Synthesis and Photoelectricity of Novel Zn Metal Complex Based on 8-Hydroxyquinoline with Thiophene Group†

doi:10.7503/cjcu20130487

Abstract

Abstract:

8-Hydroxyquinoline has long been employed as analytical and separating agents due to its universal chelating ability offered by the heterocyclic N and phenolate O atoms and fiuorescent property possessed by the conjugate system. In order to increase its fluorescence capability and conjugate system, 3-thiophene has been added. A novel 8-hydroxyquinoline derivative ligand containing thiophene group (E)-2-[2-(3-thiophenyl)ethenyl]-8-hydroxyquinoline(4) and its corresponding zinc complex(5) were synthesized and identified via ¹H NMR, FTIR, UV-Vis, X-ray structural analysis and elemental analyses. The crystal structures of intermediate (E)-2-[2-(3-thiophenyl)ethenyl]-8-acetoxyquinoline(3) and ligand 4 were characterized by single-crystal X-ray diffraction. X-Ray structural analysis showed that there was no obvious hydrogen-bonding interaction between the molecules of compound 3. The crystal reticular structure of compound 4 was constructed as a result of intermolecular O-H…S hydrogen bonds. The aggregation behaviors of zinc salts and compound 4 in solutions were investigated with a variety of techniques, including ¹H NMR, UV-Vis and fluorescence.The fluorescence lifetime of complex 5 was determined in the solid state and its τ value is 18.8 ms. Organic light-emitting diodes built using complex 5 emitted yellow light, in which the 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene(TPBi) acts as the electronic transmission layer, while N,N'-bis-(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine(NPB) acts as hole transport material.

Key words: Thiophene, 8-Hydroxyquinoline, Zinc complex, NMR titration, Fluorescence lifetime, Electroluminescent device

CLC Number:

O622.7

TrendMD:

TANG Yinmin, HUO Yanping, HU Sheng, ZHANG Kun, ZHAO Fenghua, OUYANG Xinhua. Synthesis and Photoelectricity of Novel Zn Metal Complex Based on 8-Hydroxyquinoline with Thiophene Group^†[J]. Chem. J. Chinese Universities, 2014, 35(1): 48.

Figures/Tables 10

Scheme 1 Synthetic route of target compound

Table 1 Crystallographic data for compounds 3 and 4

Compound	3	4	Z	8	4
Empirical formula	C₁₇H₁₃NO₂S	C₁₅H₁₁NOS	rρ_c/(g·cm^-3)	1.338	1.371
M_r	295.34	253.31	μ/mm	0.224	0.249
T/K	173(2)	173(2)	F(000)	1232	528
Crystal system	Orthorhombic	Orthorhombic	S	1.028	1.139
Space group	Pbca	P2₁2₁2₁	Reflections collected	14825	5768
a/nm	115.860(18)	61.344(15)	Unique collected	2865	2378
b/nm	97.043(15)	81.39(2)	R_int	0.0216	0.0231
c/nm	260.81(4)	245.85(6)	$R 1 a$ [I>2(I)]	0.0358	0.0515
V/nm³	2932400(8)	1227500(5)	w $R 2 b$ (all data)	0.1357	0.1593

Table 1 Crystallographic data for compounds 3 and 4

Compound	3	4	Z	8	4
Empirical formula	C₁₇H₁₃NO₂S	C₁₅H₁₁NOS	rρ_c/(g·cm^-3)	1.338	1.371
M_r	295.34	253.31	μ/mm	0.224	0.249
T/K	173(2)	173(2)	F(000)	1232	528
Crystal system	Orthorhombic	Orthorhombic	S	1.028	1.139
Space group	Pbca	P2₁2₁2₁	Reflections collected	14825	5768
a/nm	115.860(18)	61.344(15)	Unique collected	2865	2378
b/nm	97.043(15)	81.39(2)	R_int	0.0216	0.0231
c/nm	260.81(4)	245.85(6)	$R 1 a$ [I>2(I)]	0.0358	0.0515
V/nm³	2932400(8)	1227500(5)	w $R 2 b$ (all data)	0.1357	0.1593

Fig.1 Molecular structures of compounds 3(A) and 4(B)

Fig.2 View of the packing mode of compound 3 along the b axis

Fig.3 Intermolecular hydrogen-bonding interaction of compound 4

Table 2 Hydrogen bond lengths and bond angles of compound 4

D-H…A	D-H/nm	H…A/nm	D…A/nm	∠D-H…A/(°)
O1-H1…N1	0.085	0.218	0.26521	115
C11-H11A…N1	0.095	0.250	0.28423	101

Fig.4 Crystal packing diagrams of compounds 3(A) and 4(B)

Fig.5 Fluorescence decay profiles of complex 5■ Fluorescence decay of complex 5; -- curve fitting of complex 5.

Fig.6 Electroluminescent spectra of complex 5■ Device A; ● device B; ▲ device C.

Table 3 Electroluminescent parameters of complex 5 in different device structures

Device	Luminance/(cd·m^-2)	Voltage of turn-on/V	Efficiency/(cd·A^-1)
A	980	5.2	0.84
B	420	8.6	0.22
C	540	8.2	0.36

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