Visible light-emitting fluorescent organic compounds are extensively used tools in microscopy for the precise tracking of specific molecules in biological systems. Unfortunately, most of the commonly employed fluorescent cores suffer from a narrow variability of the absorption and emission waveleghts, and the effect of substitutents on these wavelengths are often difficult to predict. This presentation reports the discovery of a previously unknown tetracyclic structure with interesting photochemical properties. These benzo[a]imidazo[2,1,5-cd]indolizines are readily functionalized in a divergent synthetic pathway to yield a library of fluorescent probes with emission wavelengths covering the entire visible spectrum. DFT calculations are able to rationalize and predict these compounds' photochemical properties, allowing the precise tuning of these properties by selecting the functional groups attached to the core. Various reactive functional groups can be attached to the core without affecting photochemical properties, enabling the tethering of the fluorophore to biomolecules. Their high absorption wavelengths, chemical stability and conjugation also open the door for potential applications in dye-sensitized solar cells.

Benzo[a]imidazo[2,1,5-cd]indolizines as tunable heterocyclic fluorophores: Synthesis and applications

249th National Meeting (2015)

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