Citation: HUANG Bin, DAI Yu, BAN Xin-Xin, JIANG Wei, ZHANG Zhao-Hang, SUN Kai-Yong, LIN Bao-Ping, SUN Yue-Ming. Thermally Activated Delayed Fluorescence Materials Based on Triphenylamine/Diphenyl Sulfone[J]. Acta Physico-Chimica Sinica, ;2015, 31(8): 1621-1628. doi: 10.3866/PKU.WHXB201506121 shu

Thermally Activated Delayed Fluorescence Materials Based on Triphenylamine/Diphenyl Sulfone

1.
1. School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, P. R. China;
2. Department of Chemical and Pharmaceutical Engineering, Chengxian College, Southeast University, Nanjing 210088, P. R. China

Received Date: 7 April 2015
Available Online: 12 June 2015
Fund Project: 国家自然科学基金(51103023, 21173042) (51103023, 21173042) 国家重点基础研究发展规划项目(973) (2013CB932900) (973) (2013CB932900)江苏省高校自然科学研究项目(14KJB150003)资助 (14KJB150003)

A series of thermally activated delayed fluorescence (TADF) materials (1-3) based on triphenylamine/diphenyl sulfone were synthesized by Suzuki cross-coupling reactions. The optical, electrochemical, delayed fluorescence, and thermal properties of these materials were characterized by UVVis spectroscopy, time-resolved fluorescence spectroscopic measurements, cyclic voltammetry (CV), theoretical calculations, thermal gravimetric analyses, and differential scanning calorimetry. Materials 1-3 are bipolar compounds based on intramolecular charge transfer (ICT), and they have small energy gaps between the singlet and triplet (ΔE_ST) of 0.46, 0.39, and 0.29 eV, respectively. The results of fluorescent quantum yields and fluorescent lifetime indicate that these materials can emit delayed fluorescence, and material 3 has the greatest potential as a TADF emitter among materials 1-3. The highest occupied molecular orbital (HOMO) energy levels of materials 1-3 were estimated to be -4.91, -4.89, and -4.89 eV, respectively. From the HOMO energy levels and the optical bandgap (E_g) values, the lowest unoccupied molecular orbital (LUMO) energy levels were estimated to be -1.74, -1.89, and -1.94 eV for materials 1-3, respectively. Thermal gravimetric analysis results reveal that materials 1-3 have high thermal decomposition temperatures (T_d), corresponding to 5% weight loss at 436, 387, and 310 ℃, respectively.
- Triphenylamine,
- Diphenyl sulfone,
- Bipolar,
- Intramolecular charge transfer,
- Energy gap between singlet and triplet,
- Thermally activated delayed fluorescence
1. [1]
  
  (1) Baldo, M. A.; O'Brien, D. F.; You, Y.; Shoustikov, A.; Sibley, S.; Thompson, M. E.; Forrest, S. R. Nature 1998, 395, 151. doi: 10.1038/25954
2. [2]
  (2) Tao, Y. T.; Yang, C. L.; Qin, J. G. Chem. Soc. Rev. 2011, 40, 2943. doi: 10.1039/c0cs00160k
3. [3]
  (3) Hashimoto, M.; Igawa, S.; Yashima, M.; Kawata, I.; Hoshino, M.; Osawa, M. J. Am. Chem. Soc. 2011, 133, 10348. doi: 10.1021/ja202965y
4. [4]
  (4) Zhang, Q.; Komino, T.; Huang, S.; Matsunami, S.; ushi, K.; Adachi, C. Adv. Funct. Mater. 2012, 22, 2327. doi: 10.1002/adfm.v22.11
5. [5]
  (5) Zhang, D.; Duan, L.; Li, C.; Li, Y.; Li, H.; Zhang, D.; Qiu, Y. Adv. Mater. 2014, 26, 5050. doi: 10.1002/adma.201401476
6. [6]
  (6) Tao, Y.; Yuan, K.; Chen, T.; Xu, P.; Li, H.; Chen, R.; Zheng, C.; Zhang, L.; Huang, W. Adv. Mater. 2014, 26, 7931. doi: 10.1002/adma.v26.47
7. [7]
  (7) Uoyama, H.; ushi, K.; Shizu, K.; Nomura, H.; Adachi, C. Nature 2012, 492, 234. doi: 10.1038/nature11687
8. [8]
  (8) Nakanotani, H.; Higuchi, T.; Furukawa, T.; Masui, K.; Morimoto, K.; Numata, M.; Tanaka, H.; Sagara, Y.; Yasuda, T.; Adachi, C. Nat. Commun. 2014, 5, 4016.
9. [9]
  (9) Wang, H.; Xie, L.; Peng, Q.; Meng, L.; Wang, Y.; Yi, Y.; Wang, P. Adv. Mater. 2014, 26, 5198. doi: 10.1002/adma.201401393
10. [10]
  (10) Zhang, Q.; Li, B.; Huang, S.; Nomura, H.; Tanaka, H.; Adachi, C. Nat. Photon. 2014, 8, 326. doi: 10.1038/nphoton.2014.12
11. [11]
  (11) Sato, K.; Shizu, K.; Yoshimura, K.; Kawada, A.; Miyazaki, H.; Adachi, C. Phys. Rev. Lett. 2013, 110, 247401. doi: 10.1103/PhysRevLett.110.247401
12. [12]
  (12) Christensen, P. R.; Nagle, J. K.; Bhatti, A.; O'Wolf, M. J. Am. Chem. Soc. 2013, 135, 8109. doi: 10.1021/ja401383q
13. [13]
  (13) Zheng, C. J.; Wang, J.; Ye, J.; Lo, M. F.; Liu, X. K.; Fung, M. K.; Zhang, X. H.; Lee, C. S. Adv. Mater. 2013, 25, 2205. doi: 10.1002/adma.201204724
14. [14]
  (14) Ye, J.; Chen, Z.; Fung, M. K.; Zheng, C. J.; Ou, X. M.; Zhang, X. H.; Yuan, Y.; Lee, C. S. Chem. Mater. 2013, 25, 2630. doi: 10.1021/cm400945h
15. [15]
  (15) Huang, T. H.; Lin, J. T.; Chen, L. Y.; Lin, Y. T.; Wu, C. C. Adv. Mater. 2006, 18, 602.
16. [16]
  (16) Sasabe, H.; Seino, Y.; Kimura, M.; Kido, J. Chem. Mater. 2012, 24, 1404. doi: 10.1021/cm3006748
17. [17]
  (17) Wu, S.; Aonuma, M.; Zhang, Q.; Huang, S.; Nakagawa, T.; Kuwabara, K.; Adachi, C. J. Mater. Chem. C 2014, 2, 421. doi: 10.1039/C3TC31936A
18. [18]
  (18) Huang, B.; Qi, Q.; Jiang, W.; Tang, J.; Liu, Y.; Fan, W.; Yin, Z.; Shi, F.; Ban, X.; Xu, H.; Sun, Y. Dyes and Pigments 2014, 111, 135. doi: 10.1016/j.dyepig.2014.06.008
19. [19]
  (19) Zhang, Q.; Li, J.; Shizu, K.; Huang, S.; Hirata, S.; Miyazaki, H.; Adachi, C. J. Am. Chem. Soc. 2012, 134, 14706. doi: 10.1021/ja306538w
20. [20]
  (20) Im, Y.; Lee, J. Y. Chem. Mater. 2014, 26, 1413. doi: 10.1021/cm403358h
21. [21]
  (21) Wu, Y. X.; Ren, H. Y.; Wu, Y. F.; Wang, B. X. Acta Chim. Sin. 2015, 73 (1), 53. [巫友雄, 任泓扬, 吴义芳, 王炳喜. 化学学报, 2015, 73 (1), 53.]
22. [22]
  (22) Lee, S. Y.; Yasuda, T.; Yang, Y. S.; Zhang, Q.; Adachi, C. Angew. Chem. Int. Edit. 2014, 53, 6402. doi: 10.1002/anie.201402992
23. [23]
  (23) Ouyang, M.; Wu, Q. C.; Yu, Z. W.; Li, H. F.; Zhang, C. Acta Phys. -Chim. Sin. 2014, 30 (7), 1341. [欧阳密, 吴启超, 余振伟, 李洪飞, 张诚. 物理化学学报, 2014, 30 (7), 1341.] doi: 10.3866/PKU.WHXB201405041
24. [24]
  (24) Sumalekshmy, S.; pidas, K. R. J. Phys. Chem. B 2004, 108, 3705. doi: 10.1021/jp022549l
25. [25]
  (25) Mataga, N.; Kaifu, Y.; Koizumi, M. Bull. Chem. Soc. Jap. 1956, 29, 465. doi: 10.1246/bcsj.29.465
1. [1]
  Yuting DU , Jing YUAN , Peiyao DENG . Synthesis and application of a fluorescent probe for the detection of reduced glutathione. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1331-1337. doi: 10.11862/CJIC.20240461
2. [2]
  Yingpeng ZHANG , Xingxing LI , Yunshang YANG , Zhidong TENG . A pyrazole-based turn-off fluorescent probe for visual detection of hydrazine. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1301-1308. doi: 10.11862/CJIC.20250064
3. [3]
  Zihan Cheng , Kai Jiang , Jun Jiang , Henggang Wang , Hengwei Lin . Achieving thermal-stimulus-responsive dynamic afterglow from carbon dots by singlet-triplet energy gap engineering through covalent fixation. Acta Physico-Chimica Sinica, 2026, 42(2): 100169-0. doi: 10.1016/j.actphy.2025.100169
4. [4]
  Xiaogang YANG , Xinya ZHANG , Jing LI , Huilin WANG , Min LI , Xiaotian WEI , Xinci WU , Lufang MA . Synthesis, structure, and photoelectric properties of Zinc(Ⅱ)-triphenylamine based metal-organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2078-2086. doi: 10.11862/CJIC.20250167
5. [5]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-0. doi: 10.3866/PKU.WHXB202309027
6. [6]
  Weikang Wang , Yadong Wu , Jianjun Zhang , Kai Meng , Jinhe Li , Lele Wang , Qinqin Liu . Green H₂O₂ synthesis via melamine-foam supported S-scheme Cd_0.5Zn_0.5In₂S₄/S-doped carbon nitride heterojunction: synergistic interfacial charge transfer and local photothermal effect. Acta Physico-Chimica Sinica, 2025, 41(8): 100093-0. doi: 10.1016/j.actphy.2025.100093
7. [7]
  Meng Aoyun , Li Zhenhua , Xiong Guoyuan , Li Zhen , Zhang Jinfeng . S-scheme heterojunction Al₆Si₂O₁₃/BiOBr with enhanced charge transfer effect for efficient and stable photocatalytic degradation of triazophos and dichlorvos pesticides. Acta Physico-Chimica Sinica, 2026, 42(5): 100186-. doi: 10.1016/j.actphy.2025.100186
8. [8]
  Pengli GUAN , Renhu BAI , Xiuling SUN , Bin LIU . Trianiline-derived aggregation-induced emission luminogen probe for lipase detection and cell imaging. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1817-1826. doi: 10.11862/CJIC.20250058
9. [9]
  Qi Wu , Changhua Wang , Yingying Li , Xintong Zhang . Enhanced photocatalytic synthesis of H₂O₂ by triplet electron transfer at g-C₃N₄@BN van der Waals heterojunction interface. Acta Physico-Chimica Sinica, 2025, 41(9): 100107-0. doi: 10.1016/j.actphy.2025.100107
10. [10]
  Limin Zhao , Kaiqiang Xu , Chuanbiao Bie . 2D COF photocatalyst with highly stabilized tautomeric transition and singlet oxygen generation. Acta Physico-Chimica Sinica, 2026, 42(4): 100216-0. doi: 10.1016/j.actphy.2025.100216
11. [11]
  Weilai Yu , Chuanbiao Bie . Unveiling S-Scheme Charge Transfer Mechanism. Acta Physico-Chimica Sinica, 2024, 40(4): 2307022-0. doi: 10.3866/PKU.WHXB202307022
12. [12]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
13. [13]
  Hequn Yang , Fei Rao , Dean Pan , Liu Chen , Numan Abbas , Gangqiang Zhu . Rare earth praseodymium single atoms on g-C₃N₄ tubes for enhanced in-plane charge transfer towards H₂O₂ production in pure water. Acta Physico-Chimica Sinica, 2026, 42(6): 100210-0. doi: 10.1016/j.actphy.2025.100210
14. [14]
  Jichao XU , Ming HU , Xichang CHEN , Chunhui WANG , Leichen WANG , Lingyi ZHOU , Xing HE , Xiamin CHENG , Su JING . Construction and hydrogen peroxide-activated chemodynamic activity of ferrocene?benzoselenadiazole conjugate. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1495-1504. doi: 10.11862/CJIC.20250144
15. [15]
  Jin Yan , Chengxia Tong , Yajie Li , Yue Gu , Xuejian Qu , Shigang Wei , Wanchun Zhu , Yupeng Guo . Construction of a “Dual Support, Triple Integration” Chemical Safety Practical Education System. University Chemistry, 2024, 39(7): 69-75. doi: 10.12461/PKU.DXHX202405008
16. [16]
  Linghua Chen . 基于双联动“三学”模式的食品专业分析化学教学改革. University Chemistry, 2025, 40(8): 78-91. doi: 10.12461/PKU.DXHX202409095
17. [17]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
18. [18]
  Wanmin Cheng , Juan Du , Peiwen Liu , Yiyun Jiang , Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066
19. [19]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
20. [20]
  Mengfan Gong , Dongju Zhang . Estimating Delocalization Energies of 1,3-Butadiene and Benzene with Isodesmic Reactions: A Relatively Precise Approach. University Chemistry, 2026, 41(4): 457-463. doi: 10.12461/PKU.DXHX202505036

Get Citation

PDF

XML

Metrics

PDF Downloads(285)
Abstract views(1126)
HTML views(47)

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