Quinoline-fused BODIPY with large Stokes shift as near-infrared dye for cell imaging. (February 2020)

• Record Type: Journal Article
• Authors: Liu, Ying; Yang, Liutao; Ma, Chunping; Tang, Anjiang
• Is Part Of: Dyes and pigments. Volume 173(2020)
• Publication Date: 2020-02
• Subjects: BODIPY -- Quinoline -- Stokes shift -- Red shift -- Cell imaging; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2019.107981
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: A new BODIPY dye was synthesized by fusing quinoline with BODIPY core by oxidative cyclodehydrogenation reaction, and the spectral properties of this dye were investigated. It displayed remarkable red shift in absorption and emission spectra compared with its precursor. Especially, the maximum emission peak of the fused dye reached to the near-infrared region. The red-shifted spectrum was ascribed to the expansion of molecular electron system. Meanwhile, due to the reduction of molecular symmetry, the quantum yield of the fused dye in dichloromethane was 41% and Stokes shift was 67 nm. Moreover, the results of cell imaging showed that the fused dye could be a candidate chromophore in organisms due to its good imaging effect, high photostability and low cytotoxicity. In addition, the fused dye exhibited a quantum yield of 0.12 in solid state. Highlights: The quinoline-fused BODIPY exhibits significant bathochromic shift. The BODIPY dye exhibits an enlarged Stokes shift of 67 nm in CH2 Cl2 . The BODIPY dye can be used to image living cells. The BODIPY dye shows solid-state fluorescence.