Synthesis and characterization of silicon phthalocyanines bearing axial phenoxyl groups for attachment to semiconducting metal oxides

Jesse J. Bergkamp, Benjamin D. Sherman, Ernesto Mariño-Ochoa, Rodrigo E. Palacios, Gonzalo Cosa, Thomas A Moore, John Devens Gust, Ana L Moore

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

A series of axial phenoxy substituted octabutoxy silicon phthalocyanines bearing ethyl carboxylic ester and diethyl phosphonate groups have been prepared from the corresponding phenols in pyridine. Axial bis-hydroxy silicon phthalocyanine was prepared using an adaptation of a reported protocol [1, 2] from the octabutoxy free-base phthalocyanine. The phenols bear either carboxylic ester or phosphonate groups, which upon deprotection can serve as anchoring groups for attaching the phthalocyanines to semiconducting metal oxides used in dye sensitized solar cells (DSSCs). All the phthalocyanines of the series absorb in the near infra-red region: 758-776 nm. The first oxidation potential for each phenoxy derivative occurs near 0.55 V vs. SCE as measured by cyclic voltammetry, with all falling within a 10 mV range. This indicates that these dyes will have sufficient energy in the photo-excited state to drive the reduction of protons to hydrogen. Taking into account the absorption and electrochemical potentials, these dyes are promising candidates for use in dual-threshold photo-electrochemical cells.

Original languageEnglish
Pages (from-to)943-950
Number of pages8
JournalJournal of Porphyrins and Phthalocyanines
Volume15
Issue number9-10
DOIs
Publication statusPublished - Sep 2011

Fingerprint

silicon phthalocyanine
Bearings (structural)
Oxides
Organophosphonates
Phenols
Metals
Esters
Coloring Agents
Photoelectrochemical cells
Excited states
Cyclic voltammetry
Protons
Hydrogen
Infrared radiation
Derivatives
Oxidation
phthalocyanine

Keywords

  • axial phenoxy linkage
  • electrochemistry
  • silicon phthalocyanines
  • synthesis

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis and characterization of silicon phthalocyanines bearing axial phenoxyl groups for attachment to semiconducting metal oxides. / Bergkamp, Jesse J.; Sherman, Benjamin D.; Mariño-Ochoa, Ernesto; Palacios, Rodrigo E.; Cosa, Gonzalo; Moore, Thomas A; Gust, John Devens; Moore, Ana L.

In: Journal of Porphyrins and Phthalocyanines, Vol. 15, No. 9-10, 09.2011, p. 943-950.

Research output: Contribution to journalArticle

Bergkamp, Jesse J. ; Sherman, Benjamin D. ; Mariño-Ochoa, Ernesto ; Palacios, Rodrigo E. ; Cosa, Gonzalo ; Moore, Thomas A ; Gust, John Devens ; Moore, Ana L. / Synthesis and characterization of silicon phthalocyanines bearing axial phenoxyl groups for attachment to semiconducting metal oxides. In: Journal of Porphyrins and Phthalocyanines. 2011 ; Vol. 15, No. 9-10. pp. 943-950.
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