Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany.
Chemistry. 2010 Mar 15;16(11):3372-82. doi: 10.1002/chem.200902839.
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.
合成了一系列不含连接子的四种 spermine 功能化的苝二酰亚胺染料（1）和含有发色团和多胺之间连接子的染料（2-4）。质子化 spermine 部分导致高度水溶性染料的形成，最多带有六个正电荷的铵离子。通过紫外/可见和荧光光谱研究这些强荧光两性分子在纯水中的聚集行为，发现 PBI1 的荧光量子产率高达 0.90。原子力显微镜和透射电子显微镜用于在表面上可视化聚集体。通过力场计算进行分子建模研究以探索聚集体形态，这也提供了有关附加烷基羰基连接子影响的有价值信息。我们详细的光谱和显微镜研究表明，如果有效抑制其聚集，即使在纯去离子水中也可以使用苝二酰亚胺发色团的优异光学性质。
