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Spermine-Functionalized Perylene Bisimide Dyes-Highly Fluorescent Bola-Amphiphiles in Water

机译:精胺功能的Per双酰亚胺染料-水中的高荧光波拉两亲物

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A series of four spermine-functionalized perylene bisimide dyes without linkers (1) and with linkers (2-4) between the chromophore and the polyamine was synthesized. Protonation of the spermine moieties resulted in the formation of highly water-soluble dyes with up to six positively charged ammonium ions. The aggregation behavior of these strongly fluorescent bola-amphiphiles was studied in pure water as solvent by UV/Vis and fluorescence spectroscopy, and an astonishingly high fluorescence quantum yield of up to Phi(fl) = 0.90 was observed for PBI 1. Atomic force microscopy and transmission electron microscopy were applied for the visualization of the aggregates on surfaces. Molecular modeling studies were performed by force-field calculations to explore the aggregate morphologies, which also provided valuable information on the influence of the additional alkylcarbonyl linkers. Our detailed spectroscopic and microscopic investigations revealed that the excellent optical properties of perylene bisimide chromophores can be used even in pure deionized water if their aggregation is efficiently suppressed.
机译:合成了一系列的四种精胺官能化的bi双酰亚胺染料,它们在生色团和多胺之间没有接头(1),而接头(2-4)。精胺部分的质子化导致形成高度水溶性的染料,该染料最多具有六个带正电的铵离子。通过UV / Vis和荧光光谱研究了这些强荧光的两亲物在纯水中作为溶剂的聚集行为,并且在PBI 1上观察到惊人的高荧光量子产率,最高可达Phi(fl)= 0.90。透射电镜和透射电子显微镜用于表面聚集体的可视化。通过力场计算进行分子建模研究以探索聚集体形态,这也提供了有关其他烷基羰基连接基影响的有价值的信息。我们的详细光谱和显微镜研究表明,如果有效抑制了aggregation双酰亚胺发色团的聚集,即使在纯去离子水中也可以使用其优异的光学性能。

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