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

Nano, Adela; Ziessel, Raymond; Stachelek, Patrycya; Harriman, Anthony

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.

Citation

Nano, A., Ziessel, R., Stachelek, P., & Harriman, A. (2013). Charge-Recombination Fluorescence from Push-Pull Electronic Systems Constructed around Amino-Substituted Styryl-BODIPY Dyes. Chemistry - A European Journal, 19(40), 13528-13537. https://doi.org/10.1002/chem.201301045

• Journal Article Type: Article
• Acceptance Date: Jun 16, 2013
• Online Publication Date: Aug 14, 2013
• Publication Date: Sep 27, 2013
• Deposit Date: Dec 7, 2020
• Journal: Chemistry - A European Journal
• Print ISSN: 0947-6539
• Electronic ISSN: 1521-3765
• Publisher: Wiley
• Volume: 19
• Issue: 40
• Pages: 13528-13537
• DOI: https://doi.org/10.1002/chem.201301045
• Public URL: https://durham-repository.worktribe.com/output/1249780