Highly conjugated dibenzosuberenone-dihydropyridazine fluorophores: Design, synthesis and sensor properties
Journal of Molecular Liquids, cilt.453, 2026 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 453
- Basım Tarihi: 2026
- Doi Numarası: 10.1016/j.molliq.2026.129489
- Dergi Adı: Journal of Molecular Liquids
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, Chimica, Compendex, INSPEC
- Anahtar Kelimeler: Dibenzosuberenone, Dihydropyridazine, Heavy metal, IEDDA, Multifunctional sensor
- Atatürk Üniversitesi Adresli: Evet
Özet
In this study, four structurally novel π-conjugated small organic molecules having a dibenzosuberenone-dihydropyridazine (DD) core were synthesized through a multistep synthetic strateğy involving sequential bromination, Pd-catalyzed Suzuki coupling reactions, and an inverse electron-demand Diels–Alder (IEDDA) cycloaddition. The synthetic route commenced with the preparation of a versatile intermediate, dibromodibenzosuberenone 1 , which was followed by structural diversification via Suzuki coupling with a range of heteroaryl boronic acid and boronic ester derivatives ( 2a-2d ). In the final step, cycloaddition with a tetrazine derivative DPT 4 afforded target dibenzosuberenone-dihydropyridazine derivatives DD1-DD4 , featuring extended π-conjugation and heteroatom-rich architectures that have not been previously reported. All intermediates and target molecules were purified and fully characterized using 1H NMR, 13C NMR, FTIR, and HRMS techniques. The photophysical properties of the synthesized compounds were systematically investigated, along with their sensing performances toward heavy metal ions, multiple metal ions, and multi-analyte systems. The sensing behaviors of the fluorophores, DD1-DD4 , were investigated by UV–Vis and fluorescence spectroscopies in the presence of a wide range of mono-, di-, and trivalent cations. The compounds exhibit a pronounced ability to recognize Pb2+ ion as well as Cd2+ and Cr3+ ions. Moreover, counter ion studies conducted for DD1 revealed a decreasing emission intensity toward I− and CN− anions. In line with these noteworthy findings, the design and synthesis of dibenzosuberenone–dihydropyridazine-based molecules highlight their potential for novel optical and sensing applications.