Citation: Wang Xuan, Gan Nan, Gu Mingxing, Ling Kun, Ma Chaoqun, Ma Huili, Yao Wei, Zhang Yujian, Shi Huifang, An Zhongfu, Huang Wei. Subtle structure tailoring of metal-free triazine luminogens for highly efficient ultralong organic phosphorescence[J]. Chinese Chemical Letters, ;2019, 30(11): 1935-1938. doi: 10.1016/j.cclet.2018.12.023 shu

Subtle structure tailoring of metal-free triazine luminogens for highly efficient ultralong organic phosphorescence

Wang Xuan ^a,1 ,
Gan Nan ^a,1 ,
Gu Mingxing ^a ,
Ling Kun ^a ,
Ma Chaoqun ^a ,
Ma Huili ^a ,
Yao Wei ^a ,
Zhang Yujian ^b ,
Shi Huifang ^a,*, ,
An Zhongfu ^a,*, ,
Huang Wei ^a,c,*,

a.
Key Laboratory of Flexible Electronics(KLOFE) & Institute of Advanced Materials(IAM), Jiangsu National Synergistic Innovation Center for Advanced Materials(SICAM), Nanjing Tech University(Nanjing Tech), Nanjing 211816, China
b.
Department of Materials Chemistry, Huzhou University, Huzhou 313000, China
c.
Shanxi Institute of Flexible Electronics(SIFE), Northwestern Polytechnical University(NPU), Xi'an 710072, China

iamhfshi@njtech.edu.cn

iamzfan@njtech.edu.cn

wei-huang@njtech.edu.cn

Received Date: 10 November 2018
Revised Date: 17 December 2018
Accepted Date: 18 December 2018
Available Online: 19 November 2018

Figures(4)

Ultralong organic phosphorescent materials have invoked considerable attention for their great potential in sensing, data encryption, information anti-counterfeiting and so forth. However, effective ways to achieve highly efficient ultralong organic phosphorescence (UOP) in metal-free organic materials remain a great challenge. Herein, we designed three isomers based on asymmetric triazines with various bromine substituted positions. Impressively, phosphorescence efficiency of p-BrAT in solid state can reach up to 9.7% with a long lifetime of 386 ms, which was one of the highest efficient UOP materials reported so far. Theoretical calculations further demonstrated that para-substitution exhibited the most effective radiative transition for triplet excitons. These results will provide an effective approach to achieving highly efficient UOP materials.
- Ultralong organic phosphorescence (UOP),
- Isomerism,
- Crystal engineering,
- H-aggregation,
- Intermolecular interactions
1. [1]
  R. Kabe, N. Notsuka, K. Yoshida, C. Adachi, Adv. Mater. 28(2016) 655-660. doi: 10.1002/adma.201504321
2. [2]
  X. Zhen, Y. Tao, Z. An, et al., Adv. Mater. 29(2017) 1606665. doi: 10.1002/adma.201606665
3. [3]
  S.M.A. Fateminia, Z. Mao, S. Xu, et al., Angew. Chem. Int. Ed. 56(2017) 12160-12164. doi: 10.1002/anie.201705945
4. [4]
  L. Gu, H. Shi, M. Gu, et al., Angew. Chem. Int. Ed. 57(2018) 8425-8431. doi: 10.1002/anie.201712381
5. [5]
  Z. Yu, Y. Wu, L. Xiao, et al., J. Am. Chem. Soc. 139(2017) 6376-6381. doi: 10.1021/jacs.7b01574
6. [6]
  K. Li, L. Zhao, Y. Gong, et al., Sci. China Chem. 60(2017) 806-812. doi: 10.1007/s11426-016-0460-8
7. [7]
  Y. Yang, K.Z. Wang, D. Yan, ACS Appl. Mater. Interfaces 9(2017) 17399-17407. doi: 10.1021/acsami.7b00594
8. [8]
  Q. Wu, H. Ma, K. Ling, et al., ACS Appl. Mater. Interfaces 10(2018) 33730-33736. doi: 10.1021/acsami.8b13713
9. [9]
  L. Huang, B. Chen, X. Zhang, et al., Angew. Chem. Int. Ed. 57(2018) 16046-16050. doi: 10.1002/anie.201808861
10. [10]
  H. Xu, R. Chen, Q. Sun, et al., Chem. Soc. Rev. 43(2014) 3259-3302. doi: 10.1039/C3CS60449G
11. [11]
  Z. Pan, Y. Lu, F. Liu, Chem. Soc. Rev. 46(2017) 275-299. doi: 10.1039/C6CS00551A
12. [12]
  E.M. Schulman, R.T. Parker, J. Phys. Chem. 81(1977) 1932-1939. doi: 10.1021/j100535a010
13. [13]
  M.A. El-Sayed, Acc. Chem. Res. 1(1968) 8-16. doi: 10.1021/ar50001a002
14. [14]
  Y. Xie, Y. Ge, Q. Peng, et al., Adv. Mater. 29(2017) 1606829. doi: 10.1002/adma.201606829
15. [15]
  Y. Xiong, Z. Zhao, W. Zhao, et al., Angew. Chem. Int. Ed. 57(2018) 7997-8001. doi: 10.1002/anie.201800834
16. [16]
  O. Bolton, K. Lee, H.J. Kim, et al., Nat. Chem. 3(2011) 205. doi: 10.1038/nchem.984
17. [17]
  H. Ma, W. Shi, J. Ren, et al., J. Phys. Chem. Lett. 7(2016) 2893-2898. doi: 10.1021/acs.jpclett.6b01156
18. [18]
  S. Kuila, K.V. Rao, S. Garain, et al., Angew. Chem. Int. Ed. 57(2018) 17115-17119. doi: 10.1002/anie.201810823
19. [19]
  Z. An, C. Zheng, Y. Tao, et al., Nat. Mater. 14(2015) 685-690. doi: 10.1038/nmat4259
20. [20]
  E. Lucenti, A. Forni, C. Botta, et al., J. Phys. Chem. Lett. 8(2017) 1894-1898. doi: 10.1021/acs.jpclett.7b00503
21. [21]
  S. Cai, H. Shi, J. Li, et al., Adv. Mater. 29(2017) 1701244. doi: 10.1002/adma.201701244
22. [22]
  S. Hirata, K. Totani, J. Zhang, et al., Adv. Funct. Mater. 23(2013) 3386-3397. doi: 10.1002/adfm.201203706
23. [23]
  C. Xu, L. Xu, X. Ma, Chin. Chem. Lett. 29(2018) 970-972. doi: 10.1016/j.cclet.2017.11.045
24. [24]
  T. Ogoshi, H. Tsuchida, T. Kakuta, et al., Adv. Funct. Mater. 28(2018) 1707369. doi: 10.1002/adfm.201707369
25. [25]
  S. Hirata, M. Vacha, J. Phys. Chem. Lett. 7(2016) 1539-1545. doi: 10.1021/acs.jpclett.6b00554
26. [26]
  D. Li, F. Lu, J. Wang, et al., J. Am. Chem. Soc. 140(2018) 1916-1923. doi: 10.1021/jacs.7b12800
27. [27]
  J. Yang, X. Zhen, B. Wang, et al., Nat. Commun. 9(2018) 840-850. doi: 10.1038/s41467-018-03236-6
28. [28]
  Z. Cheng, H. Shi, H. Ma, et al., Angew. Chem. Int. Ed. 57(2018) 678-682. doi: 10.1002/anie.201710017
29. [29]
  C. Sun, X. Ran, X. Wang, et al., J. Phys. Chem. Lett. 9(2018) 335-339. doi: 10.1021/acs.jpclett.7b02953
30. [30]
  C.R. Wang, Y.Y. Gong, W.Z. Yuan, Y.M. Zhang, Chin. Chem. Lett. 27(2016) 1184-1192. doi: 10.1016/j.cclet.2016.05.026
31. [31]
  W. Luo, Y. Zhang, Y. Gong, et al., Chin. Chem. Lett. 29(2018) 1533-1536. doi: 10.1016/j.cclet.2018.08.001
32. [32]
  W. Zhao, Z. He, J.W.Y. Lam, et al., Chem 1(2016) 592-602. doi: 10.1016/j.chempr.2016.08.010
33. [33]
  J. Wei, B. Liang, R. Duan, Angew. Chem. Int. Ed. 55(2016) 15589-15593. doi: 10.1002/anie.201607653
34. [34]
  G. Chen, H. Feng, F. Feng, et al., J. Phys. Chem. Lett. 9(2018) 6305-6311. doi: 10.1021/acs.jpclett.8b02742
35. [35]
  B. Zhou, D. Yan, Adv. Funct. Mater. 29(2019) 1807599. doi: 10.1002/adfm.201807599
36. [36]
  H. Liu, Z. Bian, Q. Cheng, et al., Chem. Sci. 10(2019) 227-232. doi: 10.1039/C8SC03135E
37. [37]
  X. Yang, D. Yan, Chem. Sci. 7(2016) 4519-4526. doi: 10.1039/C6SC00563B
38. [38]
  H. Mieno, R. Kabe, N. Notsuka, Adv. Optical Mater. 4(2016) 1015-1021. doi: 10.1002/adom.201600103
39. [39]
  X. Yang, D. Yan, Adv. Optical Mater. 4(2016) 897-905. doi: 10.1002/adom.201500666
40. [40]
  S. Cai, H. Shi, Z. Zhang, et al., Angew. Chem. Int. Ed. 57(2018) 4005-4009. doi: 10.1002/anie.201800697
41. [41]
  X. Chen, C. Xu, T. Wang, et al., Angew. Chem. Int. Ed. 55(2016) 9872-9876. doi: 10.1002/anie.201601252
42. [42]
  W. Shi, J. Yao, L. Bai, et al., Adv. Funct. Mater. 28(2018) 1804961. doi: 10.1002/adfm.201804961
43. [43]
  Y. Su, S.Z.F. Phua, et al., Sci. Adv. 4(2018) EAAS9732. doi: 10.1126/sciadv.aas9732
44. [44]
  T. Ogoshi, H. Tsuchida, T. Kakuta, et al., Adv. Funct. Mater. 28(2018)1707369. doi: 10.1002/adfm.201707369
45. [45]
  N. Gan, H. Shi, Z. An, et al., Adv. Funct. Mater. 28(2018) 1802657. doi: 10.1002/adfm.201802657
46. [46]
  Y. Gong, G. Chen, Q. Peng, et al., Adv. Mater. 27(2015) 6195-6201. doi: 10.1002/adma.201502442
47. [47]
  S. Xu, R. Chen, C. Zheng, et al., Adv. Mater. 28(2016) 9920-9940. doi: 10.1002/adma.201602604
48. [48]
  Z. Shuai, Q. Peng, Phys. Rep. 537(2014) 123. doi: 10.1016/j.physrep.2013.12.002
49. [49]
  M. Jia, Z. Zhou, M. Lv, et al., Chin. Chem. Lett. 29(2018) 543-546. doi: 10.1016/j.cclet.2017.09.022
50. [50]
  E. Lee, S. Gwon, Y. Son, et al., Chin. Chem. Lett. 23(2012) 484-487. doi: 10.1016/j.cclet.2012.01.020
51. [51]
  Z. Sun, S. Li, Z. Liu, et al., Chin. Chem. Lett. 27(2016) 1131-1138. doi: 10.1016/j.cclet.2016.06.007
52. [52]
  Y. Liu, G. Zhan, Z. Liu, et al., Chin. Chem. Lett. 27(2016) 1231-1240. doi: 10.1016/j.cclet.2016.06.029
53. [53]
  H. Wua, B. Wu, X. Yu, et al., Chin. Chem. Lett. 28(2017) 2151-2154. doi: 10.1016/j.cclet.2017.08.002
54. [54]
  S. Cai, H. Shi, D. Tian, et al., Adv. Funct. Mater. 28(2018) 1705045. doi: 10.1002/adfm.201705045
55. [55]
  P. Xue, P. Wang, P. Chen, et al., Chem. Sci. 8(2017) 6060-6065. doi: 10.1039/C5SC03739E
56. [56]
  Z. Yang, Z. Mao, X. Zhang, et al., Angew. Chem. Int. Ed. 55(2016) 2181-2185. doi: 10.1002/anie.201509224
57. [57]
  L. Bian, H. Shi, X. Wang, et al., J. Am. Chem. Soc. 140(2018) 10734-10739. doi: 10.1021/jacs.8b03867
58. [58]
  X. Ma, C. Xu, J. Wang, et al., Angew. Chem. Int. Ed. 57(2018) 10854-10858. doi: 10.1002/anie.201803947
1. [1]
  Na Wang , Wang Luo , Huaiyi Shen , Huakai Li , Zejiang Xu , Zhiyuan Yue , Chao Shi , Hengyun Ye , Leping Miao . Crystal engineering regulation achieving inverse temperature symmetry breaking ferroelasticity in a cationic displacement type hybrid perovskite system. Chinese Chemical Letters, 2024, 35(5): 108696-. doi: 10.1016/j.cclet.2023.108696
2. [2]
  Hao-Fei Ni , Jia-He Lin , Gele Teri , Qiang-Qiang Jia , Pei-Zhi Huang , Hai-Feng Lu , Chang-Feng Wang , Zhi-Xu Zhang , Da-Wei Fu , Yi Zhang . B-site ion regulation strategy enables performance optimization and multifunctional integration of hybrid perovskite ferroelectrics. Chinese Chemical Letters, 2025, 36(3): 109690-. doi: 10.1016/j.cclet.2024.109690
3. [3]
  Jiarui Wu , Gengxin Wu , Yan Wang , Yingwei Yang . Crystal Engineering Based on Leaning Towerarenes. University Chemistry, 2024, 39(3): 58-62. doi: 10.3866/PKU.DXHX202304014
4. [4]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
5. [5]
  Jiakun Bai , Junhui Jia , Aisen Li . An elastic organic crystal with piezochromic luminescent behavior. Chinese Journal of Structural Chemistry, 2024, 43(6): 100323-100323. doi: 10.1016/j.cjsc.2024.100323
6. [6]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
7. [7]
  Pu Zhang , Xiang Mao , Xuehua Dong , Ling Huang , Liling Cao , Daojiang Gao , Guohong Zou . Two UV organic-inorganic hybrid antimony-based materials with superior optical performance derived from cation-anion synergetic interactions. Chinese Chemical Letters, 2024, 35(9): 109235-. doi: 10.1016/j.cclet.2023.109235
8. [8]
  Xianxu Chu , Lu Wang , Junru Li , Hui Xu . Surface chemical microenvironment engineering of catalysts by organic molecules for boosting electrocatalytic reaction. Chinese Chemical Letters, 2024, 35(8): 109105-. doi: 10.1016/j.cclet.2023.109105
9. [9]
  Min Chen , Boyu Peng , Xuyun Guo , Ye Zhu , Hanying Li . Polyethylene interfacial dielectric layer for organic semiconductor single crystal based field-effect transistors. Chinese Chemical Letters, 2024, 35(4): 109051-. doi: 10.1016/j.cclet.2023.109051
10. [10]
  Yuqing Ding , Zhiying Yi , Zhihui Wang , Hongyu Chen , Yan Zhao . Liquid nitrogen post-treatment for improved aggregation and electrical properties in organic semiconductors. Chinese Chemical Letters, 2024, 35(12): 109918-. doi: 10.1016/j.cclet.2024.109918
11. [11]
  Tengjia Ni , Xianbiao Hou , Huanlei Wang , Lei Chu , Shuixing Dai , Minghua Huang . Controllable defect engineering based on cobalt metal-organic framework for boosting oxygen evolution reaction. Chinese Journal of Structural Chemistry, 2024, 43(1): 100210-100210. doi: 10.1016/j.cjsc.2023.100210
12. [12]
  Zhenchun Yang , Bixiao Guo , Zhenyu Hu , Kun Wang , Jiahao Cui , Lina Li , Chun Hu , Yubao Zhao . Molecular engineering towards dual surface local polarization sites on poly(heptazine imide) framework for boosting H₂O₂ photo-production. Chinese Chemical Letters, 2024, 35(8): 109251-. doi: 10.1016/j.cclet.2023.109251
13. [13]
  Jiayin Zhou , Depeng Liu , Longqiang Li , Min Qi , Guangqiang Yin , Tao Chen . Responsive organic room-temperature phosphorescence materials for spatial-time-resolved anti-counterfeiting. Chinese Chemical Letters, 2024, 35(11): 109929-. doi: 10.1016/j.cclet.2024.109929
14. [14]
  Chong-Yang Shi , Jian-Xing Gong , Zhen Li , Chao Shu , Long-Wu Ye , Qing Sun , Bo Zhou , Xin-Qi Zhu . Gold-catalyzed intermolecular amination of allyl azides with ynamides: Efficient construction of 3-azabicyclo[3.1.0] scaffold. Chinese Chemical Letters, 2025, 36(2): 109895-. doi: 10.1016/j.cclet.2024.109895
15. [15]
  Weihong Ding , Kaiyue Song , Xianglong Li , Xiaoxia Sun . High-temperature-stable RRAMs with well-defined thermal effect mechanisms enable by engineering of robust 2D <100>-oriented organic-inorganic hybrid perovskites. Chinese Chemical Letters, 2025, 36(4): 110495-. doi: 10.1016/j.cclet.2024.110495
16. [16]
  Songtao Cai , Liuying Wu , Yuan Li , Soham Samanta , Jinying Wang , Bing Liu , Feihu Wu , Kaitao Lai , Yingchao Liu , Junle Qu , Zhigang Yang . Intermolecular hydrogen-bonding as a robust tool toward significantly improving the photothermal conversion efficiency of a NIR-II squaraine dye. Chinese Chemical Letters, 2024, 35(4): 108599-. doi: 10.1016/j.cclet.2023.108599
17. [17]
  Fengyao Cui , Qiaona Zhang , Tangxin Xiao , Zhouyu Wang , Leyong Wang . Reversible phosphorescence in pseudopolyrotaxane elastomer. Chinese Chemical Letters, 2024, 35(10): 110061-. doi: 10.1016/j.cclet.2024.110061
18. [18]
  Bicheng Zhu , Jingsan Xu . S-scheme heterojunction photocatalyst for H2 evolution coupled with organic oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100327-100327. doi: 10.1016/j.cjsc.2024.100327
19. [19]
  Zhenzhu Wang , Chenglong Liu , Yunpeng Ge , Wencan Li , Chenyang Zhang , Bing Yang , Shizhong Mao , Zeyuan Dong . Differentiated self-assembly through orthogonal noncovalent interactions towards the synthesis of two-dimensional woven supramolecular polymers. Chinese Chemical Letters, 2024, 35(5): 109127-. doi: 10.1016/j.cclet.2023.109127
20. [20]
  Bingbing Shi , Yuchun Wang , Yi Zhou , Xing-Xing Zhao , Yizhou Li , Nuoqian Yan , Wen-Juan Qu , Qi Lin , Tai-Bao Wei . A supramolecular oligo[2]rotaxane constructed by orthogonal platinum(Ⅱ) metallacycle and pillar[5]arene-based host–guest interactions. Chinese Chemical Letters, 2024, 35(10): 109540-. doi: 10.1016/j.cclet.2024.109540

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(720)
HTML views(24)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142