2,2-(3-(Sübstitüe-florofenil)-1-(4-oksifenil)prop-2-en-1-one)-4,4,6,6- bis[spiro(2',2"-dioksi-1',1"-bifenilil]SiklotrifosfazenlerinDielektrik ve Termal Özellikleri

Bu çalışmada, yan grup olarak flor bulunan kalkonsübstitüesiklotrifosfazen bileşiklerinin dielektrik vetermal özelliklerinin belirlenmesi amaçlanmıştır. Bu amaçla ilk olarak 4'-hidroksiasetofenon ile 2-florobenzaldehit (a), 3-florobenzaldehit (b)ve 4-florobenzaldehit (c)NaOH varlığında etanolçözücüsünde etkileştirilerek 4'-hidroksi-sübstitüekalkon bileşikleri (1a-c) sentezlendi. İkinci olarakhekzaklorosiklotrifosfazen(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 bileşikleriileDPP bileşiği reaksiyona sokularak kalkonsübstitüesiklotrifosfazen bileşikleri (BPCP 1-3)sentezlendi.Sübstitüesiklotrifosfazen bileşiklerinin yapıları FT-IR, 1 H, 13 C-APT ve 31 P-NMR spektroskopiyöntemleri ile doğrulandı ve bileşiklerin termal davranışları DSC ve TGA termal analiz metotları ilebelirlendi. TGA sonuçları bileşiklerin yüksek sıcaklıklarda bile kararlı bir yapıya sahip olduğunugöstermiştir. Sentezleri gerçekleştirilen bu fosfazen bileşiklerinin (BPCP 1-3)dielektrik sabiti, dielektrikkayıp faktörü ve AC iletkenlik değerleri artan sıcaklığa karşı frekansın bir fonksiyonu olarak (100 Hz ile 30kHz arasında) empedans analizörü ile belirlendi. BPCP 1-3 bileşiklerinin artan frekans ile dielektriközellikleri değiştiği gözlendi. Ayrıca bileşiklerin kapasitans ve dielektrik sabiti değerleri artan frekans vesıcaklıkta azalmakta ve yüksek frekanslarda sabit kaldığı gözlendi. Elde edilen sonuçlar neticesinde BPCP1-3 bileşiklerinin yalıtkan özellik gösterdiği tespit edildi.

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, 1 H, 13 C-APT and 31 P-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

PDF

___

Allcock, H.R., 1972. Phosphorus-Nitrogen Compounds.Cyclic, Linear, and High Polymeric Systems. Academic Press Inc. New York.
Akbaş, H., Karadağ, A., Aydın, A., Destegül, A., Kılıç, Z., 2017. Synthesis, structuralandthermalproperties of thehexapyrrolidinocyclotriphosphazenes- basedproticmoltensalts: Antiproliferativeeffectsagainst HT29, HeLa, and C6 cancercelllines.Journal of MolecularLiquids, 230, 482- 495.
Akbas, H., Okumus, A., Karadag, A., Kilic, Z., Hokelek, T., Koc, L.Y., Acik, L., Aydin, B., Turk, M., 2016. Phosphorus-Nitrogen compounds part 32. Structural and thermal characterizations, antimicrobial and cytotoxic activities, and in vitro DNA binding of the phosphazenium salts.Journal of Thermal Analysis and Calorimetry,123, 1627-1641.
Biryan, F., Demirelli, K., 2017. Characterization, thermalbehavior, andelectricalmeasurements of poly [4‐(2‐bromoisobutyroylmethyl)styrene].Advances in PolymerTechnology, 1-19.
Brandt, K., Kruszynski, R., Bartzak, T.J. Czomperlik, I.P., 2001. AIDS–related Lymphoma screen results and molecular structure determination of a new crown ether bearing aziridinylcyclophosphazene, potentially capable of ion-regulated DNA cleavage action.Inorg.Chim.Acta.,322, 138-144.
Carriedo,G.A.,Catuxo, L.F., Alonso, F.J.G.,Elipe, P.G., González, P.A., 1996.Preparation of a new type of phosphazene high polymers containing 2,2‘- dioxybiphenyl groups.Macromolecules,29,5320- 5325.
Çoşkun, D., Çoşkun M.F., 2017. KalkonİçerikliÇaprazBağlıPolimerSenteziveAsidikHidr olizi.AKÜ FEMÜBİD, 17(1), 66-72.
Elmas, G., Okumuş, A., Sevinç, P., Kılıç, Z., Açık, L., Atalan, M., Hökelek, T., 2017. Phosphorus- nitrogencompounds. Part 37. Synthesesandstructuralcharacterizations, biologicalactivities of mono andbis (4-fluorobenzyl) spirocyclotetraphosphazenes.New Journal of Chemistry, 41, 5818-5835.
Funiss, B.S.,Hannford, A.J., Smith, P.W.G., Tatchell, A.R., 2004. Vogel’sTextbook of PracticalOrganicChemistry. 5th ed.,Longman, London, 1032–1035.
Gleria, M., Jaeger, R.D., 2004.Phosphazenes a Worldwide Insight. Nova Science Publishers Inc., New York.
Görgülü, A. O., Koran, K., Özen, F., Tekin, S., Sandal, S., 2015. Synthesis, structuralcharacterizationand anti- carcinogenicactivity of newcyclotriphosphazenescontainingdioxybiphenylan dchalconegroups.Journal of MolecularStructure, 1087, 1-10.
İlter, Z., Erol, G., 2016. Asetilbenzofuranmetakrilatblendlerinin termal, elektriksel ve biyolojik özelliklerinin incelenmesi.AKÜ FEMÜBİD,16, 32‐40.
Koran, K., Özen, F., Biryan, F., Demirelli, K., Görgülü, A.O., 2016. Eu+ 3-doped chalconesubstitutedcyclotriphosphazenes: Synthesis, characterizations, thermalanddielectricalProperties.InorganicaChimica Acta, 450, 162-169.
Koran, K., Tekin, Ç., Biryan, F., Tekin, S., Sandal, S., Görgülü, A.O., 2017. Synthesis, structural and thermal characterizations, dielectric properties and in vitro cytotoxic activities of new 2,2,4,4-tetra(4′- oxy-substituted-chalcone)-6,6-diphenylcyclo- triphosphazene derivatives.MedicinalChemistryResearch,26, 962- 974.
Koran, K.,Ozen, F., Torğut, G., Pıhtılı, G., Cil, E., Arslan, M., Görgülü, A.O., 2014. Synthesis, characterizationanddielectricproperties of phosphazenescontainingchalcones.Polyhedron,79, 213-220.
Kuan, J.F., Lin, K.F., 2003. Synthesis of hexa-allylamino- cyclotriphosphazene as a Reactive Fire Retardant For Unsaturated Polyesters.Journal of Applied Polymer Science,91, 697-702.
Liang, W.J.,Li, Y.L., Zhao, P.H., Zhao, G.Z., 2017. Facilesynthesis, spectroscopiccharacterization, andcrystalstructures of dioxybiphenylbridgedcyclotriphosphazenes.Polyhedro n, 129, 30-37.
Liu, R., Wang, X., 2009. Synthesis, characterization, thermal properties and flame retardancy of a novel nonflammable phosphazene-based epoxy resin.Polymer Degradation and Stability,94, 617-624.
Modzelewska, A.,Pettit, C., Achanta, G., Davidson, N.E., Huang, P., Khan,S.R., 2006. Anticanceractivities of novelchalconeandbis-chalconederivatives.Bioorg. Med. Chem., 14, 3491-3495.
Moriya, K., Suzuki, T., Yano, S., Miyajima, S., 2001. 31 P and 13 C NMR studies of a liquid-crystalline cyclotriphosphazene derivative: orientational characteristics and contrasting shielding anisotropies for inorganic and organic moieties.J. Phys. Chem. B,105,7920-7927.
Neamen, D.A., 1997. Semiconductorphysicsanddevices 2nd ed, McGraw-Hill, New York, (420-450, 517-523).
Ozay, H., Yildiz, M., Dulger, B., Unver, H., 2010. Synthesis, spectroscopic studies and antimicrobial sctivity of tetrakis(4-bromo-2- formylphenoxy)cyclotriphosphazene and its imino- amino derivatives.Asian Journal of Chemistry,22, 3813-3823.
Symth, C.P., 1955. Dielectricbehaviourandstructure, McGraw-Hill, New York, 52-61, 202-215.
Şenkuytu, E., Eker, Y., Çiftçi, G.Y., 2017. 4- Hydroxycoumarin functionalizedcyclotriphosphazenes: Synthesis, characterizationandfluorescenceProperties.Inorganic aChimicaActa, 459, 45-50.
Tareev, B., 1975. Physics of dielectricmaterials, Mir Publishers, Moscow.
Torgut, G., Demirelli, K., 2016. Blockcopolymerization of methylmethacrylatevia ATRP methodusing a macroinitiatorproducedby ring openingpolymerization: Characterization, dielectricproperties, and a kineticinvestigation, Journal of MacromolecularScience, Part A.53, 669- 676.
Xu, G.X., Lu, Q., Yu, B.T., Wen, L., 2006. Inorganic polymer phosphazene disulfide as cathode material for rechargeable lithium batteries.Solid State Ionics,177, 305-309.