Synthesis and Characterization of an Emissive Ag(I) Complex with a D-A Type Ligand Containing Two Electron-withdrawing Groups

doi:10.6023/A24020058

Acta Chimica Sinica ›› 2024, Vol. 82 ›› Issue (5): 486-492.DOI: 10.6023/A24020058 Previous Articles Next Articles

Article

具有双吸电子基团D-A型配体的Ag(I)发光配合物的合成与性能研究

赵雨晴^a^,^b, 梁栋^b, 贾吉慧^d, 余荣民^a^,^b^,^*(), 卢灿忠^b^,^c^,^*()

a 福州大学化学学院福州 350116
b 中国科学院福建物质结构研究所福州 350108
c 中国科学院大学福建学院福州 350108
d 福建理工大学材料科学与工程学院福州 350118

投稿日期:2024-02-21 发布日期:2024-04-11
基金资助:
国家自然科学基金(52073286); 国家自然科学基金(2021ZZ115); 国家自然科学基金(2021ZR132); 福建省自然科学基金(2021J011073); 福建省区域发展项目(2021H4008); 以及中国科学院科技服务网络计划(STS2023T3039)

Synthesis and Characterization of an Emissive Ag(I) Complex with a D-A Type Ligand Containing Two Electron-withdrawing Groups

Yuqing Zhao^a^,^b, Dong Liang^b, Jihui Jia^d, Rongmin Yu^a^,^b(), Can-Zhong Lu^b^,^c()

a College of Chemistry, Fuzhou University, Fuzhou 350116
b Fujian Institute of Research on the Structure of Matter, Fuzhou 350108
c Fujian College, University of Chinese Academy of Sciences, Fuzhou 350108
d School of Materials Science and Engineering, Fujian University of Science and Technology, Fuzhou 350118

Received:2024-02-21 Published:2024-04-11
Contact: *E-mail: rongmingyu@fjirsm.ac.cn; czlu@fjirsm.ac.cn
Supported by:
National Natural Science Foundation of China(52073286); National Natural Science Foundation of China(2021ZZ115); National Natural Science Foundation of China(2021ZR132); Natural Science Foundation of Fujian Province(2021J011073); regional development projects in Fujian Province(2021H4008); Science and Technology Service Network Initiative from the Chinese Academy of Sciences(STS2023T3039)

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Abstract

Thermally activated delayed fluorescence (TADF) materials have attracted significant attention in the field of organic light-emitting diodes (OLEDs) due to their tremendous application potential. The outermost electronic configuration of the Ag(I) complex is d¹⁰ configuration, with d orbitals always being filled. There is no metal-centred (MC) state, therefore the quenching effect caused by the MC state does not occur. This renders it an appropriate choice for the design and development of TADF materials. In this study, we designed and synthesized a novel D-A ligand, 9-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-4- (3-(pyridin-2-yl)-1H-pyrazole-1-yl)-[1,1'-biphenyl]-2-yl)-3,6-dimethoxy-9H-carbazole (L). The ligand employs 3,6-dimeth- oxy-9H-carbazole as the electron donor and comprises a bis-electron-donating group comprising triazine and pyridyl pyrazole as the electron acceptor. An ionic Ag(I) complex, Ag(L)(POP)(BF₄) (1), was synthesised utilising L as a nitrogen-containing bidentate ligand and bis[2-(diphenylphosphino)phenyl] ether (POP) as a phosphorus-containing bidentate ligand. The ligand L and complex 1 were characterised by ¹H and ¹³C nuclear magnetic resonance spectrometry, elemental analysis and X-ray single crystal diffraction analysis. The complex 1 belongs to the triclinic crystal system with space group P-1, with a=1.30213(4) nm, b=1.63383(4) nm, and c=1.93108(5) nm, α=92.941(2)°, β=105.247(3)°, γ=98.591(2)°, V=3.90076(18) nm³. The Ag⁺ion in complex 1 is tetrahedrally coordinated with a twisted tetrahedral coordination geometry. At room temperature, complex 1 in solid form emits strong green light under UV light, with a maximum at 490 nm. The fluorescence lifetime is 23.0 ns, the thermally activated delayed fluorescence (TADF) lifetime is 503.9 μs, and the photoluminescence quantum yield (PLQY) is 43.8%. The steady-state emission spectra and time-dependent photoluminescent spectra of complex 1 at different temperatures demonstrate that complex 1 exhibits TADF characteristics at room temperature.

Key words: Ag(I) complex, crystal structure, photoluminescence, density functional theory calculation, thermally activated delayed fluorescence

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Yuqing Zhao, Dong Liang, Jihui Jia, Rongmin Yu, Can-Zhong Lu. Synthesis and Characterization of an Emissive Ag(I) Complex with a D-A Type Ligand Containing Two Electron-withdrawing Groups[J]. Acta Chimica Sinica, 2024, 82(5): 486-492.

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Fig. & Tab. 6

Figure 1. ORTEP diagram of ligand L (left) and complex 1 (right)

Compound
Distance/nm	Ag1—N1	0.2452(4)
	Ag1—N2	0.2295(4)
	Ag1—P1	0.24142(13)
	Ag1—P2	0.24334(12)
Angle/(°)	P1—Ag1—P2	116.69(4)
	P1—Ag1—N1	103.55(11)
	N1—Ag1—N2	69.85(15)
	N2—Ag1—P2	111.25(11)
Dihedral angle/(°)	P1—Ag1—P1/ N1—Ag1—N2	78.090(116)

Table 1. Bond lengths (nm) and bond angles (°) of complex 1

Figure 2. (a) Absorption spectra of complex 1 in CH2Cl2 (2×10?5 mol/L) solution and the PL spectra at 298 and 77 K in solid state (λEx=365 nm); (b) transient PL decay spectra at 298 K for complex 1 (λEx=365 nm, λEm=490 nm)

298 K
Compound	λ_max/ nm	Ф_PL/ %	Ф_F^a/ %	Ф_TADF^a/ %	τ_F/ ns	τ_TADF/ μs
L	490	17.3	17.0	0.3	106.0	3272.4
1	490	43.8	5.2	38.6	23.0	503.9

Table 2. Photophysical data for ligand (L) and complex 1 in solid state at 298 K

Figure 3. (a) Time-resolved PL spectra of complex 1 in different time ranges at 298 K (λEx=365 nm, λEm=490 nm); (b) time-resolved PL spectra of complex 1 in different time ranges at 77 K (λEx=365 nm, λEm=530 nm)

Figure 4. HOMO－1, HOMO, LUMO and LUMO＋1 electron cloud distribution of ligand L (left) and complex 1 (right)

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具有双吸电子基团D-A型配体的Ag(I)发光配合物的合成与性能研究

Synthesis and Characterization of an Emissive Ag(I) Complex with a D-A Type Ligand Containing Two Electron-withdrawing Groups

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