Synthesis of N,N-spiro-bridged bis(cyclotriphosphazene) derivatives bearing aryl thio groups and their comparison with alkoxy and amino derivatives

Mutlu Balcı, Ceylan; Palabıyık, Duygu; Beşli, Serap

doi:10.1016/j.ica.2024.121953

Inorganica Chimica Acta

2024

DOI: 10.1016/j.ica.2024.121953

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Synthesis of N,N-spiro-bridged bis(cyclotriphosphazene) derivatives bearing aryl thio groups and their comparison with alkoxy and amino derivatives

Ceylan Mutlu Balcı,

Duygu Palabıyık,

Serap Beşli

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Phosphorus–Nitrogen Compounds: Part 76. Design and Syntheses of Dispiro- and Trispiro(N/N)cyclotriphosphazenes: Conformational and Structural Analyses, Chirality, Electrochemical, Dye-Sensitized Solar Cells, and Bioactivity Studies

Cemaloğlu,

Asmafiliz,

Tümer

et al. 2024

Inorg. Chem.

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The reactions of monospirocyclotriphosphazenes (1 and 2) with N-methyl-1,3-diaminopropane gave unsymmetrical cis-(3 and 5) and trans-(4 and 6) dispirocyclotriphosphazenes. Trans−cis−trans (tct) (7 and 11), cis−cis−cis (ccc) (8 and 12), trans−trans−cis (ttc) (9 and 13), and cis−trans−trans (ctt) (14) trispirocyclotriphosphazenes were obtained from the reactions of 3 and 5 and 4 and 6 with N-methyl-1,3-diaminopropane. cis-Dispirocyclotriphosphazenes (3 and 5) exist as "pseudomesoracemates", while trans-dispirocyclotriphosphazenes (4 and 6) are in "racemates". The existences of cis-3 and trans-4 as "pseudomesoracemate" and "racemate" were confirmed by 31 P NMR spectra recorded by the addition of "chiral solvating agent (CSA)". X-ray crystallography proved that the absolute configurations of each enantiomer of cis-5 and trans-6 are SS′ and RS′. Trispirocyclotriphosphazenes tct, ttc, ccc, and ctt exist as racemates, pseudomesoracemate, and meso forms. Furthermore, Hirshfeld surface analysis of the crystal structures of cis-5 and trans-6 revealed that the most significant contribution to crystal packing comes from H•••H (58.2 and 57.6%, respectively). An oxidation−reduction wave was detected in the reversible cyclic voltammograms of the phosphazenes. The highest power conversion efficiency in dye-sensitized solar cell studies was obtained with cis-5. Additionally, trans-6 exhibited the lowest minimal inhibitory concentration value (78.1 μM) against Candida tropicalis, and it was observed to cleave pBR322 plasmid DNA.

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Phosphorus–Nitrogen Compounds: Part 76. Design and Syntheses of Dispiro- and Trispiro(N/N)cyclotriphosphazenes: Conformational and Structural Analyses, Chirality, Electrochemical, Dye-Sensitized Solar Cells, and Bioactivity Studies

Cemaloğlu,

Asmafiliz,

Tümer

et al. 2024

Inorg. Chem.

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Synthesis of N,N-spiro-bridged bis(cyclotriphosphazene) derivatives bearing aryl thio groups and their comparison with alkoxy and amino derivatives

Cited by 1 publication

References 41 publications

Phosphorus–Nitrogen Compounds: Part 76. Design and Syntheses of Dispiro- and Trispiro(N/N)cyclotriphosphazenes: Conformational and Structural Analyses, Chirality, Electrochemical, Dye-Sensitized Solar Cells, and Bioactivity Studies

Phosphorus–Nitrogen Compounds: Part 76. Design and Syntheses of Dispiro- and Trispiro(N/N)cyclotriphosphazenes: Conformational and Structural Analyses, Chirality, Electrochemical, Dye-Sensitized Solar Cells, and Bioactivity Studies

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