Tetraphenylpyrene has been selected as a discotic core to promote liquid-crystalline fluorescent columns in view of its high fluorescence quantum yield in solution and ease of substitution by flexible lateral side chains. The synthesis and characterization of ten new derivatives of pyrene have been carried out; the pyrene core has been substituted at the 1,3,6,8-positions by phenylene rings bearing alkoxy, ester, thioether, or tris(alkoxy)benzoate groups on the para position; the compounds have been characterized by mass spectrometry and ¹H NMR and UV-vis spectroscopies. In order to generate liquid-crystalline phases, the nature, number, and size of the side chains as well as the degree of polarity around the tetraphenylpyrene core have been varied. However, the desired liquid-crystalline behavior has not been observed. The supramolecular order together with the absorption and emission properties in solution and the solid state are discussed and compared to theoretical predictions. Quantum-chemical calculations rationalize the high solid-state fluorescence of a tetraphenylpyrene derivative for which the crystal structure has been determined.

中文翻译：

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1,3,6,8-四苯基py衍生物：转向荧光液晶柱？^†

考虑到四苯基py在溶液中的高荧光量子产率以及易于被柔性侧链取代，因此已被选为促进液晶荧光柱的盘状核。已经进行了十种新的derivatives衍生物的合成和表征。芘核已在由亚苯基环的1,3,6,8-位轴承烷氧基，酯被置换，硫醚，或在三（烷氧基）苯甲酸甲酯基对位位置; 该化合物已通过质谱进行了表征，并且¹1 H NMR和UV-可见光谱。为了产生液晶相，已改变了侧链的性质，数量和大小以及四苯基py核周围的极性程度。但是，尚未观察到期望的液晶行为。讨论了超分子顺序以及溶液和固态中的吸收和发射性质，并将其与理论预测进行了比较。量子化学计算合理化了已确定晶体结构的四苯基fluorescence衍生物的高固态荧光。