Synthesis, photophysical properties and theoretical evaluation of alkyl-linked porphyrin – BODIPY dyads


Dyes and Pigments, vol.206, 2022 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 206
  • Publication Date: 2022
  • Doi Number: 10.1016/j.dyepig.2022.110573
  • Journal Name: Dyes and Pigments
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aerospace Database, Chemical Abstracts Core, Chimica, Communication Abstracts, Compendex, INSPEC, Metadex, Civil Engineering Abstracts
  • Keywords: Alkyl spacer, BODIPY dyads, DFT, Energy transfer, FRET efficiency, Porphyrin, TD-DFT
  • Ankara Haci Bayram Veli University Affiliated: Yes


© 2022 Elsevier LtdNovel porphyrin-BODIPY Dyads linked by alkyl chains of different lengths as molecular conjugates were prepared and their intramolecular energy transfer properties have been investigated. Steady-state absorption and emission spectra have shown the successful intramolecular energy transfer (FRET) from BODIPY to porphyrin units approved with the calculated Förster radii and FRET efficiencies. Alkyl chain shortening has revealed an explicit increase in energy transfer as it could be expected. Further, DFT and TD-DFT studies for the synthesized dyads were carried out and frontier molecular orbital energies were investigated at the HSEH1PBE/6-31+G** theory level. Strongly electron-withdrawing C6F5- substituents on the porphyrin periphery extended the HOMO-LUMO gap in contrast to the 4-CF3C6H4- substituent from ca. 2.37 eV to ca. 2.50 eV. Open-circuit voltage values (Voc), reorganization energies (λe and λh), ionization potentials, and adiabatic electron affinities were calculated to evaluate the optical and electronic behaviors of Dyads. Calculated Voc values exceeding 1.00 V, and low reorganization energies of the Dyads indicate that they are promising structures for developing new photovoltaics.