title: Dithienylcyclopentene-functionalised subphthalocyaninatoboron complexes: photochromism, luminescence modulation and formation of self-assembled monolayers on gold.
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.
authors.affiliation: National ESCA and Surface Analysis Center for Biomedical Problems (NESAC/BIO), Department of Bioengineering, University of Washington, Seattle, Washington 98195, USA.
authors.forename: Tobias
authors.initials: T
authors.lastname: Weidner
authors.forename: Joe E
authors.initials: JE
authors.lastname: Baio
authors.forename: Johannes
authors.initials: J
authors.lastname: Seibel
authors.forename: Ulrich
authors.initials: U
authors.lastname: Siemeling
mesh_terms: D001896:Boron Compounds / Q000737:chemistry*; D003517:Cyclopentanes / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D054833:Isoindoles; D049449:Luminescence; D010084:Oxidation-Reduction; D055668:Photochemical Processes; D056951:Photoelectron Spectroscopy; D013056:Spectrophotometry, Ultraviolet
chemical_list: C517933:1,2-dithienylcyclopentene; D001896:Boron Compounds; D003517:Cyclopentanes; D007211:Indoles; D054833:Isoindoles; D006046:Gold; C013647:phthalocyanine