Synthesis, chemiluminescence and energy transfer efficiency of 2,3-dihydrophthalazine-1,4-dione and BODIPY dyad

The design, synthesis and energy transfer efficiency of a new covalently linked molecular dyad 5, which consists of 2,3-dihydrophthalazine-1,4-dione and BODIPY scaffolds, are reported. It is noteworthy that dyad 5 can induce chemiluminescence upon treatment with alkaline H2O2 in the presence of Fe(III) ions. This reaction triggers chemiluminescence resonance energy transfer (CRET) from 2,3-dihydrophthalazine-1,4-dione unit to BODIPY fluorophore, which act as the donor and the acceptor components, respectively. To our best knowledge, this is the first example of a covalently linked molecular dyad consisting of chemiluminogenic 2,3-dihydrophthalazine-1,4-dione and BODIPY dye. Importantly, dyad 5 can provide a low energy emitting material via the chemiluminescence energy transfer (CRET), which covers almost the entire visible region (400 nm-700 nm) of the electromagnetic spectrum. (C) 2017 Elsevier Ltd. All rights reserved.