Design and Development of Axially Chiral Bis(naphthofuran) Luminogens as Fluorescent Probes for Cell Imaging
Valmik P. Jejurkar, Gauravi Yashwantrao, Pawan Kumar, Suditi Neekhra, Parimal J. Maliekal, Purav M. Badani, Rohit Srivastava, Satyajit Saha
Abstract
Designing chiral AIEgens without aggregation-induced emission (AIE)-active molecules externally tagged to the chiral scaffold remains a long-standing challenge for the scientific community. The inherent aggregation-caused quenching phenomenon associated with the axially chiral (R)-[1,1'-binaphthalene]-2,2'-diol ((R)-BINOL) scaffold, together with its marginal Stokes shift, limits its application as a chiral AIE-active material. Here, in our effort to design chiral luminogens, we have developed a design strategy in which 2-substituted furans, when appropriately fused with the BINOL scaffold, will generate solid-state emissive materials with high thermal and photostability as well as colour-tunable properties. The excellent biocompatibility, together with the high fluorescence quantum yield and large Stokes shift, of one of the luminogens stimulated us to investigate its cell-imaging potential. The luminogen was observed to be well internalised and uniformly dispersed within the cytoplasm of MDA-MB-231 cancer cells, showing high fluorescence intensity.