高等学校化学学报

高等学校化学学报

• 研究论文 • 上一篇    下一篇

α-含氧取代酞菁的聚集性质研究

黄新1, 赵福群1, 李忠玉1,2, 赵澎1, 唐应武1, 张复实1   

    1. 清华大学化学系, 有机光电子与分子工程教育部重点实验室, 北京 100084;
    2. 吉林化工学院化学工程系, 吉林 132022
  • 收稿日期:2006-10-08 修回日期:1900-01-01 出版日期:2007-03-10 发布日期:2007-03-10
  • 通讯作者: 张复实

Studies on Aggregation Behavior of α-Oxygen-bearing Substituted Phthalocyanines

HUANG Xin1, ZHAO Fu-Qun1, LI Zhong-Yu1,2, ZHAO Peng1, TANG Ying-Wu1, ZHANG Fu-Shi1   

    1. Key Laboratory of Organic Photoelectronic and Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, China;
    2. Department of Chemical Engineering, Jilin Institute of Chemical Technology, Jilin 132022, China
  • Received:2006-10-08 Revised:1900-01-01 Online:2007-03-10 Published:2007-03-10
  • Contact: ZHANG Fu-Shi

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摘要： 以3-硝基邻苯二腈为原料分别与苯酚和甲醇反应合成3-苯氧基邻苯二腈和3-甲氧基邻苯二腈, 这些α-取代的邻苯二腈以二甲氨基乙醇为溶剂, 在有无醋酸锌条件下环合, 分别形成α-四苯氧基锌酞菁、α-四苯氧基无金属酞菁、α-四甲氧基锌酞菁、α-四甲氧基无金属酞菁, 对产物结构进行了表征. 光谱分析结果表明, 此类锌酞菁在氯仿等非配位溶剂中能自发形成J型聚集体, 其Q带出现一个红移吸收带, 经UV-Vis光谱、荧光光谱及MALDI-TOF质谱分析表明, 该聚集体的形成机理为基于酞菁分子间的锌-氧自配位相互作用.

关键词: α-含氧取代酞菁, J型聚集体, 锌-氧自配位

Abstract: 3-Phen/methoxyphthalonitrile was obtained via the reaction of 3-nitrophthalonitrile with phenol/methanol under the catalysis of anhydrous potassium carbonate. α-Aryl/alkoxy substituted phthalocyanines were synthesized by treating the corresponding substituted phthalonitriles in refluxing dimethylaminoethanol with or without metal acetate and were fully characterized by UV-Vis, 1H NMR, MS spectra and elemental analysis. It was found that α-oxygen-bearing substituted zinc phthalocyanines 1 and 3 can form J-type aggregates easily in non-coordinating solvents. The MALDI-TOF MS for the samples of 1 prepared from chloroform solutions gives the monomer and aggregate signals. The aggregates are broken up when a coordinating solvent is added to the solution. A possible mechanism on the formation of this self-assembly was proposed, which it was driven by the complementary coordination of the ether oxygen in the aryl/alk-oxy groups of one molecule to the core Zn of another molecule of phthalocyanine.

Key words: α-Oxygen-bearing substituted phthalocyanine, J-aggregate, Zn—O self-coordination

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