Department of Chemistry, Seoul National University, Seoul 151-747, Korea.
J Am Chem Soc. 2011 May 4;133(17):6642-9. doi: 10.1021/ja110766a. Epub 2011 Apr 12.
In this paper we report on a novel fluorescent core skeleton, 9-aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one, which we named Seoul-Fluor, having tunable and predictable photophysical properties. Using a concise and practical one-pot synthetic procedure, a 68-member library of new fluorescent compounds was synthesized with diverse substituents. In Seoul-Fluor, the electronic characteristics of the substituents, as well as their positional changes, have a close correlation with their photophysical properties. The systematic perturbation of electronic densities on the specific positions of Seoul-Fluor, guided with the Hammett constant, allows emission wavelength tunability covering the full color range. On the basis of these observations and a computational analysis, we extracted a simple first-order correlation of photophysical properties with the theoretical calculation and accurately predicted the emission wavelength of Seoul-Fluors through the rational design. In this study, we clearly demonstrate that Seoul-Fluor can provide a powerful gateway for the generation of desired fluorescent probes without the need for a tiresome synthesis and trial-and-error process.
本文报道了一种新型荧光核心骨架，9-芳基-1,2-二氢吡咯并[3,4-b]吲哚啉-3-酮，我们将其命名为 Seoul-Fluor，它具有可调节和可预测的光物理性质。通过简洁实用的一锅合成方法，用各种取代基合成了一个包含 68 个新荧光化合物的文库。在 Seoul-Fluor 中，取代基的电子特性以及它们的位置变化与光物理性质密切相关。通过哈米特常数引导，对 Seoul-Fluor 特定位置的电子密度进行系统的扰动，可以实现覆盖整个颜色范围的发射波长调谐。基于这些观察和计算分析，我们提取了光物理性质与理论计算的简单一阶相关性，并通过合理设计准确预测了 Seoul-Fluors 的发射波长。在这项研究中，我们清楚地表明，Seoul-Fluor 可以为生成所需的荧光探针提供强大的途径，而无需繁琐的合成和反复试验过程。
