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Scheme 2: Suzuki and Sonogashira cross-coupling reactions. It is interesting to note that compound 1 has the possibility to participate in an excited-state intramolecular proton transfer (ESIPT) process. The observed Stokes shift (1.00 x 10 -5 M, MeCN solution) was 194 nm (369 nm of absorption and 563 nm of emission). Derivatives 2a,b and 3a,b were directly applied in live cell-imaging experiments and presented promissory results (Figure 2).

Non-symmetrical benzothiadiazole derivatives live cell fluorescence imaging probes