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

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

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alternative:
New Dyes Based on Extended Fulvene Motifs: Synthesis through Redox Reactions of Naphthoquinones with Donor-Acceptor Cyclopropanes and Their Spectroelectrochemical Behavior.
Original:
Chemistry Vol. 25 Iss. 44, S. 10359 - 10365.
(2019)
Date Issued:
2019
URN:
urn:nbn:de:gbv:084-2020022614107
DOI:
10.24355/dbbs.084-202002261404-0
Other identifier (pubmed):
31106926
Language:
English
Type of Resource:
Text
Extent:
7 Seiten
Publisher:
Wiley
Keywords:
  1. Dyes
    Typ
    Schlagwort
  1. Spectroelectrochemistry
    Typ
    Schlagwort
  1. Epr Spectroscopy
    Typ
    Schlagwort
  1. Fulvene
    Typ
    Schlagwort
  1. Donor-acceptor Cyclopropanes
    Typ
    Schlagwort
DDC:
547 Organische Chemie
Location:
Publications of TU Braunschweig
Link to Raw Object:
https://doi.org/10.1002/chem.201900764
Hosting institution:
02 - Life Sciences
Comment:
Im Original erschienen unter dem Titel: New Dyes Based on Extended Fulvene Motifs: Synthesis through Redox Reactions of Naphthoquinones with Donor–Acceptor Cyclopropanes and Their Spectroelectrochemical Behavior

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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.

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