Molecular fluorescence is a rapidly growing research field that provides an outstanding tool for nondestructive investigations in biology, biomedical science, environment and drug discovery. Moreover, there is high demand of fluorescent materials in electronic and energy industry for applications in OLED (organic light-emitting diode) and organic solar cell. Accordingly, we have witnessed remarkable advances in these fields over the last several decades and we have now an access to a variety of fluorescent scaffolds, which are commonly outsourced as the prototypes to design new fluorophores. In this poster, we describe a synthetic method for the access to a series of fluorescent thieno[3,2-b]pyridine-5(4H)-one derivatives via a gold(I)-catalyzed 6-endo-dig cycloisomerization of Nthiophen-3-yl alkynylamides. Investigation on the photophysical properties of the newly synthesized fluorophores revealed that the photophysical properties are chemically tunable by an appropriate choice of functional group on the thieno[3,2-b]pyridine-5(4H)-one scaffold (emission maxima up to 559 nm, Stokes shifts up to 197 nm, and quantum yields up to 98%). Next, our endeavor aimed at establishing a small-molecule fluorescent probe for vimentin is described which is based on the conjugate of withaferin A (a natural product originally derived from Withania somnifera) and a fluorescent thieno[3,2-b]pyridine-5(4H)-one derivative. Vimentin is an intermediate filament (IF) protein which is highly expressed in mesenchymally-derived cells or cells undergoing EMT (epithelial-mesenchymal transition). This approach would provide an attractive starting point to enable a tailor-made function into a molecule of choice for non-destructive investigations in various research areas.

Gold(I)-catalyzed synthesis of 2-arylthieno[3,2-b]pyridine-5(4H)-ones and studies toward a small-molecule fluorescent probe for vimentin

256th National Meeting (2018)

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