Dielectric and Thermal Properties of 2,2-(3-(Substitüted-fluorophenyl)- 1-(4-oxyphenyl)prop-2-en-1-one)-4,4,6,6-bis[spiro(2',2"-dioxy-1',1"-biphenylyl]Cyclotriphosphazenes

In this study, it is aimed to determine the dielectric and thermal properties of side group substituted fluorine cyclotriphosphazene compounds. In this purpose, 4'-hydroxy-substituted chalcone compounds (1a-c) were initially synthesized by reacting 4'-hydroxyacetophenone with 2-fluorobenzaldehyde (a), 3- fluorobenzaldehyde (b) and 4-fluorobenzaldehyde (c) in ethanol solution in the presence of NaOH. Afterwards, 2,2-dichloro-4,4,6,6-[spiro(2',2''-dioxy-1',1''-biphenylyl)]cyclotriphosphazene (DPP) was obtained by reacting 2,2'-dioxybiphenol with hexachlorocyclotriphosphazene (HCP). The DPP compound was then reacted with the synthesized 1a-c compounds to obtain chalcone-substituted cyclotriphosphazene compounds (BPCP 1-3). The structures of the substituted cyclotriphosphazene compounds were characterized by FT-IR, 1H, 13C-APT and 31P-NMR spectroscopy methods, and the thermal behavior of the compounds was determined by DSC and TGA thermal analysis methods. The TGA results show that the compounds have a stable structure even at high temperatures. The dielectric constant, dielectric loss factor and AC conductivity values of phosphazene compounds (BPCP 1-3) were determined with an impedance analyzer (between 100 Hz and 30 kHz) as a function of frequency versus increasing temperature. In addition, the capacitance and dielectric constant values of the compounds decreased in increasing frequency and temperature and remained constant at high frequencies. The obtained results indicate that the BPCP 1-3 compounds are non-conductive.Bu çalışmada, yan grup olarak flor bulunan kalkonsübstitüesiklotrifosfazen bileşiklerinin dielektrik ve termal özelliklerinin belirlenmesi amaçlanmıştır. Bu amaçla ilk olarak 4'-hidroksiasetofenon ile 2- florobenzaldehit (a), 3-florobenzaldehit (b)ve 4-florobenzaldehit (c)NaOH varlığında etanol çözücüsünde etkileştirilerek 4'-hidroksi-sübstitüekalkon bileşikleri (1a-c) sentezlendi. İkinci olarak hekzaklorosiklotrifosfazen(HCP) ile 2,2'-dioksibifenolün reaksiyonundan 2,2-dikloro-4,4,6,6-[spiro(2',2''- dioksi-1',1''-bifenilil)]siklotrifosfazen (DPP) bileşiği elde edildi. Daha sonra sentezlenen 1a-c bileşikleri ileDPP bileşiği reaksiyona sokularak kalkonsübstitüesiklotrifosfazen bileşikleri (BPCP 1-3) sentezlendi.Sübstitüesiklotrifosfazen bileşiklerinin yapıları FT-IR, 1H, 13C-APT ve 31P-NMR spektroskopi yöntemleri ile doğrulandı ve bileşiklerin termal davranışları DSC ve TGA termal analiz metotları ile belirlendi. TGA sonuçları bileşiklerin yüksek sıcaklıklarda bile kararlı bir yapıya sahip olduğunu göstermiştir. Sentezleri gerçekleştirilen bu fosfazen bileşiklerinin (BPCP 1-3)dielektrik sabiti, dielektrik kayıp faktörü ve AC iletkenlik değerleri artan sıcaklığa karşı frekansın bir fonksiyonu olarak (100 Hz ile 30 kHz arasında) empedans analizörü ile belirlendi. BPCP 1-3 bileşiklerinin artan frekans ile dielektrik özellikleri değiştiği gözlendi. Ayrıca bileşiklerin kapasitans ve dielektrik sabiti değerleri artan frekans ve sıcaklıkta azalmakta ve yüksek frekanslarda sabit kaldığı gözlendi. Elde edilen sonuçlar neticesinde BPCP 1-3 bileşiklerinin yalıtkan özellik gösterdiği tespit edildi

2,2-Bis(2-Formilfenoksi)-4,4,6,6-Bis(Spiro(2',2''-Dioxy-1',1''-Bifenilil))Siklotrifosfazenin Schiff bazı türevlerinin sentezi ve karakterizasyonu

Hekzaklorosiklotrifosfazen (1) ile 2,2'-bifenol argon atmosferinde reaksiyona sokularak 2,2'-dikloro-4,4,6,6-bis(spiro(2',2''-dioksi-1',1''-bifenilil))siklotrifosfazen (2) bileşiği elde edildi. 2 bileşiği 2-hidroksibenzaldehit ile K2CO3’lı ortamda etkileştirilerek 2,2-bis(2-formilfenoksi)-4,4,6,6-bis(spiro(2',2''-dioksi-1',1''-bifenilil))siklotrifosfazen (3) bileşiği elde edildi. Elde edilen 3 bileşiği aromatik primer aminlerle (Ar-NH2 veya Ar-CH2-NH2) etkileştirilerek Schiff Bazı taşıyan siklotrifosfazen bileşikleri (4-11) elde edildi. 2,2-bis(2-formilfenoksi)-4,4,6,6-bis(spiro(2',2''-dioksi-1',1''-bifenilil))siklotrifosfazen (3) bileşiği sırasıyla 4-metoksibenzilamin, 2-klorobenzilamin, 4-klorobenzilamin, R-(+)-1-(2-naftil)etilamin, 2-hidrosifenilamin, 4-hidrosifenilamin, 4-nitrilfenilamin, 2-fenilfenilamin, 2-amino-4-klorofenol ve 2-aminopirimidin-kullanılmıştır. Elde edilen ürünlerin yapıları FT-IR, (1H, 13C, 31P) NMR ve elementel analiz ile aydınlatıldı.In this study, hexachlorocylotriphosphazene (1) was reacted with biphenyl-2,2'-diol. From this reaction, 2,2-dichloro-4,4,6,6-bis(spiro(2',2''-dioxy-1',1''-bifenilyl))cyclotriphosphazene (2) was obtained. Since hexachlorocylotriphosphazene is sensitive to air and moisture, experimental studies were carried out at without air and moisture in argon atmosphere. 2,2-bis(2-formilphenoxy)-4,4,6,6-bis(spiro(2',2''-dioxy-1',1''-bifenilyl))cyclotriphosphazene (3) was synthesized from the reaction of (2) with 2-hydroxybenzaldehyde Schiff Base containing compounds (4-13) were synthesized by the reaction of 2,2-bis(2-formilphenoxy)-4,4,6,6-bis(spiro(2',2''-dioxy-1',1''-bifenilyl))cyclotriphosphazene (3) with 4-methoxy benzylamine, 2-chloro-benzylamine, 4-chlorobenzylamine, 2-naphthylethylamine, 2-hydroxyphenylamine, 4-hydroxyphenylamine, 4-nitrilephenylamine, 2-phenylphenylamine, 2-hydroxy-4-chlorophenylamine and 2-aminopyrimidine respectively. The structures of the compounds were characterized by FT-IR, (1H, 13C and 31P) NMR spectroscopy and elemental analysis

Synthesis, structural characterization and dielectric behavior of new oxime-cyclotriphosphazene derivatives

The cyclotriphosphazene compound (2) bearing formyl groups as side groups was obtained from the reaction of 2,2-Dichloro-4,4,6,6-bis[spiro(2′,2″-dioxy-1′,1″-biphenylyl)]cyclotriphosphazene (1) with 4-hydroxy-3-methoxybenzaldehyde in the presence K2CO3 in tetrahydrofuran. Oxime-cyclotriphosphazene compound (3) was synthesized from the reaction of compound 2 with hydroxylamine hydrochloride in pyridine. The synthesized oxime-phosphazene compound (3) was reacted with alkyl and acyl halides. As a results, the cyclotriphosphazene compounds (1–10) bearing oxime ether and ester as side groups were obtained. The chemical structures of these compounds (1–10) were determined by elemental analysis, FT-IR, 1H, 13C and 31P NMR spectroscopic methods. Dielectric constant, dielectric loss factors and conductivity properties of cyclotriphosphazene compounds were measured over the frequency range from 100 Hz to 2 kHz at 25 °C and compared with each other. It is found that ester substituted cyclotriphosphazenes have higher dielectric constant. Our study suggests that these phosphazenes promising candidate materials in multifunctional optoelectronic devices.Sponsor Kurum: Fırat Üniversitesi Finansman Kodu: FF.11.2

Synthesis, characterization, and biological evaluation of new oxime-phosphazenes

Hexachlorocylotriphosphazene (1) was reacted with 4-hydroxy-3-methoxybenzaldehyde to give hexakis[(4-formyl-2-methoxy)phenoxy]cyclotriphosphazene (2). Hexakis[(4-(hydroxyimino)2-methoxy)phenoxy]cyclotriphosphazene (3) was synthesized by reaction of 2 with hydroxlamine hydrochloride in pyridine. Compound 3 was reacted with benzyl chloride, acetyl chloride, allyl bromide, benzoyl chloride, propanoyl chloride, 4-methoxybenzoyl chloride, 2-chlorobenzoyl chloride, chloroacetyl chloride, methyl iodide, and thiophene-2-carbonyl chloride. From these reactions, full or partially substituted compounds were obtained, usually in high yields. Pure or defined products could not be obtained from reaction of 3 with methacryloyl chloride and O-acetylsalicyloyl chloride. The structures of the compounds were determined by elemental analysis, and IR, 1H, 13C, and 31P NMR spectroscopy. The synthesized compounds were screened for in-vitro antimicrobial activity against two Gram-positive bacteria (Staphylococcus aureus and Enterococcus faecalis), two gram-negative bacteria (Escherichia coli and Klebsiella pneumonia), and fungal strains (Aspergillus niger, and Candida albicans) by the agar well diffusion method. Few compounds had significant activity against both Gram-positive and Gram-negative bacteria. None of the compounds had antifungal activity except compounds 7 and 9, which had moderate activity.Sponsor Kurum Adı: Fırat Üniversitesi Finansman Kodu: FF.11.0

Synthesis, structural characterization and anti-carcinogenic activity of new cyclotriphosphazenes containing dioxybiphenyl and chalcone groups

2,2-Dichloro-4,4,6,6-bis[spiro(2′,2″-dioxy-1′,1″-biphenylyl]cyclotriphosphazene (2) was synthesized from hexachlorocyclotriphosphazene (HCCP) and 2,2′-dihydroxybiphenyl. The mixed substituent chalcone/dioxybiphenyl cyclophosphazenes (2a–h) were obtained from the reactions of (2) with hydroxy chalcone compounds in K2CO3/acetone system. The chalcone-cyclophosphazene compounds were characterized by elemental analysis, FT-IR, 1H, 13C, 31P NMR techniques. In vitro anti-carcinogenic activities of all compounds were determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Anti-carcinogenic activity of the compounds (2a–h) against androgen-dependent (LNCaP) and independent (PC-3) human prostate cancer cell lines were investigated. Our results indicate that the chalcone-phosphazene compounds (2a–h) have anti-carcinogenic activity on PC-3 and LNCaP cell lines (p < 0.05). The effective dose of the compounds was determined as 100 μM.Fırat Üniversites

Synthesis of 2-(2,3,4-trimethoxyphenyl)-1-(substituted-phenyl)acrylonitriles: In vitro anticancer activity against MCF-7, PC-3 and A2780 cancer cell lines

A series of 2-(2,3,4-trimethoxyphenyl)-1-(substituted-phenyl)acrylonitrile (2–9) were designed and synthesized to develop new cancer drugs. The structures of synthesized compounds 2–9 were described by using melting point, mass (MALDI-TOF-MS), FT-IR, elemental analysis, 1H, 13C, 13C-APT and 2D NMR spectroscopy. The in vitro anticancer activities of 2–9 against human breast cancer (MCF-7), human prostate cancer (PC-3) and human ovarian cancer cells (A2780) were investigated by [3-(4,5-dimethylthiazol)-2-yl]-2,5-diphenyl-2H-tetrazolium bromide] (MTT) assay method. Additionally, the LogIC50 values of these compounds on A2780, MCF-7 and PC-3 cell lines were calculated by using inhibition % values by the GraphPad Prism 6 program on a computer. The results indicated that these compounds have high anticancer activity against MCF-7, PC-3 and A2780 cell lines (especially A2780 cell lines, p < 0.05).Sponsor Kuruluş: TÜBİTAK Finansman Kodu: 110T65

Eu+3-doped chalcone substituted cyclotriphosphazenes: Synthesis, characterizations, thermal and dielectrical properties

A series of new cyclotriphosphazene derivatives (2a-e) were prepared from the reactions of substituted chalcone compounds (1a-e) containing different organic side groups at para position with cyclotriphosphazene (2) bearing dioxybiphenyl. The structures of 2a-e were approved by microanalysis and spectroscopic techniques (MS, FT-IR, 31P, 1H, 13C, and 13C-APT NMR). The thermal behaviors of compounds 2a-e were investigated by thermogravimetric analysis (TGA). These compounds were found to be stable up to about 300 °C. Dielectric properties of 2a-e were measured against temperature (between 25 and 160 °C at 1 kHz) and frequency (range from 100 Hz to 5 kHz at 25 °C) using means of an impedance analyzer. Among them dielectric properties of methoxy substituted cyclotriphosphazene 2e were found to be higher than other phosphazenes. The compound 2b, which has the lower dielectric property values than other phosphazenes, was selected to determine the influence of Eu+3-doping on the dielectric properties of phosphazenes and doped with Eu+3 at different mole ratios. At the dielectric properties of Eu+3-doped compound 2b (with increasing molar ratios of Eu+3) was observed an excellent increasing according to Eu+3-undoped phosphazene compounds.Sponsor Kurum: Fırat Üniversitesi Finansman Kodu: FF.12.1

Synthesis, characterization and dielectric properties of phosphazenes containing chalcones

The new hexasubstitue-cyclophosphazene compounds containing chalcone derivatives (2–11) were obtained from the reactions of hexachlorocyclotriphosphazene (1) with several hydroxy chalcones in K2CO3/acetone system. All products were generally obtained in high yields. The structures of the compounds were defined by elemental analysis, FT-IR, 1H, 13C and 31P NMR spectroscopy. Dielectric measurements for phosphazenes containing chalcone compounds (5–8) were carried out by means of an impedance analyzer as a function of temperature and frequency. Dielectric properties of samples prepared in a plate form were measured at room temperature over the frequency range 50 Hz to 2 kHz and given as compared with each other

(E)-1-(4-Hydroxyphenyl)-3-(substituted-phenyl)prop-2-en-1-ones: Synthesis, In Vitro Cytotoxic Activity and Molecular Docking Studies

A series of chalcone compounds (2–11) were designed and synthesized to determine their cytotoxic effects. The structures of 2–11 were fully characterized by their physical and spectral data. The in vitro cytotoxic effects of 2–11 were evaluated against human ovarian cancer (A2780), breast cancer (MCF-7) and prostate cancer (PC-3 and LNCaP) cell lines. The activity potentials of compounds were further evaluated through molecular docking studies with AutoDock4 and Vina softwares. All the compounds (except compound 5) showed significant cytotoxic effects at high doses in all cancer cell lines. Among all the compounds studied, one compound i.e. compound 2 demonstrated dose-dependent activity, particularly against A2780/LNCaP cancer cell lines. The most effective compounds 8, 9, 10 and 11 reduced the cell viability of A2780, MCF-7, PC-3 and LNCaP cells by 50–98%, while other compounds 2, 4 and 7 reduced the cell viability of A2780 cells by 70–90% at concentrations of 50 and 100 µM

Design and fabrication of dioxyphenylcoumarin substituted cyclotriphosphazene compounds photodiodes

The present study introduces cyclotriphosphazene compounds substituted by dioxyphenylcoumarin as a photodiode application. Firstly, 7,8-dihydroxy-3-(3-methylphenyl)coumarin (1b) has been obtained by conventional as well as microwave assisted methods. Novel optoelectronic device characteristics for both mono and disubstituted dioxyphenylcoumarin bearing cyclotriphosphazene compounds (HCP-2 and HCP-4) have been synthesized from the reactions of cyclotriphosphazene containing dioxybiphenyl (HCP-1 and HCP-3) with compound 1b, respectively. The structures of compounds HCP 1–4 were identified by using elemental analysis, 1H, 13C-APT, 31P NMR and 2D HETCOR NMR and FT-IR spectroscopy methods. The Al/HCP-2/p-Si/Al and Al/HCP-4/-p-Si/Al photodiodes properties have been investigated from current-voltage (I−V) and capacitance-voltage (C−V) measurements. The electrical parameters of the prepared diodes such as ideality factor n and series resistance Rs were investigated in dark and at room temperature from (I−V) curve and Nord's method. As can be seen, the Al/HCP-2/p-Si/Al diode of high rectification ratio RR and with ideality factor greater than unity. The influence of light illuminations on the diode shows that the device can be used as photodiode with good efficiency. The barrier height ϕb and series resistance Rs have been calculated from the capacitance-voltage (C−V)and conductance-voltage (G−V) measurements under various applied frequencies from 10 kHz to 1 MHz. the high difference in the results of barrier height obtained from I-V and C-V calculations confirm the influence of series resistance and localized states on transport of charge carriers and the photodiode performance.TUBITAK-110T652 Fırat University, FÜBAP-FF.161