One-pot chemoselective domino condensation to form a fused pyrrolo–pyrazino–indolizine framework: discovery of novel AIE molecules?

Organic Chemistry Frontiers Pub Date: 2020-03-31 DOI: 10.1039/D0QO00274G

Abstract

Luminogens with AIE (aggregation-induced emission) properties have been rapidly developed and are widely applied in many fields, such as solar cell research, biosensor study and bio-imaging advancement. It remains highly desirable to acquire new AIE molecules with excellent luminescence characteristics through facile, rapid, and efficient synthesis. Here, a chemoselective domino condensation to form highly fused pyrrolo[1′,2′:1,6]pyrazino[2,3-g]indolizines (5-6-6-5) was developed using N-substituted pyrrole-2-carbaldehydes and pyrrole-2-carbonitriles. The resultant products showed good AIE properties, exhibiting strong yellow fluorescence at up to 571 nm with a large Stokes shift (170 nm). Further live cell imaging and biocompatibility studies suggested that these products may find potential applications in various biomedical fields.

Graphical abstract: One-pot chemoselective domino condensation to form a fused pyrrolo–pyrazino–indolizine framework: discovery of novel AIE molecules
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