Imidazole decorated dicyanomethylene-4H-pyran skeletons with aggregation induced emission effect and applications for sensing viscosity. (September 2021)

• Record Type: Journal Article
• Authors: Li, Qi; Huang, Kun; Qiu, Qi; Zhang, Xiangyu; Qin, Dabin; Zeng, Xianshun
• Is Part Of: Dyes and pigments. Volume 193(2021)
• Publication Date: 2021-09
• Subjects: Fluorescence -- AIE -- Viscosity; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2021.109537
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: Two imidazole decorated 4-dicyanomethylene-2, 6-dimethyl-4H-pyran (DCM) derivatives, namely ImDCM-1 and ImDCM-2, have been designed and synthesized, which show aggregation-induced emission (AIE) features in THF-water mixture due to inhibition of intramolecular rotation (water fractions 80% and 70% for ImDCM-1 and ImDCM-2, respectively). The further increasing water leads to fluorescence bathochromic-shift and enhancement of ImDCM-1, probably arising from variation in size and solubility of aggregates. In contrast, ImDCM-2 exhibits a distinct red-shift and further enhancement in emission with water fraction increasing from 70% to 80%, then the further increment of water induces decrease in emission, which may be ascribed to formation of J-aggregates, followed by size and solubility changes of aggregates. In addition, selective and sensitive fluorescence responses of ImDCM-1 and ImDCM-2 towards viscosity can be observed. Significantly, the low cell cytotoxicity as well as wide pH-independence (4.0–10.0) fluorescent response towards viscosity allow them to be utilized for tracing monensin-stimulated viscosity increase in living cells. Highlights: Two imidazole decorated dyes with aggregation-induced emission behaviors have been reported. Viscosity-selective and sensitive fluorescence response can be observed. Tracing monensin-stimulated cellular viscosity increase by cell imaging can be realized.