4-2的紫外可见吸收和PL光谱; (c)和(d)是R/S-4-1和R/S-4-2的CPEL光谱[42]

Figure 5. (a) Structures of 4-1 and 4-2; (b) UV-Vis absorption and PL spectra of 4-1 and 4-2; (c) and (d) CPEL spectra of R/S-4-1 and R/S-4-2 Reproduced with permission.[42] Copyright 2024, Wiley-VCH GmbH, Weinheim

图6. (a) 5-1、5-2和5-3的结构; (b)三芳基硼[5]螺烯及其母体化合物HC在环己烷中的紫外-可见吸收光谱以及(c)荧光光谱 (λex=350 nm)[45]

Figure 6. (a) Structures of 5-1, 5-2 and 5-3; (b) UV-vis absorption and (c) fluorescence spectra of triarylborane-based [5] helicenes and the parent HC in cyclohexane (λex=350 nm) Reproduced with permission.[45] Copyright 2018, the American Chemical Society

Compound	λ_abs/nm	λ_em/nm	Φ_PL/%	ǀg_lumǀ (×10^－3)
5-1	413^a	443	80	—
6-1	422^b	445	51	6.51
7-2	425^b	452	5	3.56
8-1	319^c	459	21	1.56
9-2	381^a	504	100	4.69
10-1	467^d	500	88	—
11-1	627^a	600	100	33
12-2	505^d	520	85	1.1
13-2	427^d	444	95	1.5
14	592	—	—	1.7
15	546^d	578	98	5.8

表2. 螺旋手性分子的光物理性质

Table 2. Photophysical properties of helical molecules

图7. (a) 6-1和6-2的结构; (b) 6-1和6-2的CD和(c) CPL图[46]

图8. (a) 7-1和7-2的结构; (b) 7-1和7-2的CD光谱(顶部)和紫外-可见吸收光谱(底部); (c) 7-1和7-2的CPL光谱(顶部)和荧光光谱(底部)(环己烷, c=1.0×10－5 mol/L, λex=320 nm)[47]

Figure 8. (a) Structures of 7-1 and 7-2; (b) CD (top) and UV-vis absorption (bottom) spectra of 7-1 and 7-2; (c) CPL (top) and fluorescence (bottom) spectra of 7-1 and 7-2 (cyclohexane, c=1.0×10－5 mol/L, λex=320 nm) Reproduced with permission.[47] Copyright 2021, the American Chemical Society.

图9. (a) 8-1和8-2的结构; (b) 8-1和(c) 8-2的P型和M型对映体在正己烷、四氢呋喃和丙烯腈中的CPL光谱(c=1.0×10－5 mol/L); (d) 8-1和8-2在正己烷中的glum[48]

Figure 9. (a) Structures of 8-1 and 8-2; CPL spectra of the P and M enantiomers for (b) 8-1 and (c) 8-2 in n-hexane, THF and CH3CN (c=1.0×10－5 mol/L); (d) Luminescence dissymmetry factors (glum) of 8-1 and 8-2 in n-hexane Reproduced with permission.[48] Copyright 2022, the Royal Society of Chemistry.

图10. (a) 9-1、9-2和9-3的结构; (b) 9-1、9-2和9-3在二氯甲烷中的吸光光谱和发射光谱(λex=λabs,max, c=1.0×10－5 mol/L)(插图: 在365 nm紫外光照射下的发射照片); (c) 9-1 (c=5×10－5 mol/L, CH2Cl2/CH3CN)在不同量的NOSbF6化学氧化下的紫外-可见-近红外吸收光谱(插图: 在加入NOSbF6后的溶液照片[49])

Figure 10. (a) Structures of 9-1, 9-2 and 9-3; (b) Absorption and emission spectra of 9-1, 9-2 and 9-3 (λex=λabs,max, c=1.0×10－5 mol/L) in CH2Cl2 (inset: emission photographs under 365 nm UV irradiation); (c) Chemical oxidations of 9-1 (c=5×10－5 mol/L, CH2Cl2/ CH3CN) with different amounts of NOSbF6 monitored by UV-vis-NIR absorption spectra (inset: photographs of solutions after the addition of NOSbF6) Reproduced with permission.[49] Copyright 2023, the American Chemical Society.

图11. (a) 10-1和10-2的结构; 甲苯溶液中的10-1 (b、c)和10-2 (d、e) (1×10－5 mol/L, 298 K)的标准化的紫外-可见吸收光谱和荧光光谱、CD光谱以及CPPL随波长变化的曲线(插图: 365nm紫外光下拍摄的甲苯溶液中的样品照片)[50]

Figure 11. (a) Structures of 10-1 and 10-2; Normalized UV-vis absorption and fluorescence spectra, CD spectra and CPPL, versus wavelength curves of 10-1 (b, c respectively) and 10-2 (d, e respectively) in toluene solution (1×10－5 mol/L, 298 K) (inset: photograph under 365 nm UV in toluene) Reproduced with permission.[50] Copyright 2021, Wiley-VCH GmbH, Weinheim.

图12. (a) 11-1、11-2和11-3的结构; (b) 11-1、11-2、11-3在二氯甲烷溶液中(1×10－5 mol/L)的CD光谱以及(c)根据公式(gabs=Δε/ε)计算出的(P,P)构型的相应|gabs|值[51]

Figure 12. (a) Structures of 11-1, 11-2 and 11-3; (b) Circular dichroism spectra of 11-1, 11-2, 11-3 in dichloromethane solution (1× 10－5 mol/L), and (c) the corresponding |gabs| of (P,P)-configuration calculated according to the equation gabs=Δε/ε Reproduced with permission.[51] Copyright 2021, the American Chemical Society.

图13. (a) 12-1和12-2的结构; (b) 12-1 (ee>99%)和(c) 12-2 (ee>99%) (293 K, 除氧甲苯, c≈10－6 mol/L)的CD(实线)和CPL(虚线)光谱[53]

Figure 13. (a) Structures of 12-1 and 12-2. Chiroptical properties (293 K, deoxygenated toluene, c≈10－6 mol/L) CD (solid line) and CPL (dotted line) spectra of (b) 12-1 (ee>99%) and (c) 12-2 (ee>99%) Reproduced with permission.[53] Copyright 2023, Wiley-VCH GmbH, Weinheim.

图14. (a) 13-1和13-2的结构; (b)荧光量子产率ΦPL之间的比较; (c) J-V-L特性图谱; (d)基于对映体器件的CPEL随波长变化曲线[54]

Figure 14. (a) Structures of 13-1 and 13-2; (b) Comparison of photoluminescence quantum yield (ΦPL); (c) Current density and luminance versus voltage (J-V-L) characteristics; (d) Circularly polarized electroluminescence (CPEL) versus wavelength curves of the enantiomer-based devices[54] Reproduced with permission.[54] Copyright 2023, Wiley-VCH GmbH, Weinheim.

图15. (a) 14的结构; (b)三维图表总结了基于全色发射MR-BN发射器的代表性CP-OLEDs的EQE和gEL因子; (c)基于M,M-和P,P-14的CP-OLEDs的对称CPEL光谱; (d)在初始亮度为10000 cd?cm－2的条件下基于M,M-14、P,P-14和Ir(mphmq)2tmd的设备运行寿命[55]

Figure 15. (a) Structure of 14; (b) Three-dimensional diagram summarizing the EQE and gEL factors of the representative CP-OLEDs based on the MR-BN emitters with full-color emission; (c) Symmetrical CPEL spectra of CP-OLEDs based on M,M- and P,P-14; (d) Operational lifetimes of the devices based on M,M-14, P,P-14 and Ir(mphmq)2tmd at an initial luminance of 10000 cd?cm－2 Reproduced with permission.[55] Copyright 2023, Wiley-VCH GmbH, Weinheim.

图16. (a) 15的结构; (b)基于MR-BN螺烯的代表性CP-OLEDs的EQE和gEL值的三维总结图表; (c)基于P-和M-15的CP-OLEDs的CPEL光谱和gEL值; (d) 15在甲苯(1×10－5 mol/L)中的吸光、荧光和磷光光谱[56]

Figure 16. (a) Structure of 15; (b) Three-dimensional diagram summarizing the EQE and gEL value of the representative CP-OLEDs based on MR-BN helicenes; (c) CPEL spectra and gEL values of CP-OLEDs based on P- and M-15; (d) Absorption, fluorescence and phosphorescence spectra of 15 in toluene (1×10－5 mol/L) Reproduced with permission.[56] Copyright 2024, Wiley-VCH GmbH, Weinheim.

图17. (a) 16-1、16-2、16-3和16-4的结构; (b) 16-3 (λex=340 nm)和(c) 16-4 (λex=330 nm)的CD光谱(c=1.0×10－5 mol/L)以及CPL、紫外-可见吸收和荧光光谱(c=1.0×10－5 mol/L)[58]

Figure 17. (a) Structures of 16-1、16-2、16-3 and 16-4; CD (c=5.0×10－5 mol/L) and CPL, UV-vis absorption and fluorescence (c=1.0×10－5 mol/L) spectra of (b) 16-3 (λex=340 nm) and (c) 16-4 (λex=330 nm) Reproduced with permission.[58] Copyright 2021, the American Chemical Society.

Compound	λ_abs/nm	λ_em/nm	Φ_PL/%	ǀg_lumǀ(×10^－3)
16-1	374^a	531	46	4.24
17-1	—	478	98	0.54
18-2	345^b	390	99	4.62
19	553^c	653	7.6	—

表3. 面手性分子的光物理性质

Table 3. Photophysical properties of planar chiral molecules

图18. (a) 17-1和17-2的结构; (b)~(c) (R/S)-17-1和(R/S)-17-2在稀释甲苯中CD和CPL光谱[59]

Figure 18. (a) Structures of 17-1 and 17-2; (b)~(c) Circular dichroism, circularly polarized photoluminescence spectra of (R/S)-17-1 and (R/S)-17-2 in dilute toluene Reproduced with permission.[59] Copyright 2022, Wiley-VCH GmbH, Weinheim.

图19. (a) 18-1和18-2的结构; (b) 18-2的对映体在不同溶剂中的CD和(c) CPL (c=5.0×10?5 mol?L－1, λex=306 nm); (d) rac-18-2的紫外-可见吸收和发射光谱(λex=306 nm)以及PhBB的光谱(λex=345 nm)[实线表示在四氢呋喃溶液中(c=1.0×10－5 mol?L－1)的情况, 虚线表示固态的情况. 插图: 在365 nm紫外光照射下, rac-18-2和PhBB在四氢呋喃中的颜色[60]]

Figure 19. (a) Structures of 18-1 and 18-2; (b) CD and (c) CPL of enantiomers of 18-2 in different solvents (c=5.0×10－5 mol?L－1, λex=306 nm); (d) UV-vis absorption and emission spectra of rac-18-2 (λex=306 nm) and PhBB (λex=345 nm) (solid line, in THF (c= 1.0×10－5 mol?L－1), dashed line and solid state. Inset: photographs showing the emission colors of rac-18-2 and PhBB in THF under 365 nm UV irradiation) Reproduced with permission.[60] Copyright 2023, the Royal Society of Chemistry.

图20. (a) 19-1和19-2的结构; (b) 19-1 (λex=373 nm)和19-2 (λex=373 nm)在正己烷中(c=1.0×10－5 mol/L)的紫外-可见吸收和发射光谱(插图: 365纳米紫外光下的发射照片); 在PMMA掺杂膜中测量的(c) pS/pR-19-1和(d) pS/pR-19-2的CPL和发射光谱[61]

Figure 20. (a) Structures of 19-1 and 19-2; (b) UV-vis absorption and emission spectra of rac-19-1 (λex=373 nm) and rac-19-2 (λex=373 nm) radicals in n-hexane (c=1.0×10－5 mol/L) (inset: emission photographs under 365 nm UV light); CPL and emission spectra of (c) pS/pR-19-1 and (d) pS/pR-19-2 measured in PMMA-doped films (w=5%) Reproduced with permission.[61] Copyright 2023, the American Chemical Society.

图21. (a) 20-1和20-2的结构; (b)使用长波长紫外灯进行光激发下的滴铸样品照片; (c)它们的光致发光发射光谱(λexc=400 nm, 20 ℃)聚(20-1)(紫色线)、聚(20-2)(蓝色线)和聚[(20-1)-co-(20-2)](橙色线)[63]

Figure 21. (a) Structures of 20-1 and 20-2; (b) Picture of drop-casted samples under photoexcitation using a long-wavelength UV lamp and (c) their photoluminescence emission spectra (λexc=400 nm, 20 ℃) poly(20-1) (purple line), poly(20-2) (blue line), and poly[(20-1)-co-(20-2)]) (orange line) Reproduced with permission.[63] Copyright 2020, the American Chemical Society.

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手性共轭有机三芳基硼(Ar₃B)发光材料研究进展

Recent Progress of Chiral Conjugated Organic Triarylboron (Ar₃B) Luminescent Materials

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