Synthesis and properties of highly lipophilic phosphazene bases. Issue 22 (31st May 2017)

• Record Type: Journal Article
• Authors: Selberg, Sigrid; Rodima, Toomas; Lõkov, Märt; Tshepelevitsh, Sofja; Haljasorg, Tõiv; Chhabra, Sahil; Kadam, Sandip A.; Toom, Lauri; Vahur, Signe; Leito, Ivo
• Is Part Of: Tetrahedron letters. Volume 58:Issue 22(2017)
• Page Start: 2098
• Page End: 2102
• Publication Date: 2017-05-31
• Subjects: Phenylphosphazenes -- Lipophilicity -- LogP -- pKa -- Staudinger reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.04.039
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Synthesis of twelve novel phosphazene-based compounds. Unusual combination of properties: basicity, high lipophilicity, significant spectral differences in the visible region. Modified log P and p K a measurement protocol for highly lipophilic compounds. Abstract: Twelve novel phosphazene bases (X-C6 H4 -NN-C6 H4 -NPR3 ) with an unusual combination of properties – high lipophilicity of both neutral and charged forms, lack of localized charges in the cations, and strong spectral changes upon protonation/deprotonation – were synthesized using the Staudinger reaction and characterized by UV–Vis spectra, p K a values and lipophilicities (log P values). The bases could potentially be useful as working agents in optical sensors and acid-base indicators for lipophilic membranes.