Dithienylcyclopentene-functionalised subphthalocyaninatoboron complexes: Photochromism, luminescence modulation and formation of self-assembled monolayers on gold

Tobias Weidner, Joe E. Baio, Johannes Seibel, Ulrich Siemeling

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaperJournal articleResearchpeer-review

Abstract

Subphthalocyaninatoboron (SubPc) complexes bearing six peripheral n-dodecylthio substituents and an apical photochromic dithienylperfluorocyclopentene unit were prepared. The photoinduced isomerisation of the apical substituent from the open to the ring-closed form significantly influences the photoluminescence of the covalently attached SubPc unit, which is more efficiently quenched by the ring-closed form. Films on gold were fabricated from these multifunctional conjugates and characterised by near-edge X-ray absorption fine structure (NEXAFS) and X-ray photoelectron spectroscopy (XPS). The results are in accord with the formation of self-assembled monolayers based on dome-shaped SubPc-based anchor groups. Their chemisorption is primarily due to the peripheral n-dodecylthio substituents, giving rise to covalently attached thiolate as well as coordinatively bound thioether units, whose alkyl chains are in an almost parallel orientation to the surface.

Original languageEnglish
JournalDalton Transactions (Print Edition)
Volume41
Issue5
Pages (from-to)1553-1561
Number of pages9
ISSN1477-9226
DOIs
Publication statusPublished - 2012
Externally publishedYes

Keywords

  • Boron Compounds
  • Cyclopentanes
  • Gold
  • Indoles
  • Luminescence
  • Oxidation-Reduction
  • Photochemical Processes
  • Photoelectron Spectroscopy
  • Spectrophotometry, Ultraviolet
  • Journal Article
  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

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