Synthesis, and spectroscopic, thermal and dielectric properties of phosphazene based ionic liquids: OFET application and tribological behavior

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

doi:10.1039/c8nj04948c

Cited by 22 publications

(22 citation statements)

References 52 publications

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“…PzILs are prepared by quaternization of a wide variety of phosphazenes either at the sidegroup or at the skeletal nitrogen atoms. These ILs have been used as anticancer, antibacterial reagents [31][32][33][34], adsorbents and surface modifiers of fluorescent nanoparticles [35], lubricants [36,37], chemosensors for metal ions [38], electrolyte solutions for energy storage devices [39][40][41], as gate dielectric layer for OFETs [42], or as polyelectrolytes [26,43,44].…”

Section: Applications Of Phosphazene-based Ionic Liquidsmentioning

confidence: 99%

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Phosphazene-Based Ionic Liquids

Karadağ¹,

Akbaş²

2018

Recent Advances in Ionic Liquids

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This chapter presents the definition, synthesis, and possible application of cyclo and polyphosphazene-based ionic liquids (PzILs). PZILs constitute an alternative class of phosphorus nitrogen compounds and their derivatives have been widely used in biologically-active materials, electrolytes, lubricants, catalysts or nanomaterials. Considerable information is available on substitution reactions taking place at the phosphorus atoms of poly and cyclophosphazenes, thus, a wide variety of phosphazene derivatives have been obtained. However, quaternization of ring nitrogen atoms has received less attention. In addition, phosphazenes containing aliphatic and aromatic substituents with terminal tertiary amino groups are synthesized and subsequently quaternized with methyl iodide. The successive metathesis with salts such as LiN(SO 2 CF 3) 2 or NaBF 4 gives the respective PzILs. In the compounds identified as protonic ionic liquids (PILs) or protic molten salts (PMOSs), the positively charged position is determined by X-ray diffraction study. PzILs are also soluble in water and in many polar organic solvents.

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Section: Applications Of Phosphazene-based Ionic Liquidsmentioning

confidence: 99%

“…On/ off ratios of these OFETs are about 10 2 . The low value of on-off ratio could be caused by the increasing thickness and doping level of active organic layer [42].…”

Section: A Gate Dielectric Layer For Ofetsmentioning

confidence: 99%

Phosphazene-Based Ionic Liquids

Karadağ¹,

Akbaş²

2018

Recent Advances in Ionic Liquids

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“…Herein, we reported the first examples of BODIPY-bridged cyclotriphosphazene dimers (4P-6P). Unsubstituted, iodinated, and brominated distyryl-BODIPY derivatives (4)(5)(6) bearing alkoxy functional groups were reacted with trimer and mono-BODIPY-bridged cyclotriphosphazene (4P-6P) derivatives were synthesized (Scheme). All of the prepared compounds were characterized by mass, 31 P, 1 H, and 13 C NMR spectroscopy.…”

Section: Introductionmentioning

confidence: 99%

Novel BODIPY-bridged cyclotriphosphazenes

2020

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Three new 2-component unsubstituted (4P), diiodo-(5P), and dibromo-(6P) distyryl-BODIPY-bridged cyclotriphosphazene dimers were designed and synthesized. The newly synthesized BODIPY-cyclotriphosphazene systems were characterized by 1 H, 13 C, and 31 P NMR spectroscopy. The photophysical properties of the distryl-BODIPYs (4-6) and BODIPY-cyclotriphosphazene dyads (4P-6P) were studied by UV-Vis absorption and fluorescence emission spectroscopy. In these derivatives, the bino-type cyclotriphosphazene derivative bearing unsubstituted BODIPY unit 4 P exhibited high fluorescence and no singlet oxygen generation due to the lack of spin converter. The attachment of heavy atoms (iodine and bromine) enabled the production of singlet oxygen. The bino-type BODIPY-cyclotriphosphazenes (5P and 6P) were also used as triplet photosensitizers in the photooxidation of 1,3-diphenylisobenzofuran to endoperoxide via generation of the singlet oxygen in dichloromethane. The singlet oxygen production of these compounds was also investigated via a direct method and produced a singlet oxygen phosphorescence peak at 1270 nm.

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“…Organophosphorus compounds are increasingly used in modern organic chemistry because of their potential in such varied domains as biology (Akbaş et al, 2013;Mudryk et al, 2015), medicine (Cupistiet al, 2013;Dabrzalska et al, 2015), agriculture (as plant growth regulators) and biochemistry (Engel et al, 2003). They are also of great interest as precursors in organic synthesis (Kann et al, 2003;Bricklebank et al, 2003).…”

Section: Introductionmentioning

confidence: 99%

“…Bibliographic research shows that the reaction of the trivalent phosphorus derivatives with certain polyhalogenoalkanes leads to the formation of a number of products (Waschbüsch et al, 1996;Nai et al, 1997)some of which have numerous applications in industry and biology (Halazy et al,1996).The reactivity of trivalent phosphorus with regard to polyhalogenomethanes has already been the subject of several studies (Barhoumi et al, 2018;Bakkas et al, 2000). This reactivity varies according to the nature of the substituents carried by the phosphorus atom and increases as its electropositivity increases.…”

Section: Introductionmentioning

confidence: 99%

Theoretical Study of the Regioselectivity of the Reaction Between Diethyl(Trichloromethy1)Phosphonateand Triethylphosphite Using the DFT Method

2019

European Reviews of Chemical Research

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In this study we used the DFT/B3LYP/6-311G(d,p) quantum mechanical method to propose a theoretical explanation of the regioselectivity observed experimentally in the reaction between diethyl(trichloromethy1)phosphonate and triethylphosphite using a variety of approaches, notably frontier molecular orbital theory and calculation of activity energies and reactivity indices. Our results show that triethylphosphite functions as a nucleophile while diethyl(trichloromethy1) phosphonate behaves as an electrophile. The nucleophilic attack takes place preferentially at the chlorine atom of diethyl (trichloromethy1)phosphonate rather than at the carbon, and the reaction is polar and regioselective.

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Synthesis, and spectroscopic, thermal and dielectric properties of phosphazene based ionic liquids: OFET application and tribological behavior

Abstract: Mono(4-fluorobenzyl)cyclotriphosphazene derivatives with (dimethylamino)ethoxy (Pz1a–2a) and (dimethylamino)propoxy (Pz1b–2b) chains and their ionic liquids (PzIL1–PzIL4 and PzIL1a–PzIL4a) were synthesized.

Cited by 22 publications

References 52 publications

Phosphazene-Based Ionic Liquids

Phosphazene-Based Ionic Liquids

Novel BODIPY-bridged cyclotriphosphazenes

Theoretical Study of the Regioselectivity of the Reaction Between Diethyl(Trichloromethy1)Phosphonateand Triethylphosphite Using the DFT Method

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