A series of deep red fluorescent dyes: synthesis, theoretical calculations and bioimaging applications

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• 作者：Ming Zhang ; Xiaojing Liu ; Meipan Yang ; Shuting Zheng ; Yinjuan Bai ; Bing-qin Yang ; ^{yangbq@nwu.edu.cn" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Deep red fluorescent dyes ; Stokes shifts ; Biological imaging ; Cytotoxicity ; Theoretical calculations
• 刊名：Tetrahedron Letters
• 出版年：2015
• 出版时间：7 October 2015
• 年：2015
• 卷：56
• 期：41
• 页码：5681-5688
• 全文大小：2108 K

文摘

A series of deep red fluorescent dyes were synthesized and characterized. The optical properties, theoretical calculations, and cytotoxicity of these dyes were investigated. The practical applications of the dyes were also evaluated by fluorescence imaging in living cells. Compared to Rhodamine B (RB), the emission wavelengths of compounds 3a–e were extended to the deep red region (emission maximum ranging from 620 to 650 nm) in MeOH. Furthermore, compounds 3a–e exhibited wider Stokes shifts from 100 to 150 nm. We also performed time dependent density functional theory (TDDFT) theoretical calculations of 3a–e based on the density functional theory (DFT) optimized structures of the ground S₀ state and the first excited S₁ state. To test the application of these dyes, we constructed a new Hg²⁺ fluorescent probe T-2 based on 3d and evaluated its feasibility for fluorescence imaging in living cells. The results suggest that these novel deep red fluorescent dyes can be used a platform to construct fluorescent probes for bioimaging applications.