State Key Laboratory of Crystal Materials, Shandong University, Jinan, 250100, P. R. China.
School of Clinical and Basic Medical Sciences, Shandong First Medical University& Shandong Academy of Medical Sciences, Jinan, 250062, P. R. China.
Chem Asian J. 2023 Jun 1;18(11):e202300163. doi: 10.1002/asia.202300163. Epub 2023 May 2.
Developing halogen-functionalized fluorescent dyes with intriguing photophysical properties, including enhanced photostability, is particularly important for bioimaging. In this work, we synthesized two new halogen-functionalized aggregation-induced emission (AIE)-active molecules, DQMF-OH and DQMCl-OH, based on the quinoline-malononitrile chromophore. The halogen effect on the photophysical characteristics was detailedly studied by absorption and fluorescence spectroscopy, density functional theory calculations, and crystal structures. Compared with non-halogen substituted AIE luminogen (AIEgen) DQM-OH, the halogen substituted DQMF-OH and DQMCl-OH exhibited red-shifted absorptions and emissions in the solution and solid state. In addition, DQMF-OH and DQMCl-OH also possessed enhanced fluorescence toward viscosity changes. These AIEgens served as remarkable imaging tools for cell tracking in a wash-free manner. Furthermore, DQMF-OH and DQMCl-OH showed much more excellent photobleaching resistance than DQM-OH. Our work sheds new light on developing fluorescent halogenated dyes with enhanced photophysical performances for biological applications.
开发具有有趣光物理性质的卤代荧光染料，包括增强的光稳定性，对于生物成像尤为重要。在这项工作中，我们基于喹啉-马来腈生色团合成了两种新型卤代聚集诱导发射（AIE）活性分子 DQMF-OH 和 DQMCl-OH。通过吸收和荧光光谱、密度泛函理论计算和晶体结构详细研究了卤素对光物理特性的影响。与非卤代取代的 AIE 发光剂（AIEgen）DQM-OH 相比，卤代取代的 DQMF-OH 和 DQMCl-OH 在溶液和固态中表现出红移的吸收和发射。此外，DQMF-OH 和 DQMCl-OH 对粘度变化也表现出增强的荧光。这些 AIEgens 可用作无需洗涤的细胞跟踪的显著成像工具。此外，DQMF-OH 和 DQMCl-OH 的光漂白抗性比 DQM-OH 强得多。我们的工作为开发用于生物应用的具有增强光物理性能的荧光卤代染料提供了新的思路。
