Phosphorus-nitrogen compounds: part 71. Novel unsymmetrically-substituted dispiro-cyclotriphosphazenes: synthesis, characterization, antituberculosis activity, and phototunable charge storage studies

Basit Öğe Kaydı
dc.contributor.authorCemaloglu, Resit
dc.contributor.authorBerberoglu, Ipek
dc.contributor.authorYakut, Mehtap
dc.contributor.authorBinici, Arzu
dc.contributor.authorAsmafiliz, Nuran
dc.contributor.authorKilic, Zeynel
dc.contributor.authorGuzel, Remziye
dc.date.accessioned2024-04-24T16:24:05Z
dc.date.available2024-04-24T16:24:05Z
dc.date.issued2023
dc.departmentDicle Üniversitesien_US
dc.description.abstractThe aim of this research is to synthesize and characterize new organic-inorganic hybrid multi-heterocyclic dichlorodispiro(N/N)cyclotriphosphazenes and to elucidate their antituberculosis activities. To achieve this aim, primarily, trans (6a-11a) and cis (6b-11b) unsymmetrical dichlorodispiro(N/N)cyclotriphosphazenes were obtained from ferrocenyldiamines (4 and 5) and benzyl-pendant armed tetrachloromonospirophosphazenes as starting materials. Several spectroscopic techniques (mass spectrometry, FTIR, and 1H, 13C, and 31P NMR), as well as elemental analysis, were employed to characterize the new phosphazenes. All unsymmetrically substituted phosphazenes are expected to be racemic mixtures (RR '/SS ' and RS '/SR ') due to two different stereogenic P-centers. In addition, the molecular and crystal structures of cis-6b, cis-10b, and cis-11b isomers were elucidated via single-crystal X-ray crystallography. They belong to centrosymmetric C2/c, P21/c, and P1 space groups, respectively; thus, their crystal lattices must contain both the enantiomers, RR '/SS ' or SR '/RS '. Moreover, only one oxidation-reduction wave was observed for the ferrocenyl-dispirophosphazenes in the reversible cyclic voltammograms. The HOMO and LUMO energy values of the phosphazenes were calculated using the oxidation potential (Eox) and the optical band gap values using Tauc plots, respectively. To determine the phototunable charge storage properties of the four dispirophosphazenes, their memory functions were investigated under UV illumination. The antituberculosis activities of the dichlorodispiro(N/N)cyclotriphosphazenes trans-6a, cis-6b, trans-10a, and cis-10b against Mycobacterium tuberculosis H37Rv (ATCC 27294) strain were evaluated. The results showed that among these compounds, trans-6a (MIC value 18 mu g mL-1) was much more effective than the other phosphazenes. Unsymmetrical cis/trans dispirocyclotriphosphazenes were prepared. The electrochemical behaviors and phototunable charge storage properties of the compounds were determined. The antituberculosis activities were examined against M. tuberculosis H37Rv.en_US
dc.description.sponsorshipZ. K. thanks the Turkish Academy of Sciences (TBA) for partial support of this work. T. H. is grateful to the Hacettepe University Scientific Research Project Unit (Grant No. 013 D04 602 004).en_US
dc.description.sponsorshipZ. K. thanks the Turkish Academy of Sciences (TUBA) for partial support of this work. T. H. is grateful to the Hacettepe University Scientific Research Project Unit (Grant No. 013 D04 602 004).en_US
dc.identifier.doi10.1039/d3nj04099b
dc.identifier.endpage19800en_US
dc.identifier.issn1144-0546
dc.identifier.issn1369-9261
dc.identifier.issue42en_US
dc.identifier.scopus2-s2.0-85175255114
dc.identifier.scopusqualityQ2
dc.identifier.startpage19788en_US
dc.identifier.urihttps://doi.org/10.1039/d3nj04099b
dc.identifier.urihttps://hdl.handle.net/11468/16479
dc.identifier.volume47en_US
dc.identifier.wosWOS:001084358300001
dc.identifier.wosqualityN/A
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoenen_US
dc.publisherRoyal Soc Chemistryen_US
dc.relation.ispartofNew Journal of Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subject[No Keyword]en_US
dc.titlePhosphorus-nitrogen compounds: part 71. Novel unsymmetrically-substituted dispiro-cyclotriphosphazenes: synthesis, characterization, antituberculosis activity, and phototunable charge storage studiesen_US
dc.titlePhosphorus-nitrogen compounds: part 71. Novel unsymmetrically-substituted dispiro-cyclotriphosphazenes: synthesis, characterization, antituberculosis activity, and phototunable charge storage studies
dc.typeArticleen_US

Dosyalar

Koleksiyon

WoS İndeksli Yayınlar Koleksiyonu
Scopus İndeksli Yayınlar Koleksiyonu