Synthesis and structural and thermal properties of cyclotriphosphazene-based ionic liquids: tribological behavior and OFET application

Destegül, Ali; Akbaş, Hüseyin; Karadağ, Ahmet; Canımkurbey, Betül; Yerli, Yusuf; Tekin, Kadir Cihan; Malayoğlu, U.; Kılıç, Zeynel

doi:10.1007/s11581-019-02846-4

Cited by 11 publications

(11 citation statements)

References 45 publications

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“…The characteristic frequencies of the Ar-H bonds were observed between 3,072 and 3,033 cm −1 . The νC-F stretching bands in the PzILs (PzIL1a-9a) are in agreement with the literature values of the mono fluorinated benzenes 20,21 . Besides, the νPOC absorption bands of PzILs (PzIL1a-9a) were found to be in the range of 973-945 cm −1 .…”

Section: Resultssupporting

confidence: 90%

“…On the other hand, the 1 H NMR data of the PzILs (PzIL1a-9a) were reported in the "Experiment" section, and the expected J coupling constants and δ shift values of hydrogen atoms were elucidated. The 3 J HH , 3 J FH, and 4 J FH and δ shifts of H 2 /H 6 and H 3 /H 5 protons of the FPh groups of the PzILs (PzIL1a-9a) were interpreted, and these values were found to be following the literature findings 1,20,21,27 . The average 3 J HH , 3 J FH, and 4 J FH values of H 2 /H 6 and H 3 /H 5 protons of the FPh groups were 3 J HH = 8.1 Hz, 3 J FH = 8.8 Hz, and 4 J FH = 5.7 Hz, respectively.…”

Section: Resultssupporting

confidence: 61%

“…This is followed by PzILs containing the I − anions and the BF 4 − anions, respectively. For example, the decomposition temperature of the PzIL4a (109 °C) is lower than that of PzILs containing NTf 2 − anions (292 °C) and I − anions (236 °C) as compared to ILs having the same cationic part in the literature 20,21 .…”

Section: Resultsmentioning

confidence: 89%

“…However, as PzILs (PzIL1a-9a) obtained were dissolved in water, the solution mixture was evaporated to dryness and extracted with acetone. PzILs that appeared highly hygroscopic were dried under dynamic vacuum for several days 17,20,21 . However, it was impossible to keep them in a dehydrated state after exposure to the laboratory and during their transport for chemical analysis.…”

Section: Resultsmentioning

confidence: 99%

“…We have followed this behavior by FTIR spectroscopy, elemental analysis, and thermal analysis techniques. [16][17][18]20,21,30 . However, in the presence of the NTf 2 − and trifluoromethylsulfonate (OTf − ) anions, PzIL s are insoluble in water and are obtained as liquids 17,20,21,30 .…”

Section: Resultsmentioning

confidence: 99%

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RETRACTED ARTICLE: Synthesis and characterization of trimeric phosphazene based ionic liquids with tetrafluoroborate anions and their thermal investigations

Karadağ

Akbaş

Destegül

et al. 2020

Sci Rep

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The quaternized compounds (PzIL1-9) reacted with sodium tetrafluoroborate (NaBF 4) to generate phosphazene based ionic liquids (PzILs), PzIL1a-9a. The newly synthesized ionic compounds (PzIL1a-9a) were verified using elemental CHN analyses and functional and spectroscopic (FTIR and 1 H, 13 c, 31 P-NMR) analyses techniques. The thermal properties of PzIL1a-9a were investigated using thermogravimetric analysis (TGA). According to the initial decomposition temperature values calculated based on the TGA thermograms, PzIL7a (213 °C) was recognized to be more thermally stable than the other PzILs studied. PzIL1a-9a exhibited good solubility in the water and demonstrate a typical dielectric relaxation behavior, conductivity levels for both low and high-frequency regions. AC conductivity mechanisms and dielectric relaxation behavior of each sample are investigated by fabricating parallel plate capacitors. The nucleophilic substitution reactions of phosphazenes are well known 1-3. Thus, a broad array of poly and cyclophosphazene derivatives were obtained. Nevertheless, PzILs obtained by the quaternization of the skeletal or the side-group nitrogen atoms of phosphazene have received much less attention 4. Compounds formed by the protonation of the ring nitrogen atom of the cyclophosphazenes are defined as protic molten salts (PMOSs) or protic ionic liquids (PILs) 5,6. Protonation of the ring nitrogen with various acids was carried out, and the protonation was first determined by infrared and NMR methods 7,8. In later years, the crystal structures of N 3 P 3 Cl 2 (NHPr i) 4 •HCI and [N 3 P 3 HCl 4 (NH 2) 2 ] + [N(POCl 2) 2 ] − were determined by X-ray analysis 9,10. Tun and colleagues observed two types of products, reacting with N 3 P 3 Cl 6 and group 13 Lewis acids.[PCl 2 N] 3 •MX 3 obtained by excluding water or HX is the main product. Whenever MX 3 (AlCl 3 , GaCl 3 , AlBr 3) was used, water traces were always found, and by isolating [PCl 2 N] 3 •HMX 4 (HMX 4 : HAlCl 4 , HGaCl 4 , HAlBr 4) structures as the second product, they detected the location of the protonation by X-ray crystallography 11,12. In recent years, PILs have been synthesized using a variety of cyclophosphazene compounds and bulky acids (salicylic, gentisic, γ-resorcylic acids), and the biological activity of these PMOSs has been investigated 13-15. In addition to these, phosphazenes containing aliphatic and aromatic substituents having terminal tertiary amino groups were synthesized and then quaternized with methyl iodide 16-21. The PzILs with different anions (chloride, Cl − , bis-trifluoromethane sulfonimide, NTf 2 − and tetrafluoroborate, BF 4 −) were obtained by simple anion exchange reactions 17,20-25. On the other hand, PzILs with various molecular weights or different average chain lengths have been used as antibacterial, antifungal and anticancer agents 5,6,13-15 , lubricants 17,25 , adsorbents and surface modifiers 18 , a gate dielectric layer for OFETs 20,21 , electrolyte solutions 19,23,24 and chemosensors for metal ions 26 .

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Section: Resultssupporting

confidence: 90%

Section: Resultssupporting

confidence: 61%

Section: Resultsmentioning

confidence: 89%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 3 more Smart Citations

RETRACTED ARTICLE: Synthesis and characterization of trimeric phosphazene based ionic liquids with tetrafluoroborate anions and their thermal investigations

Karadağ

Akbaş

Destegül

et al. 2020

Sci Rep

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Charge carrier performance of phosphazene-based ionic liquids doped hole transport layer in organic light-emitting diodes

et al. 2020

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Novel alkyne chromophore of the isophorone derivatives: synthesis, electrochemical evaluation, DFT, and processable bottom contact/top-gate OFET applications

Canimkurbey,

Kir,

Eryilmaz

et al. 2024

J Mater Sci: Mater Electron

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Fused alkyne molecules are important in organic semiconductors due to their desirable properties. Here, we report the design and synthesis of a new series of A–π–D molecules (III–VII) that can serve as mild electron acceptors to generate wide-bandgap p-type small compounds for use in organic field-effect transistors. The incorporation of donor units into fused isophorone frameworks can be used to tune the frontier molecular orbital energies. The electrochemical, optical, and thermal properties of the compounds were characterized. Compound VI, which has a fused phenyl-substituted alkyne moiety, had the highest occupied molecular orbital energy level as determined by optical and electrochemical analysis. Density functional theory calculations revealed that compounds VI and III had lower hole reorganization energy (λh) than the corresponding isophorone extended conjugated-based compounds (I–II). Conversely, compounds I and II had lower electron reorganization energy (λe) than the corresponding fused alkyne compounds. This is in line with the observed adiabatic ionization potential and electron affinity values. Consequently, devices fabricated with compound VI exhibited high mobility and low threshold voltage.

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Synthesis and structural and thermal properties of cyclotriphosphazene-based ionic liquids: tribological behavior and OFET application

Cited by 11 publications

References 45 publications

RETRACTED ARTICLE: Synthesis and characterization of trimeric phosphazene based ionic liquids with tetrafluoroborate anions and their thermal investigations

RETRACTED ARTICLE: Synthesis and characterization of trimeric phosphazene based ionic liquids with tetrafluoroborate anions and their thermal investigations

Charge carrier performance of phosphazene-based ionic liquids doped hole transport layer in organic light-emitting diodes

Novel alkyne chromophore of the isophorone derivatives: synthesis, electrochemical evaluation, DFT, and processable bottom contact/top-gate OFET applications

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