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Synthesis, spectroscopic characterization, one and two-photon absorption properties and electrochemistry of π-expanded BODIPYs dyes
Dyes and Pigments ( IF 4.1 ) Pub Date : 2019-12-27 , DOI: 10.1016/j.dyepig.2019.108173
Jian Yang , Fangjian Cai , Nicolas Desbois , Laihai Huang , Claude P. Gros , Frédéric Bolze , Yuanyuan Fang , Shifa Wang , Hai-Jun Xu

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.



中文翻译:

π膨胀BODIPYs染料的合成,光谱表征,一,二光子吸收特性和电化学。

单苯乙烯基和二苯乙烯基取代的BODIPY衍生物是通过Knoevenagel缩合反应合成的,并通过1 H NMR和HRMS进行了全面表征。通过紫外可见吸收光谱,稳态和时间分辨荧光光谱,双光子激发光谱和循环伏安法研究了它们的光物理和电化学性质。这些BODIPY染料在红色至近红外区域具有出色的光物理性质,包括大的消光系数和高的荧光量子产率。它们还表现出在750-900 nm范围内的高双光子吸收截面。特别地,图3c显示一个带有一个最大σ 2在750–900 nm范围内的2130 GM分布。此外,还研究了在不同溶剂中的吸收和稳态荧光性质。由于化合物2b3b从苯胺部分到BODIPY单元的分子内电荷转移(ICT),在有机溶剂中显示出显着的正溶剂化变色荧光。所有被研究的化合物都通过先氧化和先还原以产生阳离子和阴离子自由基的方式进行以环为中心的电子转移。

更新日期:2019-12-27
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