Feedback

Novel Dyes Based on Extended Fulvene Motifs: Synthesis via Redox Reactions of Naphthoquinones with Donor‐Acceptor Cyclopropanes and Their Spectroelectrochemical Behavior

Affiliation
Technische Universität Braunschweig, Institut für Organische Chemie, Hagenring 30, 38106, Braunschweig, Germany.
Lücht, Alexander;
Affiliation
Institut für Chemie und Biochemie, Anorganische Chemie, Freie Universität Berlin, Fabeckstrasse 34-36, 14195, Berlin, Germany.
Sobottka, Sebastian;
ORCID
0000-0002-8956-1087
Affiliation
Technische Universität Braunschweig, Institut für Organische Chemie, Hagenring 30, 38106, Braunschweig, Germany.
Patalag, Lukas J;
Affiliation
Technische Universität Braunschweig, Institut für Anorganische und Analytische Chemie, Hagenring 30, 38106, Braunschweig, Germany.
Jones, Peter G;
ORCID
0000-0002-1912-9635
Affiliation
Institut für Chemie und Biochemie, Freie Universität Berlin, Takustrasse 3, 14195, Berlin, Germany.
Reissig, Hans-Ulrich;
ORCID
0000-0003-4887-7277
Affiliation
Institut für Chemie und Biochemie, Anorganische Chemie, Freie Universität Berlin, Fabeckstrasse 34-36, 14195, Berlin, Germany.
Sarkar, Biprajit;
ORCID
0000-0002-3973-2212
Affiliation
Technische Universität Braunschweig, Institut für Organische Chemie, Hagenring 30, 38106, Braunschweig, Germany.
Werz, Daniel B

Novel dyes based on extended fulvene motifs are reported. The carbon skeleton was generated by a catalyzed addition of donor-acceptor cyclopropanes to naphthoquinone. The hydroxy group at the central ring of the tricyclic fulvene motif was converted into the triflate, which reacted efficiently with a wide range of nucleophiles, resulting in substitution and thereby providing new derivatives. The synthetic versatility allowed us to investigate the absorption, electrochemical, and UV/Vis-NIR spectroelectrochemical properties of these dyes as a function of the substituents. The dyes were shown to participate in reductive electrochemistry, the reversibility of which can be improved by appropriate selection of the substituents. Additionally, first signs of NIR electrochromism are presented, opening new avenues for the future investigations of such dyes.

Cite

Citation style:
Could not load citation form.

Access Statistic

Total:
Downloads:
Abtractviews:
Last 12 Month:
Downloads:
Abtractviews:

Rights

License Holder: This is the peer reviewed version of the following article: New Dyes Based on Extended Fulvene Motifs: Synthesis through Redox Reactions of Naphthoquinones with Donor–Acceptor Cyclopropanes and Their Spectroelectrochemical Behavior, which has been published in final form at https://doi.org/10.1002/chem.201900764. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

Use and reproduction:
All rights reserved

Export