Synthesis and Fluorescent Properties of Polyesters Containing 8-Hydroxyquinoline Side Groups and Their Zn(Ⅱ) and Al(Ⅲ) Complexes

doi:10.11944/j.issn.1000-0518.2019.03.180229

Chinese Journal of Applied Chemistry ›› 2019, Vol. 36 ›› Issue (3): 306-313.DOI: 10.11944/j.issn.1000-0518.2019.03.180229

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Synthesis and Fluorescent Properties of Polyesters Containing 8-Hydroxyquinoline Side Groups and Their Zn(Ⅱ) and Al(Ⅲ) Complexes

ZHANG Bin,Sun Xuejiao,Lü Chengwei,YU Shijun()

School of Chemistry and Chemical Engineering,Liaoning Normal University,Dalian,Liaoning 116029,China

Received:2018-06-27 Accepted:2018-08-29 Published:2019-03-01 Online:2019-02-28
Contact: YU Shijun
Supported by:
Supported by the National Natural Science Foundation of China(No.21403100), the Science Research Project of the Department of Education of Liaoning Province(No.L2012383)

Abstract

Abstract:

Three kinds of novel polyesters containing 8-hydroxyquinoline side groups(P7~P9) were synthesized, and subsequently their zinc complexes(P7-Zn~P9-Zn) and aluminum complexes(P7-Al~P9-Al) were obtained by reactions with zinc acetate and aluminum chloride, respectively. The structures and properties of polyesters and their metal complexes were characterized by elemental analysis, infrared(IR), ultraviolet-visable spectroscopy(UV-Vis), proton nuclear magnetic resonance(¹H NMR), gel permeation chromatography(GPC), thermogravimetric analysis(TG), differential scanning calorimetry(DSC) and fluorescence spectroscopy. The polyesters obtained are soluble in N,N-dimethyl formamide(DMF), N,N-dimethyl acetamide(DMAC), dimethylsulfoxide(DMSO), and N-methyl pyrrolidone(NMP). Complexes P7-Zn~P9-Zn and P7-Al~P9-Al can be partially dissolved in DMF, DMAC, DMSO and NMP. The M_w and polydispersity index(PDI) of P7~P9 are 1.79×10⁴, 2.14×10⁴ and 2.52×10⁴ g/mol and 1.54, 1.64 and 1.72 , respectively. The 5% mass loss temperatures of P7~P9, P7-Zn~P9-Zn and P7-Al~ P9-Al are 291.6, 291.3, 284.9, 348.7, 339.2, 334.6, 316.1, 316.7 and 316.0 ℃, respectively. The glass transition temperatures(T_g) of P7~P9 are 121.8, 106.2 and 91.3 ℃, respectively, and T_g of their metal complexes are all higher than 180 ℃. Fluorescence emission peaks of P7~P9 in DMF solution appear at 413~418 nm, emitting weak purple light. Fluorescence emission peaks of P7-Zn~P9-Zn and P7-Al~P9-Al in DMF solution emerged at 509~513 and 485~487 nm, respectively, emitting strong green light, Fluorescence emission peaks of P7-Zn~P9-Zn and P7-Al~P9-Al in solid state located at 516~519 and 492~497 nm, respectively, emitting strong green light. The fluorescence quantum yields of P7~P9, P7-Zn~P9-Zn and P7-Al~P9-Al are 5.5%~8.4%, 21%~28% and 23%~29%, respectively.

Key words: 8-hydroxyquinoline, polyester, zinc complex, aluminum complex

ZHANG Bin,Sun Xuejiao,Lü Chengwei,YU Shijun. Synthesis and Fluorescent Properties of Polyesters Containing 8-Hydroxyquinoline Side Groups and Their Zn(Ⅱ) and Al(Ⅲ) Complexes[J]. Chinese Journal of Applied Chemistry, 2019, 36(3): 306-313.

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Synthesis and Fluorescent Properties of Polyesters Containing 8-Hydroxyquinoline Side Groups and Their Zn(Ⅱ) and Al(Ⅲ) Complexes

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