Citation: Kuofei Li, Tao Wang, Bing Yao, Yuannan Chen, Hao Deng, Hongmei Zhan, Zhiyuan Xie, Yanxiang Cheng. Carbazole ring: A delicate rack for constructing thermally activated delayed fluorescent compounds with through-space charge transfer[J]. Chinese Chemical Letters, ;2021, 32(12): 4011-4014. doi: 10.1016/j.cclet.2021.05.054 shu

Carbazole ring: A delicate rack for constructing thermally activated delayed fluorescent compounds with through-space charge transfer

Kuofei Li ^{a, b} ,
Tao Wang ^a ,
Bing Yao ^a ,
Yuannan Chen ^a ,
Hao Deng ^{a, b} ,
Hongmei Zhan ^{a, *,} ,
Zhiyuan Xie ^a ,
Yanxiang Cheng ^{a, b, *,}

a.
State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
b.
School of Applied Chemistry and Engineering, University of Science and Technology of China, Hefei 230026, China

hmzhan@ciac.ac.cn

yanxiang@ciac.ac.cn

Received Date: 7 February 2021
Revised Date: 23 May 2021
Accepted Date: 24 May 2021
Available Online: 31 May 2021

Figures(4)

Three carbazole derivatives, AcPTC, PxPTC and PtPTC, consisting of two 9,9-dimethyl-9,10-dihydroacridine, phenoxazine or phenothiazine donor groups and one diphenyltriazine acceptor group fixed at 1,8,9-positions of a single carbazole ring via phenylene, are designed and synthesized. X-ray diffraction analysis of AcPTC reveals that there exist multiple π-π interactions between the donor and acceptor groups to form a sandwich-like structural unit with edge-to-face interaction model. The compounds thus show obvious thermally activated delayed fluorescence with through-space charge transfer character and possess considerable photoluminescence quantum yields of up to 73% in doped films with sky-blue to yellow emissions. The solution-processed electroluminescent devices achieve the highest maximum external quantum efficiencies of 10.0%, 11% and 5.6% for AcPTC, PxPTC and PtPTC, respectively, with small efficiency roll-offs.
- Thermally activated delayed fluorescence,
- Through-space charge transfer,
- Carbazole,
- Solution-processed devices,
- Sky-blue emission
1. [1]
  Q. Wei, N. Fei, A. Islam, et al., Adv. Opt. Mater. 6 (2018) 1800512. doi: 10.1002/adom.201800512
2. [2]
  T.J. Penfold, F.B. Dias, A.P. Monkman, Chem. Commun. 54 (2018) 3926-3935. doi: 10.1039/C7CC09612G
3. [3]
  X. Tian, H. Sun, Q. Zhang, C. Adachi, Chin. Chem. Lett. 27 (2016) 1445-1452. doi: 10.1016/j.cclet.2016.07.017
4. [4]
  Z. Yang, Z. Mao, Z. Xie, et al., Chem. Soc. Rev. 46 (2017) 915-1016. doi: 10.1039/C6CS00368K
5. [5]
  Y. Im, M. Kim, Y.J. Cho, et al., Chem. Mater. 29 (2017) 1946-1963. doi: 10.1021/acs.chemmater.6b05324
6. [6]
  S. Xu, Q. Yang, Y. Zhang, et al., Chin. Chem. Lett. 32 (2021) 1372-1376. doi: 10.1016/j.cclet.2020.10.022
7. [7]
  M.Y. Wong, E. Zysman-Colman, Adv. Mater. 29 (2017) 1605444. doi: 10.1002/adma.201605444
8. [8]
  W. Yuan, H. Yang, M. Zhang, et al., Chin. Chem. Lett. 30 (2019) 1955-1958. doi: 10.1016/j.cclet.2019.08.019
9. [9]
  H. Tsujimoto, D.G. Ha, G. Markopoulos, et al., J. Am. Chem. Soc. 139 (2017) 4894-4900. doi: 10.1021/jacs.7b00873
10. [10]
  S. Shao, J. Hu, X. Wang, et al., J. Am. Chem. Soc. 139 (2017) 17739-17742. doi: 10.1021/jacs.7b10257
11. [11]
  H. Li, X. Tang, S. Yang, et al., Chin. Chem. Lett. 32 (2021) 1245-1248. doi: 10.1016/j.cclet.2020.08.045
12. [12]
  J. Li, P. Shen, Z. Zhao, B.Z. Tang, et al., CCS Chem 1 (2019) 181-196.
13. [13]
  C. Peng, S. Yang, H. Li, et al., Adv. Mater. 32 (2020) 2003885. doi: 10.1002/adma.202003885
14. [14]
  B. Wex, B.R. Kaafarani, J. Mater. Chem. C 5 (2017) 8622-8653. doi: 10.1039/C7TC02156A
15. [15]
  Z. Ma, Y. Wan, W. Dong, et al., Chin. Chem. Lett. 32 (2021) 703-707. doi: 10.1016/j.cclet.2020.06.025
16. [16]
  Q. Li, J. Hu, J. Lv, et al., Angew. Chem. Int. Ed. 59 (2020) 20174-20182. doi: 10.1002/anie.202008912
17. [17]
  Z. Wei, K. Zhang, C.K. Kim, et al., Chin. Chem. Lett. 32 (2021) 493-496. doi: 10.1016/j.cclet.2020.05.005
18. [18]
  D. Zhou, C.H. Ryoo, D. Liu, et al., Adv. Opt. Mat. 8 (2020) 1901021. doi: 10.1002/adom.201901021
19. [19]
  K. Li, Y. Zhu, B. Yao, et al., Chem. Commun. 56 (2020) 5957-5960. doi: 10.1039/D0CC01738H
20. [20]
  J.A. Lin, S.W. Li, Z.Y. Liu, et al., Chem. Mater. 31 (2019) 5981-5992. doi: 10.1021/acs.chemmater.9b02712
21. [21]
  K. Woon, C. Yi, K. Pan, M.K. Etherington, et al., J. Phys. Chem. C 123 (2019) 12400-12410. doi: 10.1021/acs.jpcc.9b01900
22. [22]
  X. Wang, S. Wang, J. Lv, et al., Chem. Sci. 10 (2019) 2915-2923. doi: 10.1039/C8SC04991B
23. [23]
  X. Tang, L.S. Cui, H.C. Li, et al., Nat. Mater. 19 (2020) 1332-1338. doi: 10.1038/s41563-020-0710-z
24. [24]
  C. Lefebvre, G. Rubez, H. Khartabil, et al., Phys. Chem. Chem. Phys. 19 (2017) 17928-17936. doi: 10.1039/C7CP02110K
25. [25]
  E.R. Johnson, S. Keinan, P. Mori-Sánchez, et al., J. Am. Chem. Soc. 132 (2010) 6498-6506. doi: 10.1021/ja100936w
26. [26]
  Y. Wada, H. Nakagawa, S. Matsumoto, Y. Wakisaka, H. Kaji, Nat. Photon. 14 (2020) 643-649. doi: 10.1038/s41566-020-0667-0
27. [27]
  M. Auffray, D.H. Kim, J.U. Kim, et al., Chem. Asian J. 14 (2019) 1921-1925. doi: 10.1002/asia.201900401
28. [28]
  C. Wu, W. Liu, K. Li, et al., Angew. Chem. Int. Ed. (2020), doi: 10.1002/anie.202013051. doi: 10.1002/anie.202013051
29. [29]
  P. Rajamalli, N. Senthilkumar, P. Gandeepan, et al., J. Am. Chem. Soc. 138 (2016) 628-634. doi: 10.1021/jacs.5b10950
1. [1]
  Xiao Yu , Dongyue Cui , Mengmeng Wang , Zhaojin Wang , Mengzhu Wang , Deshuang Tu , Vladimir Bregadze , Changsheng Lu , Qiang Zhao , Runfeng Chen , Hong Yan . Boron cluster-based TADF emitter via through-space charge transfer enabling efficient orange-red electroluminescence. Chinese Chemical Letters, 2025, 36(3): 110520-. doi: 10.1016/j.cclet.2024.110520
2. [2]
  Jun-Yi Wang , Jue-Yu Bao , Zheng-Guang Wu , Zheng-Yin Du , Xunwen Xiao , Xu-Feng Luo . Recent progress in steric modulation of MR-TADF materials and doping concentration independent OLEDs with narrowband emission. Chinese Journal of Structural Chemistry, 2025, 44(1): 100451-100451. doi: 10.1016/j.cjsc.2024.100451
3. [3]
  Xiangan Song , Shaogang Shen , Mengyao Lu , Ying Wang , Yong Zhang . Trifluoromethyl enable high-performance single-emitter white organic light-emitting devices based on quinazoline acceptor. Chinese Chemical Letters, 2024, 35(4): 109118-. doi: 10.1016/j.cclet.2023.109118
4. [4]
  Shunyu Wang , Yanan Zhu , Yang Zhao , Wanli Nie , Hong Meng . Steric effects and electronic manipulation of multiple donors on S₀/S₁ transition of D_n-A emitters. Chinese Chemical Letters, 2025, 36(4): 110555-. doi: 10.1016/j.cclet.2024.110555
5. [5]
  Zheng Zhao , Ben Zhong Tang . An efficient strategy enabling solution processable thermally activated delayed fluorescence emitter with high horizontal dipole orientation. Chinese Journal of Structural Chemistry, 2024, 43(6): 100270-100270. doi: 10.1016/j.cjsc.2024.100270
6. [6]
  Fuzheng Zhang , Chao Shi , Jiale Li , Fulin Jia , Xinyu Liu , Feiyang Li , Xinyu Bai , Qiuxia Li , Aihua Yuan , Guohua Xie . B-embedded narrowband pure near-infrared (NIR) phosphorescent iridium(Ⅲ) complexes and solution-processed OLED application. Chinese Chemical Letters, 2025, 36(1): 109596-. doi: 10.1016/j.cclet.2024.109596
7. [7]
  Haowen Shang , Yujie Yang , Bingjie Xue , Yikai Wang , Zhiyi Su , Wenlong Liu , Youzhi Wu , Xinjun Xu . Efficient solution-processed near-infrared organic light-emitting diodes with a binary-mixed electron transport layer. Chinese Chemical Letters, 2025, 36(4): 110511-. doi: 10.1016/j.cclet.2024.110511
8. [8]
  Liangji Chen , Zhen Yuan , Fudong Feng , Xin Zhou , Zhile Xiong , Wuji Wei , Hao Zhang , Banglin Chen , Shengchang Xiang , Zhangjing Zhang . A hydrogen-bonded organic framework containing fluorescent carbazole and responsive pyridyl units for sensing organic acids. Chinese Chemical Letters, 2024, 35(9): 109344-. doi: 10.1016/j.cclet.2023.109344
9. [9]
  Hui Liu , Xiangyang Tang , Zhuang Cheng , Yin Hu , Yan Yan , Yangze Xu , Zihan Su , Futong Liu , Ping Lu . Constructing multifunctional deep-blue emitters with weak charge transfer excited state for high-performance non-doped blue OLEDs and single-emissive-layer hybrid white OLEDs. Chinese Chemical Letters, 2024, 35(10): 109809-. doi: 10.1016/j.cclet.2024.109809
10. [10]
  Liwen Wang , Boyang Wang , Siyu Lu , Shubo Lv , Xiaoli Qu . High quantum yield yellow emission carbon dots for the construction of blue light blocking films. Chinese Chemical Letters, 2025, 36(2): 110497-. doi: 10.1016/j.cclet.2024.110497
11. [11]
  Chaoqun Ma , Yuebo Wang , Ning Han , Rongzhen Zhang , Hui Liu , Xiaofeng Sun , Lingbao Xing . Carbon dot-based artificial light-harvesting systems with sequential energy transfer and white light emission for photocatalysis. Chinese Chemical Letters, 2024, 35(4): 108632-. doi: 10.1016/j.cclet.2023.108632
12. [12]
  Rui Cheng , Xin Huang , Tingting Zhang , Jiazhuang Guo , Jian Yu , Su Chen . Solid superacid catalysts promote high-performance carbon dots with narrow-band fluorescence emission for luminescence solar concentrators. Chinese Chemical Letters, 2024, 35(8): 109278-. doi: 10.1016/j.cclet.2023.109278
13. [13]
  Yihu Ke , Shuai Wang , Fei Jin , Guangbo Liu , Zhiliang Jin , Noritatsu Tsubaki . Charge transfer optimization: Role of Cu-graphdiyne/NiCoMoO4 S-scheme heterojunction and Ohmic junction. Chinese Journal of Structural Chemistry, 2024, 43(12): 100458-100458. doi: 10.1016/j.cjsc.2024.100458
14. [14]
  Shuai Qiu , Jia He , Xiao Hu , Hongxia Yan , Zhao Gao , Wei Tian . Cation-π enhanced triplet-to-singlet Förster resonance energy transfer for fluorescence afterglow. Chinese Chemical Letters, 2025, 36(4): 110057-. doi: 10.1016/j.cclet.2024.110057
15. [15]
  Jieqiong Xu , Wenbin Chen , Shengkai Li , Qian Chen , Tao Wang , Yadong Shi , Shengyong Deng , Mingde Li , Peifa Wei , Zhuo Chen . Organic stoichiometric cocrystals with a subtle balance of charge-transfer degree and molecular stacking towards high-efficiency NIR photothermal conversion. Chinese Chemical Letters, 2024, 35(10): 109808-. doi: 10.1016/j.cclet.2024.109808
16. [16]
  Zhaorui Song , Qiulian Hao , Bing Li , Yuwei Yuan , Shanshan Zhang , Yongkuan Suo , Hai-Hao Han , Zhen Cheng . NIR-Ⅱ fluorescence lateral flow immunosensor based on efficient energy transfer probe for point-of-care testing of tumor biomarkers. Chinese Chemical Letters, 2025, 36(1): 109834-. doi: 10.1016/j.cclet.2024.109834
17. [17]
  Quanyou Guo , Yue Yang , Tingting Hu , Hongqi Chu , Lijun Liao , Xuepeng Wang , Zhenzi Li , Liping Guo , Wei Zhou . Regulating local electron transfer environment of covalent triazine frameworks through F, N co-modification towards optimized oxygen reduction reaction. Chinese Chemical Letters, 2025, 36(1): 110235-. doi: 10.1016/j.cclet.2024.110235
18. [18]
  Hui Peng , Xiao Wang , Weiguo Huang , Shuiyue Yu , Linghang Kong , Qilin Wei , Jialong Zhao , Bingsuo Zou . Efficient tunable visible and near-infrared emission in Sb³⁺/Sm³⁺-codoped Cs₂NaLuCl₆ for near-infrared light-emitting diode, triple-mode fluorescence anti-counterfeiting and information encryption. Chinese Chemical Letters, 2024, 35(11): 109462-. doi: 10.1016/j.cclet.2023.109462
19. [19]
  Huizhong Wu , Ruiheng Liang , Ge Song , Zhongzheng Hu , Xuyang Zhang , Minghua Zhou . Enhanced interfacial charge transfer on Bi metal@defective Bi₂Sn₂O₇ quantum dots towards improved full-spectrum photocatalysis: A combined experimental and theoretical investigation. Chinese Chemical Letters, 2024, 35(6): 109131-. doi: 10.1016/j.cclet.2023.109131
20. [20]
  Ying Hou , Zhen Liu , Xiaoyan Liu , Zhiwei Sun , Zenan Wang , Hong Liu , Weijia Zhou . Laser constructed vacancy-rich TiO_2-x/Ti microfiber via enhanced interfacial charge transfer for operando extraction-SERS sensing. Chinese Chemical Letters, 2024, 35(9): 109634-. doi: 10.1016/j.cclet.2024.109634

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(599)
HTML views(51)

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