Subphthalocyanine-Fused Dimers and Trimers: Synthetic, Electrochemical, and Theoretical Studies

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• 作者：Rodrigo S. Iglesias ; Christian G. Claessens ; Tomas Torres ; M. Á ; ngeles Herranz ; Victor R. Ferro ; Jose M. Garc&iacute ; a de la Vega
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：April 13, 2007
• 年：2007
• 卷：72
• 期：8
• 页码：2967 - 2977
• 全文大小：637K
• 年卷期：v.72,no.8(April 13, 2007)
• ISSN：1520-6904

文摘

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Subphthalocyanine (SubPc)-fused dimers and trimers bearing fluorine, iodine, and thioether peripheralsubstituents were synthesized and characterized. Absorption spectroscopy and electrochemical studiesrevealed (i) that the substituents have a strong effect on the electronic properties of the macrocycles and(ii) that there is good communication between the subphthalocyaninic moieties within the oligomericstructures. Theoretical calculations at DFT/6-31G(d,p) computational level and electron density studiessupport the experimental findings. The frontier orbitals in the dimers and trimers were also shown to besignificantly altered with respect to those of SubPcs as a consequence of the extension of the conjugationassociated with symmetry breaking. Time-dependent density functional theory calculations reproducedthe differences observed in the UV-vis spectra of the fused dimers and the monomeric SubPcs.