Phosphonic acid functionalized asymmetric phthalocyanines: Synthesis, modification of indium tin oxide, and charge transfer

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

Research output: Contribution to journalArticle

27 Scopus citations

Abstract

Metalated and free-base A 3B-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.

Original languageEnglish (US)
Pages (from-to)14900-14909
Number of pages10
JournalLangmuir
Volume27
Issue number24
DOIs
StatePublished - Dec 20 2011

ASJC Scopus subject areas

  • Materials Science(all)
  • Condensed Matter Physics
  • Surfaces and Interfaces
  • Spectroscopy
  • Electrochemistry

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