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

• Published in: Dyes and pigments Vol. 140; pp. 92 - 99
• Main Authors: Degirmenci, Aysun, Algi, Fatih
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01.05.2017
• Subjects: 2,3-dihydrophthalazine-1,4-dione; BODIPY; Chemiluminescence; CRET; Pyridazine; CRET; BODIPY; Chemiluminescence; 2,3-dihydrophthalazine-1,4-dione; Pyridazine
• ISSN: 0143-7208; 1873-3743
• DOI: 10.1016/j.dyepig.2017.01.037

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. [Display omitted] •2,3-dihydrophthalazine-1,4-dione and BODIPY dyad was synthesized and characterized.•Photophysical properties and energy transfer efficiency of this new dyad were investigated.•The new dyad induces chemiluminescence which was triggered by H2O2.•During chemiluminescence, energy transfer from 2,3-dihydrophthalazine-1,4-dione unit to BODIPY fluorophore takes place.•2,3-dihydrophthalazine-1,4-dione and BODIPY dyad exhibits bright-vivid white color as a result of chemiluminescence.