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现代化工  2020, Vol. 40 Issue (5): 117-121,127    DOI: 10.16606/j.cnki.issn0253-4320.2020.05.027
  科研与开发 本期目录 | 过刊浏览 | 高级检索 |
蒽醌氧桥双核锌酞菁的合成与性能研究
徐康, 周雪飞, 王秀秀, 张学俊
中北大学理学院, 山西 太原 030051
Synthesis of binuclear zinc phthalocyanine by anthraquinone oxygen-bridged method and characterization
XU Kang, ZHOU Xue-fei, WANG Xiu-xiu, ZHANG Xue-jun
School of Science, North University of China, Taiyuan 030051, China
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摘要 以1,5-二羟基蒽醌、4-硝基邻苯二甲腈、3,5-二甲基苯酚、β-萘酚为主要原料,合成了3种不同的邻苯二甲腈衍生物前驱体,再经1,8-二氮杂双环[5.4.0]十一碳-7-烯催化聚合成9(10),16(17),23(24)-三[3,5-二甲基苯氧基]-2(3)-(1,5-二氧基蒽醌)双核锌酞菁(D-CPc)和9(10),16(17),23(24)-三[β-萘氧基]-2(3)-(1,5-二氧基蒽醌)双核锌酞菁(β-CPc)。利用FT-IR、UV-Vis、1H-NMR、元素分析、循环伏安法对2种化合物的特性进行了表征。结果表明,D-CPc和β-CPc的Q带分别发生11、10 nm的红移,在400~600 nm范围内表现出明显的紫外光谱吸收,弥补了无取代酞菁在400~600 nm范围内无吸收的缺陷,并且在0.1×10-5~1.0×10-5 mol/L的DMF溶液中表现出良好溶解性。循环伏安法研究表明,D-CPc和β-CPc的ELUMO值分别为-3.17、-3.26 eV,EHOMO值分别为-5.16、-5.10 eV,与TiO2能级和氧化还原电对能级相匹配,满足能带间隙规则,能够实现染料的氧化还原。
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徐康
周雪飞
王秀秀
张学俊
关键词:  双核酞菁  蒽醌  紫外光谱  能带间隙    
Abstract: Three kinds of phthalonitrile derivatives precursors are synthesized with 1,5-dihydroxyanthraquinone,4-nitrophthalonitrile,3,5-dimethylphenol and β-naphthol as main raw materials.The precursors are then catalyzed by DBU to form 9(10),16(17),23(24)-tris -2(3)-(1,5-dioxyanthraquinone) binuclear zinc phthalocyanine (D-CPc) and 9(10),16(17),23(24)-tris-2(3)-(1,5-dioxyanthraquinone) binuclear zinc phthalocyanine (β-CPc).Two compounds prepared are fully characterized by FT-IR,UV-Vis,1HNMR,elemental analysis,and cyclic voltammetry.It is shown that Q bands of both D-CPc and β-CPc undergo 11 nm and 10 nm of red shift,respectively.Both compounds exhibit obvious absorption in the range of 400-600 nm,while non-substituted phthalocyanine shows no-absorption in the range of 400-600 nm.They also show an excellent solubility in 0.1×10-5-1.0×10-5 mol·L-1 DMF solution.Cyclic voltammetry studies show that ELUMO values of D-CPc and β-CPc are -3.17 and -3.26 eV,respectively,and their EHOMO values are -5.16 and -5.10 eV,respectively.They can match with TiO2 energy level and redox electric pair energy level,meet band gap rules,and realize redox of dyes.
Key words:  binuclear phthalocyanine    anthraquinone    UV spectrum    band gap
收稿日期:  2019-07-09      修回日期:  2020-03-07          
ZTFLH:  TQ612.3  
基金资助: 山西省回国留学人员科研资助项目(2015-078);山西省自然科学基金资助项目(2015011011)
通讯作者:  张学俊(1971-),男,博士,教授,主要从事功能有机分子的合成与研究,通讯联系人,zhangxuejun@nuc.edu.cn。    E-mail:  zhangxuejun@nuc.edu.cn
作者简介:  徐康(1994-),男,硕士研究生,研究方向为酞菁类光电材料的合成,915925198@qq.com
引用本文:    
徐康, 周雪飞, 王秀秀, 张学俊. 蒽醌氧桥双核锌酞菁的合成与性能研究[J]. 现代化工, 2020, 40(5): 117-121,127.
XU Kang, ZHOU Xue-fei, WANG Xiu-xiu, ZHANG Xue-jun. Synthesis of binuclear zinc phthalocyanine by anthraquinone oxygen-bridged method and characterization. Modern Chemical Industry, 2020, 40(5): 117-121,127.
链接本文:  
https://www.xdhg.com.cn/CN/10.16606/j.cnki.issn0253-4320.2020.05.027  或          https://www.xdhg.com.cn/CN/Y2020/V40/I5/117
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