Synthesis and photophysical properties of monomeric and dimeric halogenated aza-BODIPYs

Çınar H. Ş., Özçelik Ş., Kaya K., Kutlu Ö., Erdoğmuş A., Gül A.

JOURNAL OF MOLECULAR STRUCTURE, cilt.1200, 2020 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1200
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1016/j.molstruc.2019.127108
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chimica, Compendex, INSPEC
  • Anahtar Kelimeler: Aza-BODIPY, Photophysics, Singlet oxygen generation, PDT, Bromination, SINGLET OXYGEN GENERATION, HEAVY-ATOM, CRYSTAL-STRUCTURE, FACILE SYNTHESIS, EXCITED-STATE, IN-VITRO, DYES, PHOTOSENSITIZERS, AZADIPYRROMETHENE, PHTHALOCYANINE
  • Yıldız Teknik Üniversitesi Adresli: Evet

Özet

In this study, the effects of incorporation of halogen atoms at different positions and dimerization on the photophysical properties of the aza-BODIPYs were investigated. Aza-BODIPY derivative carrying chlorine atoms on the para-position of the distal phenyl groups (4) and its core-brominated analogue (5) were prepared to establish the external and internal heavy atom effects. Dimerization of aza-BODIPY 4 through oxidative homocoupling with FeCl3 yielded the target homonuclear aza-BODIPY dimer (6). All of the aza-BODIPY derivatives prepared in this study were fully characterized by using UV-Vis, Fluorescence, NMR (H-1, C-13, B-11 and F-19), Mass and X-Ray spectroscopy techniques. The photophysical properties were fully characterized and compared to those of the tetra-phenyl aza-BODIPY derivative (A). Singlet oxygen generation experiments were also performed. The aza-BODIPY derivative possessing bromine atoms at the central core displayed the utmost efficiency for singlet oxygen generation. (C) 2019 Elsevier B.V. All rights reserved.