Research Progress on the Synthesis and Optoelectronic Properties of Helicene Derivatives

doi:10.6023/cjoc202503035

Abstract

Helicenes and their derivatives represent a class of non-planar nanocarbon molecules formed by ortho-fused aromatic rings. Their unique helical structure endows helicenes with remarkable chiral optical activity, exhibiting circular dichroism (CD) and circularly polarized luminescence (CPL) properties. These characteristics make helicenes highly promising for applications in optical materials and biosensors. Heteroatom doping is an effective strategy to enhance the performance of helicenes. By introducing heteroatoms such as nitrogen, boron, oxygen, or sulfur, the electronic structure of helicenes can be precisely tuned, significantly improving their chiral optical properties and quantum yield. The latest research progress in this field over the past three years is summarized, focusing on the design, synthesis, and performance optimization strategies of all-carbon helicenes and heteroatom-doped helicene nano-carbon molecules. Future development directions are also discussed.

Key words: helicene, molecular nanocarbon, chiral material, circularly polarized luminescence, heteroatom doping

Cite this article

Qing-Yue Song, Guiyi Yang, Yue Zhang, Zijie Qiu. Research Progress on the Synthesis and Optoelectronic Properties of Helicene Derivatives[J]. Chinese Journal of Organic Chemistry, 2025, 45(11): 3953-3973.

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References 66

[1]	Meisenheimer, J.; Witte, K. Chem. Ber. 1903, 36, 4153. doi: 10.1002/cber.v36:4
[2]	Martin, R. H. Angew. Chem., Int. Ed. 1974, 13, 649.
[3]	Groen, M. B.; Stulen, G.; Visser, G. J.; Wynberg, H. J. Am. Chem. Soc. 1970, 92, 7218. doi: 10.1021/ja00727a043
[4]	Wynberg, H.; Groen, M. B. J. Am. Chem. Soc. 1970, 92, 6664. doi: 10.1021/ja00725a060
[5]	Dopper, J. H.; Oudman, D.; Wynberg, H. J. Am. Chem.Soc. 1973, 95, 3692. doi: 10.1021/ja00792a037
[6]	Laarhoven, W. H.; Nivard, R. J. F. Tetrahedron 1976, 32, 2445. doi: 10.1016/0040-4020(76)87032-9
[7]	Borkent, J. H.; Laarhoven, W. H. Tetrahedron 1978, 34, 2565. doi: 10.1016/0040-4020(78)88387-2
[8]	Sudhakar, A.; Katz, T. J. Tetrahedron Lett. 1986, 27, 2231. doi: 10.1016/S0040-4039(00)84494-9
[9]	Liu, L. B.; Katz, T. J. Tetrahedron Lett. 1991, 32, 6831. doi: 10.1016/0040-4039(91)80418-6
[10]	Willmore, N. D.; Liu, L. B.; Katz, T. J. Angew.Chem., Int. Ed. 1992, 31, 1093.
[11]	Gilbert, A. M.; Katz, T. J.; Geiger, W. E.; Robben, M. P.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3199. doi: 10.1021/ja00061a019
[12]	Liberko, C. A.; Miller, L. L.; Katz, T. J.; Liu, L. B. J. Am. Chem. Soc. 1993, 115, 2478. doi: 10.1021/ja00059a050
[13]	Meurer, K. P.; V€ogtle, F. Top. Curr. Chem. 1985, 127, 1.
[14]	Cahn, R. S.; Ingold, C.; Prelog, V. Angew. Chem., Int. Ed. 1966, 5, 385.
[15]	Zhang, Y.; Yu, S.; Han, B.; Zhou, Y.; Zhang, X.; Gao, X.; Tang, Z. Matter 2022, 5, 837. doi: 10.1016/j.matt.2022.01.001
[16]	Appiarius, Y.; Míguez-Lago, S.; Puylaert, P.; Wolf, N.; Kumar, S.; Molkenthin, M.; Miguel, D.; Neudecker, T.; Juríček, M.; Campaña, A. G.; Staubitz, A. Chem. Sci. 2024, 15, 466. doi: 10.1039/d3sc02685j pmid: 38179512
[17]	Qiu, Z.; Asako, S.; Hu, Y.; Ju, C.-W.; Liu, T.; Rondin, L.; Schollmeyer, D.; Lauret, J.-S.; Müllen, K.; Narita, A. J. Am. Chem. Soc. 2020, 142, 14814. doi: 10.1021/jacs.0c05504
[18]	Gu, Y.; Qiu, Z.; Müllen, K. J. Am. Chem. Soc. 2022, 144, 1149.
[19]	Wang, Q.; Lim, G.; Gopalakrishna, T. Y.; Han, Y.; Chi, C. Asian J. Org. Chem. 2018, 7, 1864. doi: 10.1002/ajoc.v7.9
[20]	Li, J. K.; Chen, X. Y.; Guo, Y. L.; Wang, X. C.; Sue, A. C.; Cao, X. Y.; Wang, X. Y. J. Am. Chem. Soc. 2021, 143,
[21]	Wang, Y.; Yin, Z.; Zhu, Y.; Gu, J.; Li, Y.; Wang, J. Angew. Chem., Int. Ed. 2019, 58, 587. doi: 10.1002/anie.v58.2
[22]	Zhu, Y.; Xia, Z.; Cai, Z.; Yuan, Z.; Jiang, N.; Li, T.; Wang, Y.; Guo, X.; Li, Z.; Ma, S.; Zhong, D.; Li, Y.; Wang, J. J. Am. Chem. Soc. 2018, 140, 4222. doi: 10.1021/jacs.8b01447
[23]	Zhu, Y.; Guo, X.; Li, Y.; Wang, J. J. Am. Chem. Soc. 2019, 141, 5511. doi: 10.1021/jacs.9b01266
[24]	Chen, X.-Y.; Li, J.-K.; Wang, X.-Y. Chin. J. Org. Chem. 2021, 41, 4105 (in Chinese). doi: 10.6023/cjoc202107063
	(陈星宇, 李继坤, 王小野, 有机化学, 2021, 41, 4105.) doi: 10.6023/cjoc202107063
[25]	Pun, S. H.; Cheung, K. M.; Yang, D.; Chen, H.; Wang, Y.; Kershaw, S. V.; Miao, Q. Angew. Chem., Int. Ed. 2022, 61, e202113203.
[26]	Wang, J.; Shen, C.; Zhang, G.; Gan, F.; Ding, Y.; Qiu, H. Angew. Chem., Int. Ed. 2022, 61, e202115979.
[27]	Li, J. K.; Chen, X. Y.; Zhao, W. L.; Guo, Y. L.; Zhang, Y.; Wang, X. C.; Sue, A. C. H.; Cao, X. Y.; Li, M.; Chen, C. F.; Wang, X. Y. Angew. Chem., Int. Ed. 2023, 62, e202215367.
[28]	Huo, G. F.; Xu, W. T.; Hu, J.; Han, Y.; Fan, W.; Wang, W.; Sun, Z.; Yang, H. B.; Wu, J. Angew. Chem., Int. Ed. 2025, 64, e202416707.
[29]	Shen, Y. J.; Yao, N. T.; Diao, L. N.; Yang, Y.; Chen, X. L.; Gong, H. Y. Angew. Chem., Int. Ed. 2023, 62, e202300840.
[30]	Izquierdo-García, P.; Fernández-García, J. M.; Medina Rivero, S.; Šámal, M.; Rybáček, J.; Bednárová, L.; Ramírez-Barroso, S.; Ramírez, F. J.; Rodríguez, R.; Perles, J.; García-Fresnadillo, D.; Crassous, J.; Casado, J.; Stará, I. G.; Martín, N. J. Am. Chem. Soc. 2023, 145, 11599. doi: 10.1021/jacs.3c01088 pmid: 37129470
[31]	Cui, W.; Jin, Z.; Fu, W.; Shen, C. Chin. Chem. Lett. 2024, 35, 109667. doi: 10.1016/j.cclet.2024.109667
[32]	Zhu, K. L.; Li, Z. A.; Liang, J.; Zou, K. L.; Shen, Y. J.; Gong, H. Y. Angew. Chem., Int. Ed. 2024, 63, e202409713.
[33]	Duan, C.; Zhang, J.; Xiang, J.; Yang, X.; Gao, X. Angew. Chem., Int. Ed. 2022, 61, e202201494.
[34]	Yang, L.; Ju, Y. Y.; Medel, M. A.; Fu, Y.; Komber, H.; Dmitrieva, E.; Zhang, J. J.; Obermann, S.; Campaña, A. G.; Ma, J.; Feng, X. Angew. Chem., Int. Ed. 2023, 62, e202216193.
[35]	Tan, J.; Xu, X.; Liu, J.; Vasylevskyi, S.; Lin, Z.; Kabe, R.; Zou, Y.; Müllen, K.; Narita, A.; Hu, Y. Angew. Chem., Int. Ed. 2023, 62, e202218494.
[36]	Yu, Y.; Wang, L.; Wang, C.; Liu, F.; Ling, H.; Liu, J. Small Sci. 2023, 3, 2300040. doi: 10.1002/smsc.v3.8
[37]	Dong, Y.; Zhang, Z.; Hashikawa, Y.; Meng, H.; Bai, F.; Itami, K.; Chao, L. Angew. Chem., Int. Ed. 2024, 63, e202406927.
[38]	Li, C.; Zhang, C.; Li, P.; Jia, Y.; Duan, J.; Liu, M.; Zhang, N.; Chen, P. Angew. Chem., Int. Ed. 2023, 62, e202302019.
[39]	Matsuo, Y.; Gon, M.; Tanaka, K.; Seki, S.; Tanaka, T. J. Am. Chem. Soc. 2024, 146, 17428. doi: 10.1021/jacs.4c05156
[40]	Gan, F.; Zhang, G.; Liang, J.; Shen, C.; Qiu, H. Angew. Chem., Int. Ed. 2024, 63, e202320076.
[41]	Dongre, S. D.; Venugopal, G.; Kumar, V.; Jadhav, A. B.; Kumar, J.; Babu, S. S. Angew. Chem., Int. Ed. 2025, 64, e202420767.
[42]	Wang, X. Y.; Bai, J.; Shen, Y. J.; Li, Z. A.; Gong, H. Y. Angew. Chem., Int. Ed. 2025, 64, e202417745.
[43]	Kumar, V.; Venugopal, G.; Jadhav, A. B.; Dongre, S. D.; Gonnade, R.; Kumar, J.; Ruer, P. C.; Hupp, B.; Steffen, A.; Babu, S. S. Angew. Chem., Int. Ed. 2025, 64, e202422125.
[44]	Wu, Y.-F.; Ying, S.-W.; Su, L.-Y.; Du, J.-J.; Zhang, L.; Chen, B.-W.; Tian, H.-R.; Xu, H.; Zhang, M.-L.; Yan, X.; Zhang, Q.; Xie, S.-Y.; Zheng, L.-S. J. Am. Chem. Soc. 2022, 144, 10736. doi: 10.1021/jacs.2c00794 pmid: 35671378
[45]	Hatakeyama, T.; Shiren, K.; Nakajima, K.; Nomura, S.; Nakatsuka, S.; Kinoshita, K.; Ni, J.; Ono, Y.; Ikuta, T. Adv. Mater. 2016, 28, 2777. doi: 10.1002/adma.v28.14
[46]	Li, J. K.; Chen, X. Y.; Guo, Y. L.; Wang, X. C.; Sue, A. C.; Cao, X. Y.; Wang, X. Y. J. Am. Chem. Soc. 2021, 143, 17958. doi: 10.1021/jacs.1c09058
[47]	Li, J. K.; Zhang, M. Y.; Zeng, L.; Huang, L.; Wang, X. Y. Angew. Chem., Int. Ed. 2023, 62, e202303093.
[48]	Meng, G.; Zhou, J.; Han, X. S.; Zhao, W.; Zhang, Y.; Li, M.; Chen, C. F.; Zhang, D.; Duan, L. Adv. Mater. 2023, 36, 2307420. doi: 10.1002/adma.v36.5
[49]	Wang, Q.; Yuan, L.; Qu, C.; Huang, T.; Song, X.; Xu, Y.; Zheng, Y. X.; Wang, Y. Adv. Mater. 2023, 35, 2305125. doi: 10.1002/adma.v35.42
[50]	Zhang, F.; Rauch, F.; Swain, A.; Marder, T. B.; Ravat, P. Angew. Chem., Int. Ed. 2023, 62, e202218965.
[51]	Zhang, F.; Brancaccio, V.; Saal, F.; Deori, U.; Radacki, K.; Braunschweig, H.; Rajamalli, P.; Ravat, P. J. Am. Chem. Soc. 2024, 146, 29782. doi: 10.1021/jacs.4c11404
[52]	Ju, Y. Y.; Xie, L. E.; Xing, J. F.; Deng, Q. S.; Chen, X. W.; Huang, L. X.; Nie, G. H.; Tan, Y. Z.; Zhang, B. Angew. Chem., Int. Ed. 2025, 64, e202414383.
[53]	Guo, W. C.; Zhao, W. L.; Tan, K. K.; Li, M.; Chen, C. F. Angew. Chem., Int. Ed. 2024, 63, e202401835.
[54]	Zhuang, W.; Hung, F. F.; Che, C. M.; Liu, J. Angew. Chem., Int. Ed. 2024, 63, e202406497.
[55]	Maeda, C.; Michishita, S.; Yasutomo, I.; Ema, T. Angew. Chem., Int. Ed. 2025, 64, e202418546.
[56]	Liu, Y.; Yuan, L.; Fan, Z.; Yang, J.; Wang, Y.; Dou, C. Chem. Sci. 2024, 15, 12819. doi: 10.1039/D4SC03124E
[57]	Chang, H.; Liu, H.; Dmitrieva, E.; Chen, Q.; Ma, J.; He, P.; Liu, P.; Popov, A. A.; Cao, X. Y.; Wang, X. Y.; Zou, Y.; Narita, A.; Müllen, K.; Peng, H.; Hu, Y. Chem. Commun. 2020, 56, 15181. doi: 10.1039/D0CC06970A
[58]	Ju, Y. Y.; Luo, H.; Li, Z. J.; Zheng, B. H.; Xing, J. F.; Chen, X. W.; Huang, L. X.; Nie, G. H.; Zhang, B.; Liu, J.; Tan, Y. Z. Angew. Chem., Int. Ed. 2024, 63, e202402621.
[59]	Zhou, L.; Liu, H.; Tan, J.; Liu, C.; Cao, X. Y.; Narita, A.; Hu, Y. Chem.-Asian J. 2022, 17, e202200336.
[60]	Yang, W. W.; Ren, Z. H.; Feng, J.; Lv, Z. B.; Cheng, X.; Zhang, J.; Du, D.; Chi, C.; Shen, J. J. Angew. Chem., Int. Ed. 2024, 63, e202412681.
[61]	Wu, H.; Hanayama, H.; Coehlo, M.; Gu, Y.; Wu, Z.-H.; Takebayashi, S.; Jakob, G.; Vasylevskyi, S.; Schollmeyer, D.; Kläui, M.; Pieters, G.; Baumgarten, M.; Müllen, K.; Narita, A.; Qiu, Z. J. Am. Chem. Soc. 2024, 146, 7480. doi: 10.1021/jacs.3c12840
[62]	Ma, Y.; Zhou, L.; Tan, J.; Sun, W.; Zou, Y.; Hu, Y. Adv. Opt. Mater. 2024, 13, 2402446. doi: 10.1002/adom.v13.6
[63]	Wu, Y. F.; Ying, S. W.; Liao, S. D.; Zhang, L.; Du, J. J.; Chen, B. W.; Tian, H. R.; Xie, F. F.; Xu, H.; Deng, S. L.; Zhang, Q.; Xie, S. Y.; Zheng, L. S. Angew. Chem., Int. Ed. 2022, 61, e202204334.
[64]	Qiu, Z.; Ju, C.-W.; Frédéric, L.; Hu, Y.; Schollmeyer, D.; Pieters, G.; Müllen, K.; Narita, A. J. Am. Chem. Soc. 2021, 143, 4661. doi: 10.1021/jacs.0c13197
[65]	Yu, Y.; Wang, C.; Hung, F.-F.; Chen, C.; Pan, D.; Che, C.-M.; Liu, J. J. Am. Chem. Soc. 2024, 146, 22600. doi: 10.1021/jacs.4c06997
[66]	Yu, Y.; Wang, C.; Hung, F. F.; Jiang, L.; Che, C. M.; Liu, J. Angew. Chem., Int. Ed. 2025, 64, e202501645.

Compd.	λ_PL/nm	Φ_F/%	\|g_lum\|/10^－3	\|g_abs\|/10^－3	B_CPL/(L• mol^－1•cm^－1)	Ref.	Compd.	λ_PL/nm	Φ_F/%	\|g_lum\|/10^－3	\|g_abs\|/10^－3	B_CPL/(L• mol^－1•cm^－1)	Ref.
1	977	4.6	—	—	—	[25]	44	527	90	0.52	—	—	[49]
2-1	625	10.9	1.5	—	—	[26]	45	520	85	1.1	1.3	36	[50]
2-2	625	8.2	1.5	—	—	[26]	46-C₂	543	72	1.5	1.7	65	[50]
3	652	93	0.8	7.0	32	[27]	46-C_S	546	78	—	—	—	[50]
4	654	31.9	4.5	3.0	—	[28]	47	484	59	2.3	4.1	—	[51]
5	812	15.0	1.3	8.5	—	[28]	48	500	85	1.9	2.7	—	[51]
6	817	13.7	1.4	3.0	—	[28]	49	508	81	0.75	1.0	—	[51]
7	1010	6.5	—	1.2	—	[28]	50	595	68.3	2.7	7.4	41.5	[52]
8	684	10	45.2	27.6	304	[29]	51	585	65.7	2.5	8.6	45.8	[52]
9	575	22	36	36	81	[30]	52	598	74.3	2.7	3.1	58.7	[52]
10	543	10	10	16	21	[30]	53	622	10.8	2.9	4.7	2.0	[52]
11	528	11	9	10	28	[30]	54	563	27.3	—	—	—	[52]
12	519	29	3	—	41	[31]	55	595	1.7	5.0	6.6	4.0	[52]
13	572	52	5	—	305	[31]	56	578	98	5.8	5.6	220	[53]
14	626	18.3	14.1	10.8	254	[32]	57	584	51	—	—	—	[54]
15	589	15.6	2.6	3.7	6.35	[32]	58	648	68	—	—	—	[54]
16	481	<10	—	—	—	[33]	59	520	88	—	—	—	[54]
17	499	<10	—	22	—	[33]	60	600	48	—	—	—	[54]
18	463	<10	—	21	—	[33]	61	660	22	—	—	—	[54]
19	602	32	1.3	6.6	—	[34]	62	493	—	0.47	1.6	—	[55]
20	635	18	—	19	—	[35]	62-F	502	—	1.7	3.0	—	[55]
21	—	—	—	—	—	[36]	63	618	22	—	—	—	[56]
22	—	—	—	—	—	[36]	64	—	—	—	—	—	[56]
23	612	58	0.78	6.9	—	[37]	65	511	71	0.75	—	—	[57]
24	583	86	0.22	0.48	13.2	[38]	66	535	48.5	0.6	5.2	10.8	[58]
25	423	21	4.5	5.6	—	[39]	67	542	3.4	1.5	3.3	1.7	[58]
26	459	11	1.7	4.2	—	[39]	68	575	53.9	0.5	4.6	13.9	[58]
27	483	18	—	—	—	[39]	69	590	26.2	1.6	4.0	14.7	[58]
28	452	17	4.2	4.2	—	[39]	70	594	10.2	2.1	3.6	7.1	[58]
29	466	9	5.7	1.7	—	[39]	71	558	43	1.1	14	—	[59]
30	508	8	—	—	—	[39]	72	614	31	1.2	7.2	—	[59]
31	625	—	17	—	—	[40]	73	666	48	0.59	7.5	5.71	[60]
32	517	—	2	—	—	[40]	74	—	—	—	—	—	[61]
33	646	44	0.73	1.24	14.13	[41]	75	569	83	2.2	4.0	84.9	[62]
34	576	79	5.5	2.99	145.99	[41]	76	583	91	2.3	5.3	65	[62]
35	628	40	0.43	2.98	32.5	[42]	77-1	778	14	—	—	—	[63]
36	497	68	—	—	—	[43]	77-2	769	11	—	—	—	[63]
37	542	75	1.12	3.91	45.77	[43]	78	495	25	0.77	1.24	1.1	[64]
38	770	28	—	—	—	[44]	79	528	41	7.44	10.58	12.6	[64]
39	660	100	2	33	28.5	[46]	80	409	31	24	36	294	[65]
40	684	99	2	31	37.1	[46]	81	430	24	48	61	292	[65]
41	696	90	2	26	40	[46]	82	515	82	17	24	583	[66]
42	737	60	—	—	—	[47]	83	529	67	11	11	374	[66]
43	617	96	1.4	2	20.8	[48]	84	535	72	8	12	349	[66]

Compd.	λ_PL/nm	Φ_F/%	\|g_lum\|/10^－3	\|g_abs\|/10^－3	B_CPL/(L• mol^－1•cm^－1)	Ref.	Compd.	λ_PL/nm	Φ_F/%	\|g_lum\|/10^－3	\|g_abs\|/10^－3	B_CPL/(L• mol^－1•cm^－1)	Ref.
1	977	4.6	—	—	—	[25]	44	527	90	0.52	—	—	[49]
2-1	625	10.9	1.5	—	—	[26]	45	520	85	1.1	1.3	36	[50]
2-2	625	8.2	1.5	—	—	[26]	46-C₂	543	72	1.5	1.7	65	[50]
3	652	93	0.8	7.0	32	[27]	46-C_S	546	78	—	—	—	[50]
4	654	31.9	4.5	3.0	—	[28]	47	484	59	2.3	4.1	—	[51]
5	812	15.0	1.3	8.5	—	[28]	48	500	85	1.9	2.7	—	[51]
6	817	13.7	1.4	3.0	—	[28]	49	508	81	0.75	1.0	—	[51]
7	1010	6.5	—	1.2	—	[28]	50	595	68.3	2.7	7.4	41.5	[52]
8	684	10	45.2	27.6	304	[29]	51	585	65.7	2.5	8.6	45.8	[52]
9	575	22	36	36	81	[30]	52	598	74.3	2.7	3.1	58.7	[52]
10	543	10	10	16	21	[30]	53	622	10.8	2.9	4.7	2.0	[52]
11	528	11	9	10	28	[30]	54	563	27.3	—	—	—	[52]
12	519	29	3	—	41	[31]	55	595	1.7	5.0	6.6	4.0	[52]
13	572	52	5	—	305	[31]	56	578	98	5.8	5.6	220	[53]
14	626	18.3	14.1	10.8	254	[32]	57	584	51	—	—	—	[54]
15	589	15.6	2.6	3.7	6.35	[32]	58	648	68	—	—	—	[54]
16	481	<10	—	—	—	[33]	59	520	88	—	—	—	[54]
17	499	<10	—	22	—	[33]	60	600	48	—	—	—	[54]
18	463	<10	—	21	—	[33]	61	660	22	—	—	—	[54]
19	602	32	1.3	6.6	—	[34]	62	493	—	0.47	1.6	—	[55]
20	635	18	—	19	—	[35]	62-F	502	—	1.7	3.0	—	[55]
21	—	—	—	—	—	[36]	63	618	22	—	—	—	[56]
22	—	—	—	—	—	[36]	64	—	—	—	—	—	[56]
23	612	58	0.78	6.9	—	[37]	65	511	71	0.75	—	—	[57]
24	583	86	0.22	0.48	13.2	[38]	66	535	48.5	0.6	5.2	10.8	[58]
25	423	21	4.5	5.6	—	[39]	67	542	3.4	1.5	3.3	1.7	[58]
26	459	11	1.7	4.2	—	[39]	68	575	53.9	0.5	4.6	13.9	[58]
27	483	18	—	—	—	[39]	69	590	26.2	1.6	4.0	14.7	[58]
28	452	17	4.2	4.2	—	[39]	70	594	10.2	2.1	3.6	7.1	[58]
29	466	9	5.7	1.7	—	[39]	71	558	43	1.1	14	—	[59]
30	508	8	—	—	—	[39]	72	614	31	1.2	7.2	—	[59]
31	625	—	17	—	—	[40]	73	666	48	0.59	7.5	5.71	[60]
32	517	—	2	—	—	[40]	74	—	—	—	—	—	[61]
33	646	44	0.73	1.24	14.13	[41]	75	569	83	2.2	4.0	84.9	[62]
34	576	79	5.5	2.99	145.99	[41]	76	583	91	2.3	5.3	65	[62]
35	628	40	0.43	2.98	32.5	[42]	77-1	778	14	—	—	—	[63]
36	497	68	—	—	—	[43]	77-2	769	11	—	—	—	[63]
37	542	75	1.12	3.91	45.77	[43]	78	495	25	0.77	1.24	1.1	[64]
38	770	28	—	—	—	[44]	79	528	41	7.44	10.58	12.6	[64]
39	660	100	2	33	28.5	[46]	80	409	31	24	36	294	[65]
40	684	99	2	31	37.1	[46]	81	430	24	48	61	292	[65]
41	696	90	2	26	40	[46]	82	515	82	17	24	583	[66]
42	737	60	—	—	—	[47]	83	529	67	11	11	374	[66]
43	617	96	1.4	2	20.8	[48]	84	535	72	8	12	349	[66]

螺烯衍生物的合成及其光电性质研究进展