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Relevant academic research and scientific papers

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 porphyraz

Magnesium tetrapyrazinoporphyrazines: Tuning of the pKa of red-fluorescent pH indicators

Magnesium(ii) tetrapyrazinoporphyrazines (TPyzPzs) are excellent red fluorophores (λF ～ 663 nm, ΦF ～ 0.53 in THF). In this work, a series of magnesium(ii) complexes of unsymmetrical TPyzPzs bearing one or two phenol substituents was prepared. Suitable substitutions on the phenolic moiety tuned its pKa in the range of 5.5 to 13. Deprotonation of the phenolic group at higher pH induced a strong donor (phenolate) in the macrocycle that led to pH-dependent quenching of the red fluorescence of these indicators. pH sensing was proved in water solutions after the incorporation of TPyzPzs into two delivery systems-microemulsions and liposomes. The latter also serves as a simple model of biomembranes. Finally, a wavelength-ratiometric probe was constructed by the incorporation of a TPyzPz indicator and lipophilic pH-nonsensitive BODIPY dye into liposomes. Synthetic precursors for TPyzPzs, substituted pyrazine-2,3-dicarbonitriles, also represent donor-acceptor systems and the pH-dependent changes in absorption spectra may be easily visible to the naked eye.

Synthesis and optical/thermal properties of low molecular mass V-shaped materials based on 2,3-dicyanopyrazine

A novel series of luminescent low molecular mass materials containing a 2,3-dicyanopyrazine central core were synthesized through an esterification reaction between diphenol 10 and different aromatic carboxylic acids 1-6, containing terminal long alkyl chains. They have a similar V-shaped geometry with lack of planarity between the two arms, confirmed by the X-ray structure of the central core. The optical and thermal properties of these compounds were evaluated. They show blue fluorescence in solution (λemmax 440-480 nm) with quantum fluorescence yields (ΦF) from 0.003 to 0.1 and Stokes shifts of around 90 nm. In solid state, optical band gaps (Eg) were from 3.14 to 3.32 eV. Thin films of 11, 13, and 14 exhibited blue fluorescence (λemmax 430-456 nm), and 12, 15, and 16 (more bulky) displayed green fluorescence (λemmax 488-512 nm). Most of the materials exhibited good thermal stability, exhibiting an amorphous glassy state after melting. Transparent amorphous films were easily obtained through spin coating and characterized by AFM analysis.