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首页> 外文期刊>The journal of physical chemistry, A. Molecules, spectroscopy, kinetics, environment, & general theory >Ratiometric, fluorescent BODIPY dye with aza crown ether functionality: Synthesis, solvatochromism, and metal ion complex formation
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Ratiometric, fluorescent BODIPY dye with aza crown ether functionality: Synthesis, solvatochromism, and metal ion complex formation

机译：具有氮杂冠醚功能的比例荧光BODIPY染料：合成，溶剂变色和金属离子配合物形成

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摘要

A new pH and metal ion-responsive BODIPY-based fluorescent probe with an aza crown ether subunit has been synthesized via condensation of 4-(1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-yl)-benzaldehyde with the appropriate 1,3,5,7-tetramethyl substituted boron dipyrromethene moiety. Steady-state and time-resolved fluorometries have been used to study the spectroscopic and photophysical characteristics of this probe in various solvents. The fluorescence properties of the dye are strongly solvent dependent: increasing the solvent polarity leads to lower fluorescence quantum yields and lifetimes, and the wavelength of maximum fluorescence emission shifts to the red. The Catalan solventscales are found to be the most suitable for describing the solvatochromic shifts of the fluorescence emission. Fluorescence decay profiles of the dye can be described by a single-exponential fit in nonprotic solvents, whereas two decay times are found in alcohols. Protonation as well as complex formation with several metal ions are investigated in acetonitrile as solvent via fluorometric titrations. The aza crown ether dye undergoes a reversible (de)protonation reaction (pKa = 0.09) and shows a similar to 50 nm blue shift in the excitation spectra and a 10-fold fluorescence increase upon protonation. The compound also forms 1:1 complexes with several metal ions (Li+, Na+, M2+, Ca2+ Ba2+ Zn2+), producing large blue shifts in the excitation spectra and significant cation-induced fluorescence amplifications.
机译：通过4-（1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-yl）-benzaldehyde的缩合反应合成了具有aza冠醚亚基的新型基于pH和金属离子的基于BODIPY的荧光探针具有适当的1,3,5,7-四甲基取代的硼二吡咯亚甲基部分。稳态和时间分辨荧光法已用于研究该探针在各种溶剂中的光谱和光物理特性。染料的荧光特性强烈依赖于溶剂：增加溶剂极性会导致较低的荧光量子产率和寿命，并且最大荧光发射的波长会变为红色。发现加泰罗尼亚溶剂垢最适合描述荧光发射的溶剂化变色。染料的荧光衰减曲线可以通过在非质子溶剂中的单指数拟合来描述，而在醇中发现两个衰减时间。通过荧光滴定法研究了乙腈作为溶剂的质子化以及与多种金属离子的络合物形成。氮杂冠醚染料经历了可逆的（去）质子化反应（pKa = 0.09），并且在激发光谱中显示出类似于50 nm的蓝移，并且在质子化时荧光增加了10倍。该化合物还与几种金属离子（Li +，Na +，M2 +，Ca2 + Ba2 + Zn2 +）形成1：1配合物，在激发光谱中产生大的蓝移并引起明显的阳离子诱导的荧光放大。

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