Cationic cyclopentadienyliron azo-complexes: Synthesis, spectroscopic characterization, and molecular structure

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• 作者：Guanglei Li^a ; Yu Chen^a ; Junru Han^a ; Hui Ye^a ; Xiaoning Wang^b ; Tao Wang^a ; ^{wangtwj2000@163.com}
• 关键词：Cationic cyclopentadienyliron azo-complex (Azo-Fc) ; Synthesis ; Spectroscopy ; Photostability ; Geometric structure ; Frontier molecular orbital
• 刊名：Dyes and Pigments
• 出版年：2012
• 期刊代码：31_01437208
• 类别：ms
• 出版时间：August, 2012
• 卷：94
• 期：2
• 页码：314-319
• 文件大小：534 K

摘要

Two novel cationic cyclopentadienyliron azo-complexes (Azo-Fc) were synthesized by the S_NAr reaction of (畏⁶-chlorobenzene) (畏⁵-cyclopentadienyl) iron hexafluorophosphate (Fc-Cl) with 1-phenylazo-2-naphthol and 4-(4-nitrophenylazo)carbazole. They were characterized by IR, ¹H NMR, ¹³C NMR, and MS. The UV-vis spectral characteristics of the azo-complexes were investigated in four organic solvents of different degrees of polarity. These synthesized azo-complexes exhibited a bathochromic shift of the visible absorption maxima with the increase in conjugating skeleton. The study of photochemical properties reveals that the azo-complexes showed good photostability and that photolysis was difficult to realize. The geometric structures of the azo-complexes were optimized on the basis of density function theory at the B3PW91/Lanl2dz level. The energy levels of their frontier molecular orbitals were obtained.