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New Dyes Based on Extended Fulvene Motifs: Synthesis through Redox Reactions of Naphthoquinones with Donor–Acceptor Cyclopropanes and Their Spectroelectrochemical Behavior
Author(s) -
Lücht Alexander,
Sobottka Sebastian,
Patalag Lukas J.,
Jones Peter G.,
Reissig HansUlrich,
Sarkar Biprajit,
Werz Daniel B.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900764
Subject(s) - fulvene , chemistry , photochemistry , electrochromism , redox , electrochemistry , trifluoromethanesulfonate , acceptor , nucleophile , combinatorial chemistry , organic chemistry , catalysis , electrode , physics , condensed matter physics
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.