Citation: Qiao-Wen CHANG, Zhu-An CHEN, Lu FENG, Wen JIANG, Cai-Xian YAN, Wei-Ping LIU, Fu-Quan BAI. Synthesis and photophysical properties of phenylquinoline iridium complexes controlled by electron-withdrawing groups[J]. Chinese Journal of Inorganic Chemistry, ;2023, 39(2): 255-262. doi: 10.11862/CJIC.2022.283 shu

Synthesis and photophysical properties of phenylquinoline iridium complexes controlled by electron-withdrawing groups

1.
State Key Laboratory of Advanced Technologies for Comprehensive Utilization of Platinum Metals, Kunming Institute of Precious Metals, Kunming Guiyan New Material Technology Co., Ltd., Yunnan Precious Metals Lab Co., Ltd., Kunming 650106, China
2.
Institute of Theoretical Chemistry, College of Chemistry, Jilin University, Changchun 130023, China

Corresponding author: Cai-Xian YAN, ycx19860706@163.com Fu-Quan BAI, Baifq@jlu.edu.cn
Received Date: 14 July 2022
Revised Date: 15 November 2022

Figures(5)

To study the effect of substituents on iridium phosphorescent complexes, fluorine, methoxy, or trifluoromethyl were introduced into positions 2 and 4 of phenyl at the same time to obtain 2, 4-disubstituted phenyl-4-methylquinoline (2, 4-2R-mpq). Three new iridium phosphorescent complexes (2, 4-2R-mpq)₂Ir(tmd) (R=F (1), MeO (2), CF₃ (3)) were synthesized by using 2, 2, 6, 6-tetramethylheptanedione (tmd) as the auxiliary ligand, and 2, 4-2R-mpq with the electron-withdrawing group as the main ligands. The compositions and chemical structures of the complexes were characterized by elemental analysis, NMR spectroscopy, and single-crystal X-ray diffraction. The three iridium complexes belong to the triclinic system with the P1 space group. The photophysical properties of the complexes were studied by UV - Vis absorption spectroscopy, photoluminescence spectroscopy, and theory calculation. The results indicate that complexes 1, 2, and 3 with the photoluminescence quantum yields of 96%, 80%, and 80% exhibited maximum emission peaks at 570, 582, and 604 nm, respectively. When F and MeO are introduced into the 2 and 4 positions of phenyl on the main ligand, the electron cloud of complexes 1 and 2 are aggregated, while the CF₃ is introduced, and the electron cloud of the complex is dispersed. Compared with complex 3, the emission wavelengths of complexes 1 and 2 had a significant blue shift. Different from traditional cognition, the methoxyl group represents an electron-withdrawing group.
- iridium(Ⅲ) complexes,
- phosphorescent materials,
- phenylquinoline,
- electron-withdrawing group,
- photophysical properties
1. [1]
  Tsujimura T. OLED Displays: Fundamentals and Applications. Hoboken: John Wiley & Sons, Inc., 2012: 5-30
2. [2]
  Tang C W, Vanslyke S A. Organic electroluminescent diodes[J]. Appl. Phys. Lett., 1987,51(12):913-915. doi: 10.1063/1.98799
3. [3]
  Reineke S, Linder F, Schwartz G, Seidler Nico, Walzer K, Lüssem B, Leo K. White organic light-emitting diodes with fluorescent tube efficiency[J]. Nature, 2009,459(7244):234-238. doi: 10.1038/nature08003
4. [4]
  YAO Y, XIAO J, TAN J F, WANG J, ZHU M, YIN Z Y, CAO L F. Improved performance with a hybrid cathodic interfacial layer in OLEDs[J]. Spectroscopy and Spectral Analysis, 2019,39(11):3383-3387.
5. [5]
  LIU Z W, BIAN Z Q, HUANG C H. The electroluminescence of metal complexes. Beijing: Science Press, 2019: 78-96
6. [6]
  WANG Y, WEI C D, GE G P, WANG S, LIANG Y X. Synthesis, crystal structures and photophysical properties of ionic iridium(Ⅲ) pyrimidine complexes[J]. Chinese J. Inorg. Chem., 2018,34(2):346-352.
7. [7]
  LIAO H S, GAN J Y, XIA X, HU Y X, XIE D D, ZHANG D Y, LI X. Synthesis of fluorinated diphenylbenzimidazole iridium complexes based on different auxiliary ligands and solution-processed electroluminescent devices[J]. Chinese J. Inorg. Chem., 2022,38(3):399-406.
8. [8]
  CHEN M, WANG X M, HE Y H, YANG J, WANG S, TONG B H. Synthesis and electroluminescence properties of iridium complex based on trifluoroacetylphenyl quinolone ligand[J]. Chinese J. Inorg. Chem., 2015,31(12):2285-2290.
9. [9]
  ZHOU Y H, XU Q L, LIU C L, XU J J. Synthesis and opto-electronic property of three green iridium(Ⅲ) complexes[J]. Chinese J. Inorg. Chem., 2020,36(7):1267-1274.
10. [10]
  Ruben D C, Enrique O, Henk J B. Luminescent Ionic Transition-Metal Complexes for Light-Emitting Electrochemical Cells[J]. Angew. Chem. Int. Ed., 2012,51(33):8178-8211.
11. [11]
  Fang K H, Wu L L, Huang Y T, Yang C H, Sun I W. Color tuning of iridium complexes-Part Ⅰ: Substituted phenylisoquinoline-based iridium complexes as the triplet emitter[J]. Inorg. Chim. Acta, 2006,359(2):441-450.
12. [12]
  TAO P. Design, synthesis, and excited states tuning of highly efficient iridium (Ⅲ) complexes for applications in optoelectronics. Taiyuan: Taiyuan University of Technology, 2017: 41-79
13. [13]
  Tao P, Li W L, Zhang J, Guo S, Zhao Q, Wang H, Wei B, Liu S J, Zhou X H, Yu Q, Xu B S, Huang W. Facile synthesis of highly efficient lepidine-based phosphorescent iridium(Ⅲ) complexes for yellow and white organic light-emitting diodes[J]. Adv. Funct. Mater., 2016,26(6):881-894.
14. [14]
  Kim D H, Cho N S, Oh H Y, Yang J H, Jeon W S, Park J S, Min C S, Kwon J H. Highly efficient red phosphorescent dopants in organic light-emitting devices[J]. Adv. Mater., 2011,23(24):2721-2726.
15. [15]
  Universal Display Corporation, Kwong R, Ma B, Xia C J, Alleyne B, Brooks J. Phosphorescent materials: WO2008/109824A2. 2008-09-12.
16. [16]
  Zhuang J Y, Li W F, Su W M, Liu Y, Shen Q, Liao L S, Zhou M. Highly efficient phosphorescent organic light-emitting diodes using a homoleptic iridium (Ⅲ) complex as a sky-blue dopant[J]. Org. Electron., 2013,14(10):2596-2601.
17. [17]
  Hammett L P. The effect of structure upon the reactions of organic compounds[J]. Benzene derivatives. J. Am. Chem. Soc., 1937,59(1):96-103.
18. [18]
  TIAN H R. Synthesis and electroluminescence properties of red phosphorescent iridium complex based on phenyquinazoline ligands. Dalian: Dalian University of Technology, 2021: 43-47
19. [19]
  Yan Z M, Wang Y P, Ding J Q, Wang Y, Wang L X. Methoxyl modification in furo[3, 2-c]pyridine based iridium complexes towards highly efficient green-and orange-emitting electrophosphorescent devices[J]. J. Mater. Chem. C, 2017,5(46):12221-12227.
20. [20]
  Tian H R, Liu D, Li J Y, Ma M Y, Lan Y, Wei W K, Niu R, Song K. Pure red phosphorescent iridium (Ⅲ) complexes containing phenylquinazoline ligands for highly efficient organic light-emitting diodes[J]. New J. Chem., 2021,45(25):11253-11260.
21. [21]
  CHANG Q W, CHEN Z A, WANG Z A, JIANG J, YU J, LIU W P, YAN C X, CHEN L. Iridium phosphorescent complexes based on the modified phenylquinoline ligand and their high-efficiency pure red organic electroluminescent device[J]. Chinese Journal of Luminescence, 2022,43(10):1583-1591.
1. [1]
  Qiaowen CHANG , Ke ZHANG , Guangying HUANG , Nuonan LI , Weiping LIU , Fuquan BAI , Caixian YAN , Yangyang FENG , Chuan ZUO . Syntheses, structures, and photo-physical properties of iridium phosphorescent complexes with phenylpyridine derivatives bearing different substituting groups. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 235-244. doi: 10.11862/CJIC.20240311
2. [2]
  Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
3. [3]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
4. [4]
  Wenjing ZHANG , Xiaoqing WANG , Zhipeng LIU . Recent developments of inorganic metal complex-based photothermal materials and their applications in photothermal therapy. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2356-2372. doi: 10.11862/CJIC.20240254
5. [5]
  Keweiyang Zhang , Zihan Fan , Liyuan Xiao , Haitao Long , Jing Jing . Unveiling Crystal Field Theory: Preparation, Characterization, and Performance Assessment of Nickel Macrocyclic Complexes. University Chemistry, 2024, 39(5): 163-171. doi: 10.3866/PKU.DXHX202310084
6. [6]
  Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
7. [7]
  Xueyu Lin , Ruiqi Wang , Wujie Dong , Fuqiang Huang . 高性能双金属氧化物负极的理性设计及储锂特性. Acta Physico-Chimica Sinica, 2025, 41(3): 2311005-. doi: 10.3866/PKU.WHXB202311005
8. [8]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
9. [9]
  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
10. [10]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
11. [11]
  Cheng Zheng , Shiying Zheng , Yanping Zhang , Shoutian Zheng , Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131
12. [12]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
13. [13]
  Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
14. [14]
  Yaping ZHANG , Tongchen WU , Yun ZHENG , Bizhou LIN . Z-scheme heterojunction β-Bi₂O₃ pillared CoAl layered double hydroxide nanohybrid: Fabrication and photocatalytic degradation property. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 531-539. doi: 10.11862/CJIC.20240256
15. [15]
  Meng Lin , Hanrui Chen , Congcong Xu . Preparation and Study of Photo-Enhanced Electrocatalytic Oxygen Evolution Performance of ZIF-67/Copper(I) Oxide Composite: A Recommended Comprehensive Physical Chemistry Experiment. University Chemistry, 2024, 39(4): 163-168. doi: 10.3866/PKU.DXHX202308117
16. [16]
  Zhao Lu , Hu Lv , Qinzhuang Liu , Zhongliao Wang . Modulating NH₂ Lewis Basicity in CTF-NH₂ through Donor-Acceptor Groups for Optimizing Photocatalytic Water Splitting. Acta Physico-Chimica Sinica, 2024, 40(12): 2405005-. doi: 10.3866/PKU.WHXB202405005
17. [17]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
18. [18]
  Wei Li , Ze Chang , Meihui Yu , Ying Zhang . Curriculum Ideological and Political Design of Piezoelectricity Measurement Experiments of Coordination Compounds. University Chemistry, 2024, 39(2): 77-82. doi: 10.3866/PKU.DXHX202308004
19. [19]
  Ji Qi , Jianan Zhu , Yanxu Zhang , Jiahao Yang , Chunting Zhang . Visible Color Change of Copper (II) Complexes in Reversible SCSC Transformation: The Effect of Structure on Color. University Chemistry, 2024, 39(3): 43-57. doi: 10.3866/PKU.DXHX202307050
20. [20]
  Cunling Ye , Xitong Zhao , Hongfang Wang , Zhike Wang . A Formula for the Calculation of Complex Concentrations Arising from Side Reactions and Its Applications. University Chemistry, 2024, 39(4): 382-386. doi: 10.3866/PKU.DXHX202310043

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(1299)
HTML views(300)

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