Advances in Fluorinated Organometallic Complexes with Aggregation-Induced Emission Characteristics

doi:10.6023/cjoc202007015

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 504-520.DOI: 10.6023/cjoc202007015 Previous Articles Next Articles

Review

具有聚集诱导发光特性的含氟有机金属配合物的研究进展

秦成远^a, 苗金玲^b, 聂永^a^,^*(), 刘威^a, 高迎^a, 李天瑞^a, 蒋绪川^a^,^*()

a 济南大学智能材料与工程研究院济南 250022
b 济南大学化学化工学院山东省氟化学化工材料重点实验室济南 250022

收稿日期:2020-07-05 修回日期:2020-08-18 发布日期:2020-09-16
通讯作者: 聂永, 蒋绪川
作者简介:
* Corresponding authors. E-mail: chm_niey@ujn.edu.cn; ism_jiangxc@ujn.edu.cn
基金资助:
山东省自然科学基金(ZR2017LB008); 山东省自然科学基金(ZR2020MB001); 济南大学科技计划(XKY1906); 山东莘纳智能新材料有限公司资助项目

Advances in Fluorinated Organometallic Complexes with Aggregation-Induced Emission Characteristics

Chengyuan Qin^a, Jinling Miao^b, Yong Nie^a^,^*(), Wei Liu^a, Ying Gao^a, Tianrui Li^a, Xuchuan Jiang^a^,^*()

a Institute for Smart Materials & Engineering, University of Jinan, Jinan 250022
b Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022

Received:2020-07-05 Revised:2020-08-18 Published:2020-09-16
Contact: Yong Nie, Xuchuan Jiang
Supported by:
the Natural Science Foundation of Shandong Province(ZR2017LB008); the Natural Science Foundation of Shandong Province(ZR2020MB001); the Science and Technology Program of University of Jinan(XKY1906); Shandong Shenna Smart Advanced Materials Co.,Ltd.

In recent years, the compounds with aggregation-induced emission (AIE) characteristics have received increasing attention because they exhibit much higher luminescence quantum yields in aggregation or solid states than in solution. Due to the presence of the fluorine atom(s), fluorinated functional compounds generally have unique structures, and physical, chemical and biological properties. Herein, the luminescent organometallic complexes with AIE characteristics having fluorine-containing ligands are summarized, according to the types of central metal atoms and ligands. Such organometallic complexes are mainly those of iridium, platinum and gold, with potential applications in light-emitting devices, chemical sensing, cell imaging and data storage, etc. The prospects of the relevant studies are also discussed.

Key words: aggregaion-induced emission, fluorine, cyclometalated complex, organometallic complex, phosphorescence

Cite this article

Chengyuan Qin, Jinling Miao, Yong Nie, Wei Liu, Ying Gao, Tianrui Li, Xuchuan Jiang. Advances in Fluorinated Organometallic Complexes with Aggregation-Induced Emission Characteristics[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 504-520.

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化合物	吸收峰^a/nm	发射峰^b/nm	发光量子效率^b/%	发光寿命	潜在应用	文献
1	—	563	53	—	—	[42]
2	—	596	24	—	—	[42]
3	254, 290, 330, 388, 437, 465	605	—	23 ns^a	OLED, 传感器	[43]
4	253, 290, 328, 388, 435, 465	597	—	22 ns^a, 67 ns^b	OLED, 传感器	[43]
6	259, 281, 327, 369, 388, 435, 465	597	—	22 ns^a, 56 ns^b	OLED, 传感器	[43]
7	268, 350, 430	441, 472, 506	5.41	—	—	[44]
8	255, 338, 369, 430	448, 476, 507	41.43	—	—	[44]
9	255, 339, 367, 419	443, 478, 507	10.65	—	—	[44]
10	262, 337, 369, 419	481	10.95	—	—	[44]
11	275, 371, 430	460, 493, 529	5.77	—	—	[44]
12	254, 307, 370, 469	461, 488	7.25	2.00 ns^b	Hg(II)传感器	[45]
13	253, 302, 371, 450	461, 488	6.62	3.38 ns^b	Hg(II)传感器	[45]
14	253, 302, 271, 450	461, 488	—	—	—	[45]
15	264, 297, 337, 406	505	11	9.4 μs ^b	探针、发光材料和数据保护	[46]
16	268, 298, 337, 458	569	12	9.7 μs ^b	探针、发光材料和数据保护	[46]
17	265, 298, 350, 406	511	28	—	潜在指纹检测	[47]
18	264, 297, 335, 487	660	20	7.07 ms^b	线粒体靶向探针	[48]
19	263, 296, 331, 347	593	12	5.72 ms^b	线粒体靶向探针	[48]
20	245, 351	550	7.4	—	TNT-磷光探针	[49]
21	266, 359	584	4.4	—	光动力疗法	[50]
22	374	544	6.8	4.24 μs ^b	线粒体靶向探针	[51]
23	—	452, 486	52	1.4 μs ^b (486 nm)	—	[52]
24	242, 309, 360	625	6	27.95 μs ^b	线粒体靶向探针	[53]
25	—	537	—	—	光学记录,压力感应	[54]
26	—	461	—	1.20 μs ^b	—	[55]
27	—	467	—	0.29 μs ^b	化学传感	[55]
28	—	512	—	1.38 μs ^b	—	[55]
29	—	—	23.6	—	—	[56]
30	249, 319, 357	612	31	0.18 μs ^a	光学记录	[57]
31	253, 322, 366	627	24	0.17 μs ^a	光学记录	[57]
32a	—	479	33.3	0.023 μs ^a,1.16 μs ^b	信息存储, 数据保护	[58]
32b	—	498	5.9	0.028 μs ^a, 1.20 μs ^b	信息存储, 数据保护	[58]
32c	—	516	8.4	0.038 μs ^a, 0.28 μs ^b	信息存储, 数据保护	[58]
33	607	529	75	0.67 μs ^b	传感, 数据记录	[59]
34	—	≈500	—	—	TNP检测	[60]
35	372, 402, 457	469, 500	11	1.82 μs ^b (500 nm)	防伪	[61]
36	355, 378, 459	470, 501	55	2.80 μs ^b (501 nm)	防伪	[61]
37	365, 384, 442	456, 486	57	4.15 μs ^b (486 nm)	防伪	[61]
38	360, 379, 443	452, 480	52	4.55 μs ^b (480 nm)	防伪	[61]
39	—	—	10.6	—	指纹检测	[62]
40	275, 330	716	12	1.93 μs ^b	OLED	[63]

化合物	吸收峰^a/nm	发射峰^b/nm	发光量子效率^b/%	发光寿命	潜在应用	文献
1	—	563	53	—	—	[42]
2	—	596	24	—	—	[42]
3	254, 290, 330, 388, 437, 465	605	—	23 ns^a	OLED, 传感器	[43]
4	253, 290, 328, 388, 435, 465	597	—	22 ns^a, 67 ns^b	OLED, 传感器	[43]
6	259, 281, 327, 369, 388, 435, 465	597	—	22 ns^a, 56 ns^b	OLED, 传感器	[43]
7	268, 350, 430	441, 472, 506	5.41	—	—	[44]
8	255, 338, 369, 430	448, 476, 507	41.43	—	—	[44]
9	255, 339, 367, 419	443, 478, 507	10.65	—	—	[44]
10	262, 337, 369, 419	481	10.95	—	—	[44]
11	275, 371, 430	460, 493, 529	5.77	—	—	[44]
12	254, 307, 370, 469	461, 488	7.25	2.00 ns^b	Hg(II)传感器	[45]
13	253, 302, 371, 450	461, 488	6.62	3.38 ns^b	Hg(II)传感器	[45]
14	253, 302, 271, 450	461, 488	—	—	—	[45]
15	264, 297, 337, 406	505	11	9.4 μs ^b	探针、发光材料和数据保护	[46]
16	268, 298, 337, 458	569	12	9.7 μs ^b	探针、发光材料和数据保护	[46]
17	265, 298, 350, 406	511	28	—	潜在指纹检测	[47]
18	264, 297, 335, 487	660	20	7.07 ms^b	线粒体靶向探针	[48]
19	263, 296, 331, 347	593	12	5.72 ms^b	线粒体靶向探针	[48]
20	245, 351	550	7.4	—	TNT-磷光探针	[49]
21	266, 359	584	4.4	—	光动力疗法	[50]
22	374	544	6.8	4.24 μs ^b	线粒体靶向探针	[51]
23	—	452, 486	52	1.4 μs ^b (486 nm)	—	[52]
24	242, 309, 360	625	6	27.95 μs ^b	线粒体靶向探针	[53]
25	—	537	—	—	光学记录,压力感应	[54]
26	—	461	—	1.20 μs ^b	—	[55]
27	—	467	—	0.29 μs ^b	化学传感	[55]
28	—	512	—	1.38 μs ^b	—	[55]
29	—	—	23.6	—	—	[56]
30	249, 319, 357	612	31	0.18 μs ^a	光学记录	[57]
31	253, 322, 366	627	24	0.17 μs ^a	光学记录	[57]
32a	—	479	33.3	0.023 μs ^a,1.16 μs ^b	信息存储, 数据保护	[58]
32b	—	498	5.9	0.028 μs ^a, 1.20 μs ^b	信息存储, 数据保护	[58]
32c	—	516	8.4	0.038 μs ^a, 0.28 μs ^b	信息存储, 数据保护	[58]
33	607	529	75	0.67 μs ^b	传感, 数据记录	[59]
34	—	≈500	—	—	TNP检测	[60]
35	372, 402, 457	469, 500	11	1.82 μs ^b (500 nm)	防伪	[61]
36	355, 378, 459	470, 501	55	2.80 μs ^b (501 nm)	防伪	[61]
37	365, 384, 442	456, 486	57	4.15 μs ^b (486 nm)	防伪	[61]
38	360, 379, 443	452, 480	52	4.55 μs ^b (480 nm)	防伪	[61]
39	—	—	10.6	—	指纹检测	[62]
40	275, 330	716	12	1.93 μs ^b	OLED	[63]

化合物	吸收峰^a/nm	发射峰^b/nm	发光量子效率^b/%	发光寿命^b	潜在应用	文献
41	261, 301, 321, 354, 386, 433	—	—	—	细胞成像	[65]
42	258, 321, 354, 383, 428	—	—	—	细胞成像	[65]
43	262, 325, 351, 386, 428	—	—	—	细胞成像	[65]
44	263, 306, 360, 396, 448	—	—	—	细胞成像	[65]
45	265, 286, 315, 330, 406	486, 518, 575	29	—	—	[66]
46a	281, 313, 343, 480	600	35	2.88 μs	—	[67]
46b	300, 320, 389, 465	521, 621	10	5.9 ns (521 nm) 488.51 ns (621 nm)	—	[67]
47	247, 275, 291, 304, 329, 353	480, 515, 585 (λ_ex: 400) 595 (λ_ex: 445~475) 506, 540, 580 (λ_ex: 400, 77 K)	—	13.2 μs (480 nm) 16.5 μs (515 nm) 157 μs (506 nm)	细胞成像	[68]
48a	252, 265, 282, 304, 347, 394, 465	565, 625 (λ_ex: 400~470) 520, 555 (λ_ex: 400, 77 K) 555, 605 (λ_ex: 440, 77 K)	—	11.1 μs (565 nm) 488 μs (625 nm) 41.7 μs (520 nm) 42.1 μs (555 nm) 47.9 μs (605 nm)	细胞成像	[68]
48b	236, 264, 255, 288, 306, 333, 356, 399	609 (λ_ex: 400~470) 510, 575, 610 (λ_ex: 380, 77 K) 555, 575, 610 (λ_ex: 440, 77 K)	—	12.8 μs (609 nm) 167 μs (510 nm) 112 μs (575 nm) 65.2 μs (610 nm)	细胞成像	[68]
48c	237, 252, 280, 302, 333, 362, 406	600 (λ_ex: 400~470) 481, 500, 523, 538 (λ_ex: 380, 77 K) 481, 500, 523, 538, 613 (λ_ex: 440, 77 K)	—	13.9 μs (600 nm) 76.6 μs (500 nm) 42.8 μs (613 nm)	细胞成像	[68]
49a	243, 261, 290, 309, 337, 370	496, 595 (λ_ex: 400) 595 (λ_ex: 450~480) 507, 544, 586 (λ_ex: 400, 77 K)	—	9.0 μs (495 nm) 14.5 μs (595 nm) 186 μs (507 nm)	细胞成像	[68]
49b	243, 261, 290, 309, 337, 370	545 (λ_ex: 400) 508, 532, 572 (λ_ex: 400, 77 K) 570 (λ_ex: 470)	—	9.1 μs (545 nm) 202.2 μs (532 nm) 20.1 μs (570 nm)	细胞成像	[68]
50	—	573	—	—	—	[69]
54	280, 360	600	65	404 ns	—	[71]
55	365, 420	495	—	—	—	[72]

化合物	吸收峰^a/nm	发射峰^b/nm	发光量子效率^b/%	发光寿命^b	潜在应用	文献
41	261, 301, 321, 354, 386, 433	—	—	—	细胞成像	[65]
42	258, 321, 354, 383, 428	—	—	—	细胞成像	[65]
43	262, 325, 351, 386, 428	—	—	—	细胞成像	[65]
44	263, 306, 360, 396, 448	—	—	—	细胞成像	[65]
45	265, 286, 315, 330, 406	486, 518, 575	29	—	—	[66]
46a	281, 313, 343, 480	600	35	2.88 μs	—	[67]
46b	300, 320, 389, 465	521, 621	10	5.9 ns (521 nm) 488.51 ns (621 nm)	—	[67]
47	247, 275, 291, 304, 329, 353	480, 515, 585 (λ_ex: 400) 595 (λ_ex: 445~475) 506, 540, 580 (λ_ex: 400, 77 K)	—	13.2 μs (480 nm) 16.5 μs (515 nm) 157 μs (506 nm)	细胞成像	[68]
48a	252, 265, 282, 304, 347, 394, 465	565, 625 (λ_ex: 400~470) 520, 555 (λ_ex: 400, 77 K) 555, 605 (λ_ex: 440, 77 K)	—	11.1 μs (565 nm) 488 μs (625 nm) 41.7 μs (520 nm) 42.1 μs (555 nm) 47.9 μs (605 nm)	细胞成像	[68]
48b	236, 264, 255, 288, 306, 333, 356, 399	609 (λ_ex: 400~470) 510, 575, 610 (λ_ex: 380, 77 K) 555, 575, 610 (λ_ex: 440, 77 K)	—	12.8 μs (609 nm) 167 μs (510 nm) 112 μs (575 nm) 65.2 μs (610 nm)	细胞成像	[68]
48c	237, 252, 280, 302, 333, 362, 406	600 (λ_ex: 400~470) 481, 500, 523, 538 (λ_ex: 380, 77 K) 481, 500, 523, 538, 613 (λ_ex: 440, 77 K)	—	13.9 μs (600 nm) 76.6 μs (500 nm) 42.8 μs (613 nm)	细胞成像	[68]
49a	243, 261, 290, 309, 337, 370	496, 595 (λ_ex: 400) 595 (λ_ex: 450~480) 507, 544, 586 (λ_ex: 400, 77 K)	—	9.0 μs (495 nm) 14.5 μs (595 nm) 186 μs (507 nm)	细胞成像	[68]
49b	243, 261, 290, 309, 337, 370	545 (λ_ex: 400) 508, 532, 572 (λ_ex: 400, 77 K) 570 (λ_ex: 470)	—	9.1 μs (545 nm) 202.2 μs (532 nm) 20.1 μs (570 nm)	细胞成像	[68]
50	—	573	—	—	—	[69]
54	280, 360	600	65	404 ns	—	[71]
55	365, 420	495	—	—	—	[72]

化合物	吸收峰^a/nm	发射峰^b/nm	发光量子效率^b/%	寿命^b	潜在应用	文献
56	—	407, 428	—	—	—	[74]
57 (n=2)	280, 328, 342	—	—	—	—	[75]
57 (n=5)	—	554, 596	—	—	—	[75]
60	—	467, 498	—	—	—	[76]
61a	—	513, 552	—	—	—	[77]
61b	—	530	—	—	—	[77]
62	336	462, 550, 598	22.5	86.84 ms (550 nm)	—	[78]
63	—	454	21.4	1.53 μs	—	[79]
64	—	453, 560	—	13.72 μs (560 nm)	—	[80]
65	—	526	—	30.79 μs	—	[80]
66	—	512	—	4.20 μs	—	[80]
67	254	556	3.7	—	—	[81]
68	255	557	6.3	—	—	[81]
69	239	419	27.7	—	—	[81]
70	306	627	—	—	—	[81]
71	238, 325	512, 551,596	—	—	—	[81]
72 (n=2)	—	485	—	0.77 μs	—	[82]
73	266, 280, 352	—	65.42	—	—	[83-84]
74	—	499	49.46	—	—	[84]
75	—	389, 501	5.42	—	—	[84]
76	304, 324, 338	490, 523	40.51	—	—	[85]
77	—	496	—	—	—	[86]
78	—	516	—	—	—	[86]
79	—	430	—	—	—	[87]
82	270	572^a	—	—	—	[88]
84 (n=5)	—	505, 540	5	18.37 μs (505 nm) 16.00 μs (540 nm)	自擦除复写纸柔性防伪无碳复印纸	[89]
84 (n=6)	—	500, 540	4	22.43 μs (500 nm) 22.72 μs (540 nm)		[89]
84 (n=7)	—	505, 540	4	15.97 μs (505 nm) 16.72 μs (540 nm)		[89]
84(n=8)	—	500, 535	68	201.68 μs (500 nm) 184.05 μs (535 nm)		[89]
84(n=9)	—	500, 535	64	206.00 μs (500 nm) 201.48 μs (535 nm)		[89]
84(n=10)	—	500, 535	16	127.47 μs (500 nm) 124.61 μs (535 nm)		[89]
85	—	470	—	—	生物传感	[90]
86(R,R)	—	504^a, 500	15	12 ms	—	[91]
86(S,S)	—	504^a, 500	16	8 ms	—	[91]
87	—	527	—	0.87 μs	—	[92]
88	—	500	15.1	—	—	[93]
89		498	8.1	—	—	[93]
90		498	8.3	—	—	[93]
91	—	389	5.8	—	—	[84]
92	—	376, 452, 471	10.63	—	—	[84]

具有聚集诱导发光特性的含氟有机金属配合物的研究进展

Advances in Fluorinated Organometallic Complexes with Aggregation-Induced Emission Characteristics

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化合物	吸收峰^a/nm	发射峰^b/nm	发光量子效率^b/%	发光寿命^b/ns	潜在应用	文献
93	337, 365	565	9.3	13.7	—	[94]
94	337, 366	566	8.6	4.3	—	[94]
95	369	486	—		化学传感	[95]
96	365	485	—		—	[95]
97	369	493	—		化学传感	[95]

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