Investigation of the structural, optical, and electrochemical properties of a BODIPY system functionalized with carbazole and bromine moieties


ÖZDEMİR M.

Inorganic Chemistry Communications, cilt.182, 2025 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 182
  • Basım Tarihi: 2025
  • Doi Numarası: 10.1016/j.inoche.2025.115516
  • Dergi Adı: Inorganic Chemistry Communications
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, DIALNET
  • Anahtar Kelimeler: BODIPY, Carbazole, Energy transfer, Physicochemical properties, Synthesis
  • Marmara Üniversitesi Adresli: Evet

Özet

In this study, a novel tetrabromo-substituted BODIPY derivative containing a carbazole unit (Br4-CB) was synthesized, and its structural, photophysical, and electrochemical properties were thoroughly investigated. Single-crystal X-ray diffraction analysis revealed a molecular architecture stabilized by halogen–halogen interactions, featuring extended π-conjugation and pronounced intermolecular π–π stacking. Optical measurements conducted in various solvents showed strong absorption and emission characteristics, high fluorescence quantum yields reaching up to 0.98 in hexane, and significant solvent-dependent Stokes shifts. Br4-CB exhibited a singlet oxygen quantum yield (ΦΔ) of 0.50 in DMSO. Furthermore, efficient energy transfer from the carbazole moiety to the BODIPY core was observed in DCM, as confirmed by fluorescence measurements, accompanied by a notably prolonged fluorescence lifetime compared to other solvents (τ = 12.9 ns). Electrochemical analyses and DFT calculations revealed consistent HOMO-LUMO energy levels and a narrow bandgap (Egap = 1.37–1.40 eV), highlighting the compound's potential as a semiconducting material. Overall, the synergistic effect of the carbazole and bromine functionalities effectively modulates the physicochemical behavior of the BODIPY framework, positioning Br4-CB as a promising core structure for light-harvesting applications.