Synthesis and singlet oxygen generation of pyrazinoporphyrazines containing dendrimeric aryl substituents

Pyrazinoporphyrazines and tribenzopyrazinoporphyrazines were synthesized and studied towards their potential applications in photodynamic therapy. The macrocycles were obtained via Linstead macrocyclization with good yields. The expansion of the porphyrazine periphery with hyperbranched aryl substit...

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Published inNew journal of chemistry Vol. 41; no. 9; pp. 3586 - 3594
Main Authors Tillo, Adam, Mlynarczyk, Dariusz T., Popenda, Lukasz, Wicher, Barbara, Kryjewski, Michal, Szczolko, Wojciech, Jurga, Stefan, Mielcarek, Jadwiga, Gdaniec, Maria, Goslinski, Tomasz, Tykarska, Ewa
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2017
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
DYES
PHOTODYNAMIC THERAPY
FLUORESCENCE
ANALOGS
PHOTOSENSITIZERS
OPTICAL-PROPERTIES
PHOTOPHYSICAL PROPERTIES
PHTHALOCYANINES
DERIVATIVES
TETRAPYRAZINOPORPHYRAZINES
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Summary:Pyrazinoporphyrazines and tribenzopyrazinoporphyrazines were synthesized and studied towards their potential applications in photodynamic therapy. The macrocycles were obtained via Linstead macrocyclization with good yields. The expansion of the porphyrazine periphery with hyperbranched aryl substituents was beneficial in terms of purification and isolation of compounds, effectively hampering their aggregation tendency in different concentrations. The obtained macrocycles were assessed for their singlet oxygen generation quantum yields and revealed far better efficacies for tribenzopyrazinoporphyrazines than pyrazinoporphyrazines. A comparison of the crystal packing of two 2,3-dicyanopyrazine derivatives revealed that the recurring motif of the supramolecular architecture is a dimer formed by pi-pi stacking interactions between aromatic pyrazine and phenyl rings of the inversion center related molecules.
ISSN:1144-0546
1369-9261
DOI:10.1039/c6nj03886g