Novel Benzothiophene-Based Fluorescent Dye Exhibiting a Large Stokes Shift

Abstract

We report a simple two-step method for the synthesis of a novel highly fluorescent benzothiophene-based dye comprising five fused rings and exhibiting a large Stokes shift (Δλ = 152 nm or Δν = 5482 cm–1 in ethanol). Structural features of the obtained compound allow easy functionalization of the carbon core and open new possibility for the development of a series of new classes of fluorescent dyes.

Total Synthesis of Racemic Thieno[3,2-f]thiochromene Tricarboxylate, a Luciferin from Marine Polychaeta Odontosyllis undecimdonta

“…Substituted benzothiophene 1 was obtained from 2,3-dimethoxybenzenethiol according to the method developed earlier in our group (Scheme ). Aromatic aldehydes are usually synthesized by the Vilsmeier–Haack reaction; however, preliminary experiments with DMF/POCl 3 or urotropine were unsuccessful, and we had to use an indirect approach toward intermediate 4 .…”