Synthesis, spectroscopic characterization, one and two-photon absorption properties and electrochemistry of π-expanded BODIPYs dyes

Monostyryl and distyryl substituted BODIPY derivatives were synthesized by the Knoevenagel condensation reaction and fully characterized by 1H NMR and HRMS. Their photophysical and electrochemical properties have been investigated by UV–vis absorption spectroscopy, steady-state and time-resolved flu...

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Bibliographic Details
Published in:Dyes and pigments 2020-04, Vol.175, Article 108173
Main Authors: Yang, Jian, Cai, Fangjian, Desbois, Nicolas, Huang, Laihai, Gros, Claude P., Bolze, Frédéric, Fang, Yuanyuan, Wang, Shifa, Xu, Hai-Jun
Format: Article
Language:English
Subjects:
BODIPY
Electrochemistry
Photophysical properties
Synthesis
Two-photon absorption
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Summary:Monostyryl and distyryl substituted BODIPY derivatives were synthesized by the Knoevenagel condensation reaction and fully characterized by 1H NMR and HRMS. Their photophysical and electrochemical properties have been investigated by UV–vis absorption spectroscopy, steady-state and time-resolved fluorescence spectroscopy, two-photon excited spectroscopy and cyclic voltammetry. These BODIPY dyes exhibit excellent photophysical properties in red to near-infrared region, including large extinction coefficients, high fluorescence quantum yields. They also exhibit high two-photon absorption cross sections in the 750–900 nm range. In particular, 3c presents a maximum with a σ2 of 2130 GM in the 750–900 nm range. In addition, the absorption and steady-state fluorescence properties in different solvents were investigated. Compounds 2b and 3b show significant positive solvatochromic fluorescence in organic solvents due to their intramolecular charge-transfer (ICT) from the aniline moiety to the BODIPY unit. All the investigated compounds undergo ring centered electron transfer by first oxidation and first reduction to generate cation and anion radicals. Mono- and distyril-BODIPY dyes exhibit high two-photon absorption cross section in the 750–900 nm range. [Display omitted] •Eight mono- and di-styryl substituted BODIPY derivatives were developed.•One- and two-photon photophysical characterizations were performed.•3c shows brightness up to 100 000 M−1 and two-photon absorption cross sections up to 2130 GM.
ISSN:0143-7208
1873-3743
DOI:10.1016/j.dyepig.2019.108173