• Open Access

Fluorinated Boron-Dipyrromethene (BODIPY) Dyes: Bright and Versatile Probes for Surface Analysis

Authors

  • Mandy Hecht,

    1. Division 1.9 Sensor Materials, BAM Federal Institute for Materials Research and Testing, Richard-Willstätter-Str. 11, 12489 Berlin (Germany)
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  • Tobias Fischer,

    1. Division 1.9 Sensor Materials, BAM Federal Institute for Materials Research and Testing, Richard-Willstätter-Str. 11, 12489 Berlin (Germany)
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  • Dr. Paul Dietrich,

    1. Division 6.8 Surface Analysis and Interfacial Chemistry, BAM Federal Institute for Materials Research and Testing, Unter den Eichen 44–46, 12203 Berlin (Germany)
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  • Werner Kraus,

    1. Division 1.3 Structural Analysis, BAM Federal Institute for Materials Research and Testing, Richard-Willstätter-Str. 11, 12489 Berlin (Germany)
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  • Dr. Ana B. Descalzo,

    1. Division 1.9 Sensor Materials, BAM Federal Institute for Materials Research and Testing, Richard-Willstätter-Str. 11, 12489 Berlin (Germany)
    2. Current address: Department of Organic Chemistry, Faculty of Chemical Sciences, Complutense University of Madrid, Avda. Complutense s/n, 28040 Madrid (Spain)
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  • Dr. Wolfgang E. S. Unger,

    1. Division 6.8 Surface Analysis and Interfacial Chemistry, BAM Federal Institute for Materials Research and Testing, Unter den Eichen 44–46, 12203 Berlin (Germany)
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  • Dr. Knut Rurack

    Corresponding author
    1. Division 1.9 Sensor Materials, BAM Federal Institute for Materials Research and Testing, Richard-Willstätter-Str. 11, 12489 Berlin (Germany)
    • Division 1.9 Sensor Materials, BAM Federal Institute for Materials Research and Testing, Richard-Willstätter-Str. 11, 12489 Berlin (Germany)
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Abstract

A family of bright boron-dipyrromethene-type fluorophores with a high number of fluorine atoms (F-BODIPYs) has been developed and characterized by X-ray crystallography and optical spectroscopy. The introduction of 3,5-bis(trifluoromethyl)phenyl and pentafluorophenyl moieties significantly enhances the photostability of such dyes, yielding for instance photostable near-infrared (NIR) fluorophores that show emission maxima>750 nm, when the BODIPY’s π system is extended with two (dimethylamino)styryl and (dimethylamino)naphthastyryl moieties, or green-emitting BODIPYs with fluorescence quantum yields of unity. When equipped with a suitable group that selectively reacts for instance with amines, F-BODIPYs can be used as potent dual labels for the quantification of primary amino groups on surfaces by X-ray photoelectron spectroscopy (XPS) and fluorescence, two powerful yet complementary tools for the analysis of organic surface functional groups. The advantage of reactive F-BODIPYs is that they allow a fast and non-destructive mapping of the labelled supports with conventional fluorescence scanners and a subsequent quantification of selected areas of the same sample by the potentially traceable XPS technique. The performance is exemplarily shown here for the assessment of the amino group density on SiO2 supports, one of the most common reactive silica supports, in particular, for standard microarray applications.

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