Synthesis and characterization of trimeric phosphazene based ionic liquids with tetrafluoroborate anions and their thermal investigations.


Journal

Scientific reports
ISSN: 2045-2322
Titre abrégé: Sci Rep
Pays: England
ID NLM: 101563288

Informations de publication

Date de publication:
16 Jul 2020
Historique:
received: 08 05 2020
accepted: 29 06 2020
entrez: 18 7 2020
pubmed: 18 7 2020
medline: 18 7 2020
Statut: epublish

Résumé

The quaternized compounds (PzIL1-9) reacted with sodium tetrafluoroborate (NaBF

Identifiants

pubmed: 32678198
doi: 10.1038/s41598-020-68709-5
pii: 10.1038/s41598-020-68709-5
pmc: PMC7367273
doi:

Types de publication

Journal Article Retracted Publication

Langues

eng

Sous-ensembles de citation

IM

Pagination

11705

Commentaires et corrections

Type : RetractionIn

Références

Akbaş, H. et al. Phosphorus-nitrogen compounds part 27: syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of new phosphazenes bearing secondary amino and pendant (4-fluorobenzyl)spiro groups. Eur. J. Med. Chem.70, 294–307 (2013).
doi: 10.1016/j.ejmech.2013.09.046
Beşli, S., Mutlu Balci, C., Doǧan, S. & Allen, C. W. Regiochemical control in the substitution reactions of cyclotriphosphazene derivatives with secondary amines. Inorg. Chem.57, 12066–12077 (2018).
doi: 10.1021/acs.inorgchem.8b01620
Tümer, Y., Asmafiliz, N., Arslan, G., Kılıç, Z. & Hökelek, T. Phosphorus-nitrogen compounds: Part 45: Vanillinato-substituted cis- and trans-bisferrocenyldispirocyclotriphosphazenes: syntheses, spectroscopic and crystallographic characterizations. J. Mol. Struct.1181, 235–243 (2019).
doi: 10.1016/j.molstruc.2018.12.090
Karadağ, A. & Akbaş, H. Phosphazene-based ionic liquids. Recent Advances in Ionic Liquids (InTech, 2018). https://doi.org/10.5772/intechopen.76613
Akbaş, H. et al. Phosphorus–nitrogen compounds Part 32: structural and thermal characterizations, antimicrobial and cytotoxic activities, and in vitro DNA binding of the phosphazenium salts. J. Therm. Anal. Calorim.123, 1627–1641 (2016).
doi: 10.1007/s10973-015-5001-6
Elmas, G. et al. The syntheses and structural characterizations, antimicrobial activity and in vıtro DNA binding of 4-fluorobenzylspiro(N/O)cyclotrıphosphazenes and their phosphazenium salts. J. Turkish Chem. Soc. Sect. A Chem.3, 25–46 (2016).
Moeller, T. & Kokalis, S. G. The Lewis-base behaviour of some hexa-n-alkylamino triphosphonitriles. J. Inorg. Nucl. Chem.25, 875–881 (1963).
doi: 10.1016/0022-1902(63)80375-9
Zhang, Y., Tham, F. S. & Reed, C. A. Phosphazene cations. Inorg. Chem.45, 10446–10448 (2006).
doi: 10.1021/ic062077f
Mani, N.V. & Wagner, A.J. The crystal structure of compounds with (N–P)
Alberti, M., Mareček, A., Žák, Z. & Pastera, P. Reaction of [P
doi: 10.1002/zaac.19956211027
Tun, Z. M. et al. Group 13 Lewis acid adducts of [PCl
doi: 10.1021/ic201075z
Tun, Z. M. et al. Group 13 superacid adducts of [PCl
doi: 10.1021/acs.inorgchem.5b02341
Elmas, G., Okumuş, A., Kılıç, Z., Çelik, S.P. & Açık, L. The spectroscopic and thermal properties, antimicrobial activities and DNA interactions of 4-(Fluorobenzyl)Spiro(N/O) cyclotriphosphazenium salts. J. Turkish Chem. Soc. Sect. A Chem.4, 993–1016 (2017).
Okumuş, A. et al. Antiproliferative effects against A549, Hep3B and FL cell lines of cyclotriphosphazene-based novel protic molten salts: spectroscopic, crystallographic and thermal results. Chem. Select2, 4988–4999 (2017).
Akbaş, H., Karadağ, A., Aydın, A., Destegül, A. & Kılıç, Z. Synthesis, structural and thermal properties of the hexapyrrolidinocyclotriphosphazenes-based protic molten salts: Antiproliferative effects against HT29, HeLa, and C6 cancer cell lines. J. Mol. Liq.230, 482–495 (2017).
doi: 10.1016/j.molliq.2017.01.067
Allcock, H. R., Levin, M. L. & Austin, P. E. Quaternized cyclic and high polymeric phosphazenes and their ınteractions with tetracyanoquinodimethane. Inorg. Chem.25, 2281–2288 (1986).
doi: 10.1021/ic00234a002
Omotowa, B. A., Phillips, B. S., Zabinski, J. S. & Shreeve, J. M. Phosphazene-based ionic liquids: synthesis, temperature-dependent viscosity, and effect as additives in water lubrication of silicon nitride ceramics. Inorg. Chem.43, 5466–5471 (2004).
doi: 10.1021/ic049483o
Veldboer, K., Karatas, Y., Vielhaber, T., Karst, U. & Wiemhöfer, H.-D. Cyclic phosphazenes for the surface modification of lanthanide phosphate-based nanoparticles. Zeitschrift für Anorg. und Allg. Chemie634, 2175–2180 (2008).
doi: 10.1002/zaac.200800297
US9206210B2. Ionic liquids, electrolyte solutions including the ionic liquids, and energy storage devices including the ionic liquids: Google Patents. Available at: https://patents.google.com/patent/US9206210B2/en . Accessed 6 Dec 2019.
Akbaş, H. et al. Synthesis, and spectroscopic, thermal and dielectric properties of phosphazene based ionic liquids: OFET application and tribological behavior. New J. Chem.43, 2098–2110 (2019).
doi: 10.1039/C8NJ04948C
Destegül, A. et al. Synthesis and structural and thermal properties of cyclotriphosphazene-based ionic liquids: tribological behavior and OFET application. Ionics (Kiel).25, 3211–3222 (2019).
doi: 10.1007/s11581-019-02846-4
Rapko, J. N. & Feistel, G. The reactions of trimethyloxonium fluoroborate with alkylamino- and phenyl-substituted cyclotriphosphonitrlles. Inorg. Chem.9, 1401–1405 (1970).
doi: 10.1021/ic50088a022
US7718826B2. Ionic compound: Google Patents. https://patents.google.com/patent/US7718826B2/en?oq=M.+Otsuki%2C+H.+Kanno%2C+Ionic+compound.+US+Patent+7%2C718%2C826+ . Accessed 3 May 2020.
US7951495B2. Non-aqueous electrolyte for battery and non-aqueous electrolyte battery comprising the same as well as electrolyte for electric double layer capacitor and electric double layer capacitor comprising the same: Google Patents. Available at: https://patents.google.com/patent/US7951495B2/en . Accessed 6 Dec 2019.
Singh, R. K. et al. Phosphazene-based novel organo-inorganic hybrid salt: synthesis, characterization and performance evaluation as multifunctional additive in polyol. RSC Adv.7, 13390–13397 (2017).
doi: 10.1039/C6RA26186H
Çiftçi, G. Y., Şenkuytu, E., Bulut, M. & Durmuş, M. Novel coumarin substituted water soluble cyclophosphazenes as ‘turn-off’ type fluorescence chemosensors for detection of Fe
doi: 10.1007/s10895-015-1672-4
Fujimoto, T. & Awaga, K. Electric-double-layer field-effect transistors with ionic liquids. Phys. Chem. Chem. Phys.15, 8983–9006 (2013).
doi: 10.1039/c3cp50755f
Tang, W. et al. Recent progress in printable organic field effect transistors. J. Mater. Chem. C7, 790–808 (2019).
doi: 10.1039/C8TC05485A
Gebbie, M. A. et al. Long range electrostatic forces in ionic liquids. Chem. Commun.53, 1214–1224 (2017).
doi: 10.1039/C6CC08820A
Chen, C. et al. Synthesis of new polyelectrolytes via backbone quaternization of poly(aryloxy- and alkoxyphosphazenes) and their small molecule counterparts. Macromol.45, 1182–1189 (2012).
doi: 10.1021/ma202619j
Carriedo, G. A., Alonso, F. J. G., González, P. A. & Menéndez, J. R. Infrared and Raman spectra of the phosphazene high polymer [NP(O
doi: 10.1002/(SICI)1097-4555(199804)29:4<327::AID-JRS245>3.0.CO;2-5

Auteurs

Ahmet Karadağ (A)

Department of Chemistry, Faculty of Arts and Sciences, Yozgat Bozok University, 66200, Yozgat, Turkey. ahmet.karadag@bozok.edu.tr.

Hüseyin Akbaş (H)

Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpaşa University, Tokat, Turkey.

Ali Destegül (A)

Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpaşa University, Tokat, Turkey.

Çiğdem Çakırlar (Ç)

Department of Physics, Gebze Technical University, Kocaeli, Turkey.

Yusuf Yerli (Y)

Department of Physics, Yıldız Technical University, Istanbul, Turkey.

Zeynel Kılıç (Z)

Department of Chemistry, Ankara University, Ankara, Turkey.

Fatih Sen (F)

Department of Biochemistry, University of Dumlupınar, Kütahya, Turkey. fatih.sen@dpu.edu.tr.

Classifications MeSH