1-(Imidazol-1-yl)-indolizines—two-step synthesis and optical properties |
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Authors: | Rafał Matczak Beata Koszarna Daniel T Gryko |
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Institution: | 1. Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland;2. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland |
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Abstract: | A one-pot process leading to complex aromatic heterocyclic compounds has been designed. Kröhnke methodology has been used to synthesize indolizines bearing an aldimino-substituent at position 1. Further reaction of these compounds with 1,2-diketones and ammonium acetate led to tetra-substituted imidazoles in 5–28% overall yield. The resulting compounds display strong absorption of UV radiation and emission of a blue light accompanied with large Stokes shifts. Replacing the aryl substituents with thiophene at position 3 of the indolizine and position 2 of the imidazole produce a further red shift of the absorption (vs products with substituted benzene rings) as a result of a more planar conformation in the ground state. |
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Keywords: | Indolizine Fluorescence Heterocycles Imidazole Dyes |
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