Layer-by-Layer Assemblies of Catechol-Functionalized TiO2 Nanoparticles and Porphyrins through Electrostatic Interactions

Alexandra Burger, Rubén D. Costa, Volodymyr Lobaz, Wolfgang Peukert, Dirk M. Guldi, Andreas Hirsch*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)


In the current work, we present the successful functionalization and stabilization of P-25 TiO2 nanoparticles by means of N1,N7-bis(3-(4-tert-butyl-pyridium-methyl)phenyl)-4-(3-(3-(4-tert-butyl-pyridinium-methyl)phenylamino)-3-oxopropyl)-4-(3,4-dihydroxybenzamido)heptanediamide tribromide (1). The design of the latter is aimed at nanoparticle functionalization and stabilization with organic building blocks. On one hand, 1 features a catechol anchor to enable its covalent grafting onto the TiO2 surface, and on the other hand, positively charged pyridine groups at its periphery to prevent TiO2 agglomeration through electrostatic repulsion. The success of functionalization and stabilization was corroborated by thermogravimetric analysis, dynamic light-scattering, and zeta potential measurements. As a complement to this, the formation of layer-by-layer assemblies, which are governed by electrostatic interactions, by alternate deposition of functionalized TiO2 nanoparticles and two negatively charged porphyrin derivatives, that is, 5,10,15,20-(phenoxyacetic acid)-porphyrin (2) and 5,10,15,20-(4-(2-ethoxycarbonyl)-4-(2-phenoxyacetamido)heptanedioic acid)-porphyrin (3), is documented. To this end, the layer-by-layer deposition is monitored by UV/Vis spectroscopy, scanning electron microscopy, ellipsometry, and profilometry techniques. The resulting assemblies are utilized for the construction and testing of novel solar cells. From stable and repeatable photocurrents generated during several "on-off" cycles of illumination, we derive monochromatic incident photo-to-current conversion efficiencies of around 3%.

Original languageEnglish
Pages (from-to)5041-5054
Number of pages14
JournalChemistry - A European Journal
Issue number13
Publication statusPublished - 2015 Mar 23
Externally publishedYes


  • catechol
  • layer-by-layer assemblies
  • nanoparticles
  • solar energy conversion
  • surface chemistry
  • surface functionalization

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry


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