Phosphonic Acid Functionalized Asymmetric Phthalocyanines: Synthesis, Modification of Indium Tin Oxide, and Charge Transfer

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• 作者：Nathan W. Polaske ; Hsiao-Chu Lin ; Anna Tang ; Mayunk Mayukh ; Luis E. Oquendo ; John T. Green ; Erin L. Ratcliff ; Neal R. Armstrong ; S. Scott Saavedra ; Dominic V. McGrath
• 刊名：Langmuir
• 出版年：2011
• 出版时间：December 20, 2011
• 年：2011
• 卷：27
• 期：24
• 页码：14900-14909
• 全文大小：1059K
• 年卷期：v.27,no.24(December 20, 2011)
• ISSN：1520-5827

文摘

Metalated and free-base A₃B-type asymmetric phthalocyanines (Pcs) bearing, in the asymmetric quadrant, a flexible alkyl linker of varying chain lengths terminating in a phosphonic acid (PA) group have been synthesized. Two parallel series of asymmetric Pc derivatives bearing aryloxy and arylthio substituents are reported, and their synthesis and characterization through NMR, combustion analysis, and MALDI-MS are described. We also demonstrate the modification of indium tin oxide (ITO) substrates using the PA functionalized asymmetric Pc derivatives and monitoring their electrochemistry. The PA functionalized asymmetric Pcs were anchored to the ITO surface through chemisorption and their electrochemical properties characterized using cyclic voltammetry to investigate the effects of PA structure on the thermodynamics and kinetics of charge transfer. Ionization energies of the modified ITO surfaces were measured using ultraviolet photoemission spectroscopy.