杂螺烯圆偏振发光材料的研究进展

doi:10.6023/cjoc202504012

摘要/Abstract

杂螺烯是一种具有螺旋手性结构的多环芳烃, 杂螺烯及其衍生物因其独特的光学活性及圆偏振发光特性, 近年来成为手性发光材料领域的研究热点. 通过将主族元素(如N、O、S等)引入到螺烯骨架中, 研究了该策略对分子的电子结构、发光性能及手性光学性质的调控机制, 重点介绍了N、O、S单原子掺杂和B/N、S/N和O/N等多原子掺杂的螺烯在圆偏振发光材料设计中的最新研究进展, 并展望了其在3D显示、信息加密、生物成像等领域的应用潜力. 因此, 深入研究杂螺烯圆偏振发光有机分子的合成、结构及其性质, 对于推动光电子学和材料科学领域的发展具有重要意义.

关键词: 螺烯, 圆偏振发光, 杂原子掺杂, 构效关系, 综述

Heterohelicenes represent a class of polycyclic aromatic hydrocarbons (PAHs) with helically chiral structures, and in recent years these compounds and their derivatives have emerged as a research focus in the field of chiral luminescent materials due to their unique optical properties and circularly polarized luminescence (CPL). This review comprehensively summarizes the modulation mechanisms by which the incorporation of main-group elements (e.g., N, O, S) regulates the electronic structures, luminescence performance, and chiroptical properties of helicenes. The recent advances in the design of CPL materials based on heterohelicenes that are doped with N, O, S or B/N, O/N, S/N is introduced in detail, and their potential applications in 3D displays, information encryption, and bioimaging are prospected. Therefore, studies on the synthesis, structural design, and photophysical properties of heterohelicene-based CPL-active molecules hold significant importance in advances of optoelectronics and materials science.

Key words: helicenes, circularly polarized luminescence, heteroatom doping, structure-property relationship, review

引用此文

孙翠萍, 薛雨婷, 陈磅宽. 杂螺烯圆偏振发光材料的研究进展[J]. 有机化学, 2025, 45(11): 4048-4069.

Cuiping Sun, Yuting Xue, Pangkuan Chen. Recent Advances in Heterohelicene-Based Circularly Polarized Luminescence Materials[J]. Chinese Journal of Organic Chemistry, 2025, 45(11): 4048-4069.

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图/表 28

图1. (a) C的结构; (b) C在CH2Cl2和固态下的CPL光谱(插图: 365 nm紫外灯下的照片); (c) UV-Vis-NIR光谱监测不同量NOSbF6对(P,P)-C (c=5×10－3 mol/L, CH2Cl2/CH3CN)的化学氧化作用(插图: 加入NOSbF6后的溶液照片)[20]

Figure 1. (a) Structures of C; (b) CPL spectra of C both in CH2Cl2 and in the film state (inset: photographs under 365 nm UV lamp); (c) Chemical oxidations of (P,P)-C (c=5×10－3 mol/L, CH2Cl2/CH3CN) with different amounts of NOSbF6 monitored by UV-Vis-NIR absorption spectra (inset: photographs of solutions after addition of NOSbF6)[20]

图2. (a) N7-BMes2和N7-TTM的结构; (b) N7-BMes2和N7-TTM在正己烷(c=1.0×10－5 mol/L)中的紫外-可见吸收(实线)和发射(虚线, λex=377 nm)图谱; (c, d) N7-BMes2 (CH2Cl2)和N7-TTM(正己烷)对映体的CPL光谱[21]

Figure 2. (a) Structures of N7-BMes2 and N7-TTM; (b) UV-vis absorption (solid lines) and emission (dashed lines, λex=377 nm) spectra of N7-BMes2 and N7-TTM in n-hexane (c=1.0×10－5 mol/L); (c, d) CPL spectra of enantiomers for N7-BMes2 (in CH2Cl2) and N7-TTM (in n-hexane)[21]

图3. (a)富电子大环1和2的结构; (b) 1和2在298 K下CH2Cl2中的CPL光谱(1.0×10－5 mol/L); (c)通过UV-vis-NIR吸收光谱监测1 (c=5×10－5 mol/L, CH2Cl2/CH3CN)在不同量NOSbF6作用下的化学氧化反应(插图: 加入NOSbF6后的溶液照片); (d)通过光谱电化学测量监测在施加扫描电压(0~2.5 V)时1在CH2Cl2中进行氧化过程的原位UV-vis-NIR光谱[22]

Figure 3. (a) Structures of the electron-rich macrocycles 1 and 2; (b) Circularly polarized luminescence spectra (1.0×10－5 mol/L) in CH2Cl2 at 298 K of 1 and 2; (c) Chemical oxidations of 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; (d) in situ UV/Vis-NIR spectra monitored by spectroelectrochemical measurements in CH2Cl2 upon the oxidation of 1 at increased scan potentials (0~2.5 V)[22]

图4. (a)双氮杂[7]螺烯3的结构; (b)负曲率氮杂纳米石墨烯4的结构; (c) 3在298 K下, CH2Cl2中的CD和CPL光谱(c=1.0× 10－5 mol/L)[26]

Figure 4. (a) Structure of the double aza[7]helicene 3; (b) Structure of the negatively curved aza-NG 4; (c) CD and CPL spectra for 3 in dichloromethane (c=1.0×10－5 mol/L) at 298 K[26]

图5. (a)氮掺杂纳米石墨烯CPH-1~CPH-3的结构; (b, c) CPH-2和CPH-3在298 K下CH2Cl2中的CD和CPL光谱(1.0×10－5 mol/L)以及|gabs|和glum曲线[30]

Figure 5. (a) Structures of the N-doped helical nonalternant nanographenes CPH-1~CPH-3; (b) CD spectra and |gabs| curves and (c) CPL emission spectra and glum curves of CPH-2 and CPH-3 measured in dichloromethane (1×10－5 mol/L) at 298 K[30]

图6. (a)化合物5、6a、6b和6b-H2的结构; (b~d) 5、6b和6b-H2在298 K下CH2Cl2中的CD(实线)和CPL光谱(虚线)[31]

Figure 6. (a) Structures of compounds 5, 6a, 6b and 6b-H2; (b~d) CD (full line) and CPL (dashed line) spectra of 5, 6b and 6b-H2 in dichloromethane at 298 K[31]

图7. (a)化合物7~10的结构; 在CH2Cl2中的(b) CD光谱, (c)紫外-可见光谱, (d) CPL光谱, 以及(e)荧光光谱(FL) (插图: 在CH2Cl2溶液中, 紫外光(λ=365 nm)照射下P构型化合物的照片)[32]

Figure 7. (a) Structures of compounds 7~10; (b) CD, (c) UV/Vis, (d) CPL, and (e) FL spectra in CH2Cl2 (inset: photographs of dichloromethane solutions of each (P)-helicene under black light (λ=365 nm) are shown)[32]

图8. (a)化合物11~14的结构; (b) 11~13在CH2Cl2溶液中的CD和CPL光谱[33]

Figure 8. (a) Structures of compounds 11~14; (b) CD and CPL spectra of 11~13 in dichloromethane[33]

图9. (a)化合物NHn (n=1~5)的结构; (b)化合物NH2、NH3和NH4的CD和CPL光谱[37]

Figure 9. (a) Structures of compounds NHn (n=1~5); (b) CD and CPL spectra of NH2, NH3 and NH4[37]

图10. (a)化合物[n]AH-Bum [m=(n－1)/2]、[9]AH、15、15-Et、15-Bu的结构; (b)室温下四氢呋喃溶液中化合物[9]AH-Bu4 (黑), [11]AH-Bu5 (红), [13]AH-Bu6 (蓝)和[15]AH-Bu6 (绿)的CD和CPL光谱; (c)化合物15-Et和15-Bu的CD和CPL光谱[41-42]

Figure 10. (a) Structures of compounds [n]AH-Bum [m=(n－1)/2], [9]AH, 15, 15-Et and 15-Bu; (b) CD and CPL spectra of [9]AH-Bu4 (black), [11]AH-Bu5 (red), [13]AH-Bu6 (blue), and [15]AH-Bu6 (green) in THF at room temperature; (c) CD and CPL spectra of 15-Et and 15-Bu[41-42]

图11. (a)化合物16的结构; (b)化合物16的CD光谱和(M)-16的模拟光谱(黑色虚线); (c)化合物16的CPL光谱[45]

Figure 11. (a) Structure of the compound 16; (b) CD spectra of compound 16 and simulated spectrum of (M)-16 (black dash line); (c) CPL spectra of compound 16[45]

图12. (a)化合物17、18的结构; (b)化合物17、18在CH2Cl2中的紫外-可见光谱(底部)和CD光谱(顶部); (c)化合物17、18在CH2Cl2中的荧光(底部)和CPL(顶部)光谱(1.0×10－5 mol/L)[46]

Figure 12. (a) Structures of compounds 17 and 18; (b) UV-vis (bottom) and CD (top) spectra of 17 and 18 in dichloromethane; (c) Fluorescence (bottom) and CPL (top) spectra of 17 and 18 in dichloromethane (1.0×10－5 mol/L)[46]

图13. (a) 化合物TB[n]H (n=5~8)的结构; (b) TB[7]H在2-甲基四氢呋喃中CD和CPL光谱[47]

Figure 13. (a) Structures of compounds TB[n]H (n=5~8); (b) CD and CPL spectra of TB[7]H in 2-MeTHF[47]

图14. (a)化合物TS[7]H、TT[7]H、TH[7]H的结构; (b)化合物TS[7]H、TT[7]H、TH[7]H在二氯甲烷溶液中的CD (c=6.1× 10－5 mol/L)和CPL (c=1×10－3 mol/L)光谱[48]

Figure 14. (a) Structures of compounds TS[7]H, TT[7]H, TH[7]H; (b) CD (c=6.1×10－5 mol/L) and CPL (c=1×10－3 mol/L) spectra of TS[7]H, TT[7]H-2, and TH[7]H in dichloromethane[48]

图15. (a)化合物19的结构; 19在CH2Cl2溶液中的(b) CD和(c) CPL光谱(c=1×10－5 mol/L)[49]

Figure 15. (a) Structures of the compound 19; (b) CD and (c) CPL spectra of 19 in CH2Cl2 (c=1.0×10－5 mol/L)[49]

图16. (a)化合物DO7H、DT7H、DS7H的结构; (b)化合物DTH1、DTH2的结构; (c~d) DO7H、DT7H、DS7H、DTH1、DTH2在CH2Cl2溶液中的CD和CPL光谱(c=1×10－5 mol/L)[53-54]

Figure 16. (a) Structures of compounds DO7H, DT7H, DS7H; (b) Structures of compounds DTH1, DTH2; (c~d) CD and CPL spectra of DO7H, DT7H, DS7H, DTH1, DTH2 in dichloromethane (c=1.0×10－5 mol/L)[53-54]

图17. (a)化合物20的结构; (b)化合物20的CD和CPL光谱[红色虚线表示化合物(P,P,P)-20在B3LYP/6-311G(d,p)水平下的TD-DFT模拟的CD光谱][55]

Figure 17. (a) Structure of the compound 20; (b) CD and CPL spectra of the compound 20 (The red dotted line shows the CD spectrum for (P,P,P)-20 simulated by TD-DFT at the B3LYP/6-311G (d, p) level)[55]

图18. (a)化合物21~23的结构; (b)化合物21~23在CH2Cl2溶液中的CD光谱; (c)化合物21~23在CH2Cl2溶液中的CPL光谱[56]

Figure 18. (a) Structures of compounds 21~23; (b) CD spectra of 21~23 in dichloromethane; (c) CPL spectra of 21~23 in dichloromethane[56]

图19. (a)化合物A、A'的结构; (b)化合物A、A'的CD和CPL光谱[58]

Figure 19. (a) Structures of compounds A, A'; (b) CD and CPL spectra of compounds A, A'[58]

图20. (a)化合物24、25、2-C1、2-C2、3-C2的结构; (b)化合物24、25在CH2Cl2溶液中的CD和CPL光谱; (c)化合物2-C1, 2-C2, 3-C2的CD和CPL光谱[62-63]

Figure 20. (a) Structures of compounds 24, 25, 2-C1, 2-C2, 3-C2; (b) CD and CPL spectra of compounds 24, 25 in dichloromethane; (c) CD and CPL spectra of compounds 2-C1, 2-C2, 3-C2[62-63]

图21. (a)化合物BN[9]H的结构; (b)化合物BN[9]H在甲苯溶液中的CD、CPL、gabs和glum图[65]

Figure 21. (a) Structures of the compound BN[9]H; (b) CD and CPL spectra, corresponding gabs and glum values of the compound BN[9]H in toluene[65]

图22. (a)化合物[8]HAB、[10]HAB、E[10]HAB-A、E[10]HAB-B和E[10]HAB-C的结构; (b)化合物[8]HAB和[10]HAB在CH2Cl2溶液中的CD和CPL光谱; 化合物E[10]HAB-A、E[10]HAB-B和E[10]HAB-C在CH2Cl2溶液中的(c) CD和(d) CPL光谱[67-68]

Figure 22. (a) Structures of compounds [8]HAB, [10]HAB, E[10]HAB-A, E[10]HAB-B and E[10]HAB-C; (b) CD and CPL spectra of compounds [8]HAB and [10]HAB in dichloromethane; (c) CD and (d) CPL spectra of E[10]HAB-A, E[10]HAB-B and E[10]HAB-C in dichloromethane[67-68]

图23. (a) 化合物2B及其氟离子加合物的分子结构; (b)化合物2B的CD和CPL光谱[72]

Figure 23. (a) Structures of the compound 2B and fluoride adduct; (b) CD and CPL spectra of the compound 2B[72]

图24. (a)化合物BN-HC、BiBN-HC和BiBN-BiHC的结构; BN掺杂[6]螺烯在甲苯溶液中的(b) CD和(c) CPL光谱(c=3.0×10－5 mol/L)[73]

Figure 24. (a) Structures of compounds BN-HC, BiBN-HC and BiBN-BiHC; (b) CD and (c) CPL spectra of BN-heterocycle-fused helicenes in toluene (c=3.0×10－5 mol/L)[73]

图25. (a) 化合物H1-Me4的结构; H1-Me4的(b) CD和(c) CPL光谱[74]

Figure 25. (a) Structure of the compound H1-Me4; (b) CD and (c) CPL spectra of H1-Me4[74]

图26. (a)化合物26和27的结构; (b) 27的CD和CPL光谱[75]

Figure 26. (a) Structures of compounds 26 and 27; (b) CD and CPL spectra of 27[75]

图27. (a)化合物SNSN-S和(SNSN-S)2的结构; (b) SNSN-S和(c) (SNSN-S)2在四氢呋喃溶液中的CD光谱; (d) SNSN-S在四氢呋喃溶液中的CPL光谱[76]

Figure 27. (a) Structures of compounds SNSN-S and (SNSN-S)2; CD spectra of (b) SNSN-S and (c) (SNSN-S)2 in THF; (d) CPL spectra of SNSN-S in THF[76]

Compound	Φ_F	g_abs/10^－3	g_lum/10^－3	Compound	Φ_F	g_abs/10^－3	g_lum/10^－3
C	0.86	0.48	0.22	19	0.48	7.5	0.59
rac-N7-Bmes2	0.32	4.17	3.39	DO7H	0.71	10	0.75
rac-N7-TTM	0.5	2.7	3.57	DT7H	0.43	14	1.2
1	0.26	33	1.5	DSTH	0.31	7.2	1.1
2	0.99	14	5	DTH1	0.83	4	2.2
3	0.45	—	2.4	DTH2	0.91	5.3	2.1
CPH-3	0.32	10	7	20	0.04	6.1	1.8
5	0.47	3.5	0.94	21	0.53	4.6	0.5
6a	0.01	2.5	—	22	0.26	4	1.6
6b	0.12	1.9	1.6	23	0.1	3.6	2.1
7	0.44	4.7	2.3	A	3.1	—	1.58
8	0.32	3.9	1.9	A'	3.5	—	4.3
9	0.61	2.1	0.74	2B	—	1.6	0.47
10	0.54	2.5	1.3	2B·F	—	3	1.7
11	0.1	4.7	3.5	BN-HC	0.11	0.6	—
12	0.22	3.7	2.4	BiBH-HC	0.2	2.19	1.95
13	—	2.8	—	BiBH-BiHC	0.87	2.15	2.06
14	—	—	—	24	0.72	1.7	1.5
9AH-Bu₄	0.16	5.6	4.5	25	0.85	1.3	1.1
11AH-Bu₅	0.16	4.2	4.2	2-C₁	0.85	1	0.75
13AH-Bu₆	0.09	4.2	1.7	2-C₂	0.81	2.7	1.9
15AH-Bu₆	0.07	1.7	5.7	3-C₂	0.59	4.1	2.3
15	0.07	—	—	BN[9]H	0.98	—	5.8
16-Et	0.35	2.4	1	[8]HAB	0.31	36	24
16-Bu	0.35	2.3	1	[10]HAB	0.24	61	48
16	0.4	2.98	4.3	E[10]HAB-A	0.82	24	17
17	0.2	—	4.6	E[10]HAB-B	0.67	11	11
18	3.5	—	12.5	E[10]HAB-C	0.72	12	8
TB[7]H	0.19	3	15	H1-M4	0.17	3.3	3.5
TS[7]H	—	1	—	SNSN-S	—	—	1.2

表1. 综述中所有化合物的发光量子效率、吸收不对称因子和发光不对称因子

Table 1. Luminescence quantum efficiency (ΦF), absorption asymmetry factor (gabs) and luminescence asymmetry factor (glum) of all compounds

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