2-Acyl-1-aryl-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole derivatives: Versatile fluorescent probes with remarkably large Stokes shift


Dyes and Pigments

Nejc Petek, Bibi Erjavec, Dejan Slapšak, Aljaž Gaber, Uroš Grošelj, Franc Požgan, Sebastijan Ričko, Bogdan Štefane, Marina Klemenčič, Jurij Svete

A series of thirteen 2-acyl-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole derivatives were synthesized by using a copper-catalyzed azomethine-imine-alkyne cycloaddition as a key step. These bimane-related fluorescent compounds with λex = 338–400 nm and λem = 522–644 nm exhibit interesting and promising optical properties, including a remarkably large Stokes shift (150–268 nm), positive solvatochromism, and strong dependence of emission intensity on pH in a range of pH 2–10. The benzotriazolide- and N-succinimidyl ester-functionalized compounds were successfully used as fluorescent probes for protein labelling.

Read article: Dyes Pigm., 2022, 201, 110224