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Tetra[6,7]quinoxalinoporphyrazines: The Effect of an Additional Benzene Ring on Photophysical and Photochemical Properties
Author(s) -
Novakova Veronika,
Zimcik Petr,
Miletin Miroslav,
Kopecky Kamil,
Musil Zbynek
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901149
Subject(s) - chemistry , pyrazine , heteroatom , porphyrazine , benzene , photochemistry , singlet oxygen , pyridine , tetra , ring (chemistry) , singlet state , porphyrin , absorption (acoustics) , medicinal chemistry , stereochemistry , oxygen , organic chemistry , excited state , physics , nuclear physics , acoustics
Synthetic methods for a series of zinc tetra[6,7]quinoxalinoporphyrazines (6,7‐TQP) with peripheral chains connected through the S, O and N heteroatoms as well as through the C–C bond were developed. Photophysical and photochemical properties of 6,7‐TQP were compared with tetrapyrazinoporphyrazines (TPP) bearing the same peripheral substituents to disclose the effect of insertion of a benzene ring between the pyrazine and porphyrazine moieties. The influence of the peripheral heteroatom in the group of 6,7‐TQP is also discussed. Prepared 6,7‐TQP have their main absorption band (Q‐band) strongly batho‐ and hyperchromically shifted ( λ max = 730–770 nm in pyridine, ϵ up to 5 dm 3 mol –1 cm –1 ) in comparison to TPP. They showed high singlet oxygen quantum yields ( Φ Δ = 0.50–0.74) and relatively lowfluorescence quantum yields ( Φ F < 0.08).