Dithienylcyclopentene-functionalised subphthalocyaninatoboron complexes: photochromism, luminescence modulation and formation of self-assembled monolayers on gold |
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Authors: | Weidner Tobias Baio Joe E Seibel Johannes Siemeling Ulrich |
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Affiliation: | National ESCA and Surface Analysis Center for Biomedical Problems (NESAC/BIO), Department of Bioengineering, University of Washington, Seattle, Washington 98195, USA. |
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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. |
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