Synthesis, spectroscopic characterization, one and two-photon absorption properties and electrochemistry of π-expanded BODIPYs dyes. (April 2020)

• Record Type: Journal Article
• Authors: Yang, Jian; Cai, Fangjian; Desbois, Nicolas; Huang, Laihai; Gros, Claude P.; Bolze, Frédéric; Fang, Yuanyuan; Wang, Shifa; Xu, Hai-Jun
• Is Part Of: Dyes and pigments. Volume 175(2020)
• Publication Date: 2020-04
• Subjects: BODIPY -- Two-photon absorption -- Photophysical properties -- Synthesis -- Electrochemistry; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2019.108173
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: Monostyryl and distyryl substituted BODIPY derivatives were synthesized by the Knoevenagel condensation reaction and fully characterized by 1 H 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 σ 2 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. Graphical abstract: Mono- and distyril-BODIPY dyes exhibit high two-photon absorption cross section in the 750–900 nm range. Image 1 Highlights: 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.