Synthesis and optical properties of trifluoroethoxy-substituted double-decker phthalocyanines
Synthesis and optical properties of trifluoroethoxy-substituted double-decker phthalocyanines
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DOI：
10.1142/s1088424614500862
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发表时间：
2014-10-01
影响因子：
1.5
通讯作者：
Shibata, Norio
中科院分区：
文献类型：
--
作者：
Mori, Satoru;Ogawa, Naoya;Shibata, Norio
首次研究了三氟乙氧基取代双层酞菁的合成。三氟乙氧基取代的邻苯二腈在1,8-重氮双环[5.4.0]十一-7-烯存在下，在正辛醇中与乙酰丙酮水合物镧系化合物反应。镧和铕被选为中心金属。邻苯二腈，包括在-或-位置的一个三氟乙氧基取代基，被很好地诱导成双层酞菁。在α位置有两个三氟乙氧基取代基的邻苯二腈没有反应，尽管我们成功地将-二取代的邻苯二腈引入双层酞菁。全三氟乙氧基涂覆的邻苯二腈根本不发生反应。外围三氟乙氧基引起的憎氟排斥和位阻可能是双层结构难以形成的原因。研究了所得的三氟乙氧基取代双层酞菁的吸收光谱和荧光光谱。
The synthesis of trifluoroethoxy-substituted double-decker phthalocyanines was investigated for the first time. Trifluoroethoxy-substituted phthalonitriles reacted with lanthanide acetylacetonate hydrate in n-octanol in the presence of 1,8-diazabicyclo[5.4.0] undec-7-ene when refluxed. La and Eu were chosen as central metals. Phthalonitriles, including one trifluoroethoxy substituent at the alpha- or beta-position, were nicely induced to double-decker phthalocyanines. Phthalonitrile having two trifluoroethoxy substituents at alpha-positions did not react, although we succeeded in leading beta-di-substituted phthalonitrile to double-decker phthalocyanines. Fully trifluoroethoxy-coated phthalonitrile did not react at all. Fluorophobic repulsion and steric hindrance caused by outlying trifluoroethoxy groups could be responsible for the difficulty in the formation of a double-decker structure. Absorption and fluorescence spectra of trifluoroethoxy-substituted double-decker phthalocyanines obtained were also investigated.