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Quasi-One-Dimensional Electronic Systems Formed from Boron Dipyrromethene (BODIPY) Dyes

Lookup NU author(s): Emeritus Professor Anthony Harriman

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Abstract

Synthetic strategies have been devised that allow the rational design and isolation of highly coloured boron dipyrromethene (BODIPY) dyes that absorb across much of the visible region. Each dye has an aryl polycycle (usually pyrene or perylene) connected to the central BODIPY core through a conjugated tether at the 3,5-positions. Both mono- and difunctionalised derivatives are accessible, in certain cases containing both pyrene and perylene residues. For all new compounds, the photophysical properties have been recorded in solution at ambient temperature and in a glassy matrix at 77 K. The presence of the aryl polycycle(s) affects the absorption and emission maxima of the BODIPY nucleus, thereby confirming that these units are coupled electronically. Indeed, the band maxima and oscillator strengths depend on the conjugation length of the entire molecule, whereas there is no sign of fluorescence from the polycycle. As a consequence, the radiative rate constant tends to increase with each added appendage. The nature of the linkage (styryl, ethenyl, or ethynyl) also exerts an effect on the photophysical properties and, in particular, the absorption spectrum is perturbed in the region of the aryl polycycle. The perylene-containing BODIPY derivatives absorb over a wide spectral range and emit in the farred region in almost quantitative yield. A notable exception to this generic behaviour is provided by the anthracenyl derivative, which exhibits charge-transfer absorption and emission spectra in weakly polar media at ambient temperature. Regular BODIPY-like behaviour is restored in a glassy matrix at 77 K. Overall, these new dyes represent an important addition to the range of strongly absorbing and emitting reagents that could be used as solar concentrators.

Publication metadata

Author(s): Ziessel R, Rihn S, Harriman A

Publication type: Article

Publication status: Published

Journal: Chemistry: A European Journal

Year: 2010

Volume: 16

Issue: 39

Pages: 11942-11953

Print publication date: 01/01/2010

ISSN (print): 1521-3765

ISSN (electronic): 1521-3765

Publisher: Wiley-Blackwell Publishing

URL: http://dx.doi.org/10.1002/chem.201001142

DOI: 10.1002/chem.201001142

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