One-pot synthesis and applications of two asymmetrical benzoxanthene dyes

作者：Guo, Yimin; Wang, Xiuping; Liu, Weimin^*; Zheng, Xiuli; Ren, Haohui; Wu, Jiasheng; Ge, Jiechao; Zhang, Wenjun; Lee, Chun-Sing; Wang, Pengfei^*

来源：Dyes and Pigments, 2022, 200: 110152.

DOI：10.1016/j.dyepig.2022.110152

• Benzoxanthene dyes
• Near-infrared emission
• Photoinduced electron transfer
• Fluorescent imaging
• RNA dye

Two asymmetrical benzoxanthene dyes (BP-1 and BP-2) were designed and synthesized by a convenient one-step procedure from naphthaldehyde and m-aminophenol precursors. These dyes showed long-wavelength absorption, near-infrared emission (>650 nm), and large Stokes shifts (>90 nm) because of the asymmetrical introduction of the benzene ring into the xanthene structure. BP-1 exhibited high fluorescence quantum yield in organic solvents, whereas BP-2 showed very weak fluorescence due to the photoinduced electron transfer of 9 substituted groups. Cell experiments indicated that BP-1 with crescent-shape structure showed lower cytotoxicity and higher photostability than BP-2 and could rapidly stain RNA in nucleoli at low concentration.

• 单位
  中国科学院研究生院