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

doi:10.6023/cjoc202407002

Abstract

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

Cite this article

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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Fig. & Tab. 25

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

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

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	—

Table 1. Photophysical properties of axially chiral molecules

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.

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.

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

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

Table 2. Photophysical properties of helical molecules

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.

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.

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.

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.

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.

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.

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.

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.

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.

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	—

Table 3. Photophysical properties of planar chiral molecules

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.

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.

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.

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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[14]	Yang Yun, Liu Huihui, Liu Xiaobing, Liu Tiantian, Zhu Yuqin, Zhang Anan, Wang Tao, Hua Yuanzhao, Wang Mincan, Mao Guoliang, Liu Lantao. Asymmetric Synthesis of Axial Chiral Vinylarenes Fearturing Oxindole Moiety via Tandem Carbopalladation/C-H Olefination [J]. Chin. J. Org. Chem., 2019, 39(6): 1655-1664.
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手性共轭有机三芳基硼(Ar3B)发光材料研究进展