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Charge-Recombination Fluorescence from Push-Pull Electronic Systems Constructed around Amino-Substituted Styryl-BODIPY Dyes

Lookup NU author(s): Patrycja Stachelek, Emeritus Professor Anthony Harriman

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Abstract

A small series of donor-acceptor molecular dyads has been synthesized and fully characterized. In each case, the acceptor is a dicyanovinyl unit and the donor is a boron dipyrromethene (BODIPY) dye equipped with a single styryl arm bearing a terminal amino group. In the absence of the acceptor, the BODIPY-based dyes are strongly fluorescent in the far-red region and the relaxed excited-singlet states possess significant charge-transfer character. As such, the emission maxima depend on both the solvent polarity and temperature. With the corresponding push-pull molecules, there is a low-energy charge-transfer state that can be observed by both absorption and emission spectroscopy. Here, charge-recombination fluorescence is weak and decays over a few hundred picoseconds or so to recover the ground state. Overall, these results permit evaluation of the factors affecting the probability of charge-recombination fluorescence in push-pull dyes. The photophysical studies are supported by cyclic voltammetry and DFT calculations.

Publication metadata

Author(s): Nano A, Ziessel R, Stachelek P, Harriman A

Publication type: Article

Publication status: Published

Journal: Chemistry - A European Journal

Year: 2013

Volume: 19

Issue: 40

Pages: 13528-13537

Print publication date: 01/09/2013

Online publication date: 14/08/2013

Acceptance date: 14/06/2013

ISSN (print): 0947-6539

ISSN (electronic): 1521-3765

Publisher: Wiley - VCH Verlag GmbH & Co. KGaA

URL: http://dx.doi.org/10.1002/chem.201301045

DOI: 10.1002/chem.201301045

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