Advertisement

Ionics

pp 1–12 | Cite as

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

  • Ali Destegül
  • Hüseyin Akbaş
  • Ahmet KaradağEmail author
  • Betül Canımkurbey
  • Yusuf Yerli
  • Kadir Cihan Tekin
  • Uğur Malayoğlu
  • Zeynel Kılıç
Original Paper
  • 31 Downloads

Abstract

Three new fully substituted starting materials (Pz1-3) were synthesized reacting dimethylaminoethanol, 3-dimethylamino-1-propanol, and 4-pyrridinemethanol, which were saltified using metallic sodium, with partly substituted phosphazene (Pz) compound. Phosphazene-based ionic liquids (PzILs), PzIL1-3, were obtained from the reaction of the starting materials with CH3I. New ionic liquids (PzIL1a-3a) were obtained by replacing the I ions of these ionic liquids with the NTf2 anions. The structures of PzILs were elucidated by elemental analysis, FTIR, and 1H, 13C {1H}, and 31P {1H} NMR techniques. The thermal properties of all compounds were investigated using thermogravimetric (TG) analysis. Compared with the output materials, the thermal stability of the ionic liquids was found to be higher, 160, 199, and 228 °C for PzIL1-3 respectively, and 270, 204, and 287 °C for PzIL1a-3a respectively. At the same time, the viscosity measurements of PzIL1a-3a compounds obtained as liquids in room temperature were measured with a cone/plate viscometer. It is understood from the viscosity values that the fluidities of these compounds are as low as 864, 3801, and 423,700 cP, respectively (water viscosity is 0.7977 cP at 30 °C). In addition to these studies, sliding wear test was conducted at room temperature using AA7075 disc specimen against the stationary 100Cr6 steel ball. The wear protection of PzILs was determined considering the volume loss of AA7075.

Keywords

Phosphazene Phosphazene-based ionic liquid Tribology Organic field-effect transistor 

Notes

Funding information

We thank the Scientific and Technical Research Council of Turkey (TUBİTAK, Grant KBAG-114Z740; COST Action CM 1206) for financial support. The author Z. K. thanks to Turkish Academy of Sciences (TÜBA) for the partial support of this study.

Supplementary material

11581_2019_2846_MOESM1_ESM.pdf (1.2 mb)
ESM 1 (PDF 1236 kb)

References

  1. 1.
    Koran K, Ozen F, Torğut G, Pıhtılı G, Çil E, Görgülü AO, Arslan M (2014) Synthesis, characterization and dielectric properties of phosphazenes containing chalcones. Polyhedron 79:213–220.  https://doi.org/10.1016/j.poly.2014.04.070 CrossRefGoogle Scholar
  2. 2.
    Ozay H, Ozay O (2014) Synthesis and characterization of drug microspheres containing phosphazene for biomedical applications. Colloids and Surfaces A: Physicochem Eng Aspect 450:99–105.  https://doi.org/10.1016/j.colsurfa.2014.03.022 CrossRefGoogle Scholar
  3. 3.
    Sun J, Yu Z, Wang X, Wu D (2014) Synthesis and performance of cyclomatrix polyphosphazene derived from trispiro-cyclotriphosphazene as a halogen-free nonflammable material. ACS Sustainable Chem Eng 2:231–238.  https://doi.org/10.1021/sc400283d CrossRefGoogle Scholar
  4. 4.
    Davarcı D, Beşli S, Demirbaş E (2013) Synthesis of a series of triple-bridged cyclotriphosphazene hexa-alkoxy derivatives and investigation of their structural and mesomorphic properties. Liq Cryst 40(5):624–631.  https://doi.org/10.1080/02678292.2013.773093 CrossRefGoogle Scholar
  5. 5.
    He Q, Dai H, Tan X, Cheng X, Liu F, Tschierskec C (2013) Synthesis and characterization of room temperature columnar mesogens of cyclotriphosphazene with Schiff base units. J Mater Chem C 1(43):7148–7154.  https://doi.org/10.1039/C3TC31371A CrossRefGoogle Scholar
  6. 6.
    Wang X, Tan AYX, Cho CM, Ye Q, He C, Ji R, Xie HQ, Tsai JWH, Xu J (2015) Highly thermally stable cyclotriphosphazene based perfluoropolyether lubricant oil. Trib Int 90:257–262.  https://doi.org/10.1016/j.triboint.2015.04.018 CrossRefGoogle Scholar
  7. 7.
    Song Z, Liang Y, Fan M, Zhou F, Liu W (2014) Lithium-based ionic liquids functionalized by sym-triazine and cyclotriphosphazene as high temperature lubricants. Trib Int 70:136–141.  https://doi.org/10.1016/j.triboint.2013.09.025 CrossRefGoogle Scholar
  8. 8.
    Inoue K, Yamauchi T, Itoh T, Ihara EJ (2007) Ionic conductivity of cross-linked polymethacrylate derivatives/cyclophosphazenes/Li+ salt complexes. Inorg Organomet Polym Mater 17(2):367–375.  https://doi.org/10.1007/s10904-007-9126-3 CrossRefGoogle Scholar
  9. 9.
    Ahn S, Kim HS, Yang S, Do JY, Kim BH, Kim K (2009) Thermal stability and performance studies of LiCo1/3Ni1/3Mn1/3O2 with phosphazene additives for Li-ion batteries. J Electroceram 23:289–294.  https://doi.org/10.1007/s10832-008-9437-y CrossRefGoogle Scholar
  10. 10.
    Nishimoto T, Yasuda T, Lee SY, Kondo R, Adachi C (2014) A six-carbazole-decorated cyclophosphazene as a host with high triplet energy to realize efficient delayed-fluorescence OLEDs. Mater Horiz 1:264–269.  https://doi.org/10.1039/C3MH00079F CrossRefGoogle Scholar
  11. 11.
    Schrögel P, Hoping M, Kowalsky W, Hunze A, Wagenblast G, Lennartz C, Strohriegl P (2011) Phosphazene-based host materials for the use in blue phosphorescent organic light-emitting diodes. Chem Mater 23:4947–4953.  https://doi.org/10.1021/cm201940f CrossRefGoogle Scholar
  12. 12.
    Chandrasekhar V, Thilagar P, Pandian BM (2007) Cyclophosphazene-based multi-site coordination ligands. Coord Chem Rev 251:1045–1074.  https://doi.org/10.1016/j.ccr.2006.07.005 CrossRefGoogle Scholar
  13. 13.
    Li X, Jiang F, Chen L, Wu M, Chen Q, Bu Y, Hong M (2012) Three novel 3D coordination polymers based on a flexible multisite cyclotetraphosphazene ligand. Dalton Trans 41(46):14038–14041.  https://doi.org/10.1039/C2DT31852K CrossRefGoogle Scholar
  14. 14.
    Çıralı DE, Uyar Z, Koyuncu İ, Hacıoğlu N (2015) Synthesis, characterization and catalytic, cytotoxic and antimicrobial activities of two novel cyclotriphosphazene-based multisite ligands and their Ru (II) complexes. Appl Organomet Chem 29:536–542.  https://doi.org/10.1002/aoc.3328 CrossRefGoogle Scholar
  15. 15.
    Asmafiliz N, Kılıç Z, Öztürk A, Süzen Y, Hökelek T, Açık L, Çelik ZB, Koç LY, Yola ML, Üstündağ Z (2013) Phosphorus-nitrogen compounds: Part 25. Syntheses, spectroscopic, structural and electrochemical ınvestigations, antimicrobial activities, and DNA ınteractions of ferrocenyldiaminocyclotriphosphazenes. Phosphorus Sulfur Silicon Relat Elem 188(12):1723–1742.  https://doi.org/10.1080/10426507.2013.779273 CrossRefGoogle Scholar
  16. 16.
    Başterzi NS, Koçak SB, Okumuş A, Kılıç Z, Hökelek T, Çelik Ö, Türk M, Koç LY, Açık L, Aydın B, Dal H (2015) Syntheses, structural characterization and biological activities of spiro-ansa-spiro-cyclotriphosphazenes. New J Chem 39:8825–8839.  https://doi.org/10.1039/C5NJ01530H CrossRefGoogle Scholar
  17. 17.
    Okumuş A, Elmas G, Kılıç Z, Ramazanoğlu N, Açık L, Türk M, Akca G (2017) The reactions of N3P3Cl6 with monodentate and bidentate ligands: the syntheses and structural characterizations, in vitro antimicrobial activities, and DNA interactions of 4-fluorobenzyl(N/O)spirocyclotriphosphazenes. Turk J Chem 41:525–547.  https://doi.org/10.3906/kim-1612-80 CrossRefGoogle Scholar
  18. 18.
    Asmafiliz N, Kılıç Z, Hökelek T, Koç LY, Açık L, Süzen Y, Öner Y (2013) Phosphorus-nitrogen compounds: Part 26. Syntheses, spectroscopic and structural ınvestigations, biological and cytotoxic activities, and DNA ınteractions of mono and bisferrocenylspirocyclotriphosphazenes. Inorg Chim Acta 400:250–261.  https://doi.org/10.1016/j.ica.2013.03.001 CrossRefGoogle Scholar
  19. 19.
    Asmafiliz N, Kılıç Z, Civan M, Avcı O, Gönder LY, Açık L, Aydın B, Türk M, Hökelek T (2016) Phosphorus–nitrogen compounds. Part 36. Syntheses, Langmuir–Blodgett thin films and biological activities of spiro-bino-spiro trimeric phosphazenes. New J Chem 40:9609–9626.  https://doi.org/10.1039/C6NJ02052F CrossRefGoogle Scholar
  20. 20.
    Akbaş H, Okumuş A, Karadağ A, Kılıç Z, Hökelek T, Koç LY, Açık L, Aydın B, Türk M (2016) 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.  https://doi.org/10.1007/s10973-015-5001-6 CrossRefGoogle Scholar
  21. 21.
    Gering KL, Harrup MK, Rollins HW (2015) Ionic liquids, electrolyte solutions including the ionic liquids, and energy storage devices including the ionic liquids. US Patent 9206210B2Google Scholar
  22. 22.
    Li J, Feng D, Liang Y, Xia Y, Liu W (2010) Synthesis and tribological behavior of ionic liquid substituted fluoroalkoxycyclophosphazene derivatives in steel-steel contacts. Ind Lub Trib 62(3):161–167.  https://doi.org/10.1108/00368791011034548 CrossRefGoogle Scholar
  23. 23.
    Akbaş H, Karadağ A, Aydın A, Destegül A, Kılıç Z (2017) 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.  https://doi.org/10.1016/j.molliq.2017.01.067 CrossRefGoogle Scholar
  24. 24.
    Okumuş A, Akbaş H, Karadağ A, Aydın A, Kılıç Z, Hökelek T (2017) Antiproliferative effects against A549, Hep3B and FL cell lines of cyclotriphosphazene-based novel protic molten salts: spectroscopic, crystallographic and thermal results. Chem Select 2:4988–4999.  https://doi.org/10.1002/slct.201700497 Google Scholar
  25. 25.
    Lee J, Han AR, Kim J, Kim Y, Oh JH, Yang C (2012) Solution-processable ambipolar diketopyrrolopyrrole–selenophene polymer with unprecedentedly high hole and electron mobilities. J Am Chem Soc 134(51):20713–20721.  https://doi.org/10.1021/ja308927g CrossRefGoogle Scholar
  26. 26.
    Ono S, Seki S, Hirahara R, Tominari Y, Takeya J (2008) High-mobility, low-power, and fast-switching organic field-effect transistors with ionic liquids. Appl Phys Lett 92(10):103313–103315.  https://doi.org/10.1063/1.2898203 CrossRefGoogle Scholar
  27. 27.
    Chen FF, Huang K, Zhou Y, Tian ZQ, Zhu X, Tao DJ, Jiang DE, Dai S (2016) Multi-molar absorption of CO2 by the activation of carboxylate groups in amino acid ionic liquids. Angew Chem Int Ed 55(25):7161–7170.  https://doi.org/10.1002/anie.201602919 CrossRefGoogle Scholar
  28. 28.
    Tao DJ, Chen FF, Tian ZQ, Huang K, Mahurin SM, Jiang DE, Dai S (2017) Highly efficient carbon monoxide capture by carbanion-functionalized ionic liquids through C-site interactions. Angew Chem Int Ed 129(124):6947–6951.  https://doi.org/10.1002/ange.201701919 CrossRefGoogle Scholar
  29. 29.
    Chen FF, Huang K, Fan JP, Tao DJ (2018) Chemical solvent in chemical solvent: a class of hybrid materials for effective capture of CO2. AICHE J 64(2):632–639.  https://doi.org/10.1002/aic.15952 CrossRefGoogle Scholar
  30. 30.
    Zhou F, Liang Y, Liu W (2009) Ionic liquid lubricants: designed chemistry for engineering applications. Chem Soc Rev 38:2590–2599.  https://doi.org/10.1039/B817899M CrossRefGoogle Scholar
  31. 31.
    González R, Bartolomé M, Blanco D, Viesca JL, Fernández-González A, Battez AH (2016) Effectiveness of phosphonium cation-based ionic liquids as lubricant additive. Trib Int 98:82–93.  https://doi.org/10.1016/j.triboint.2016.02.016 CrossRefGoogle Scholar
  32. 32.
    Qu J, Bansal DG, Yu B, Howe JY, Luo H, Dai S, Li H, Blau PJ, Bunting BG, Mordukhovich G, Smolenski DJ (2012) Antiwear performance and mechanism of an oil-miscible ionic liquid as a lubricant additive. ACS Appl Mater Inter 4:997–1002.  https://doi.org/10.1021/am201646k CrossRefGoogle Scholar
  33. 33.
    Mu Z, Liu W, Zhang S, Zhou F (2004) Functional room-temperature ionic liquids as lubricants for an aluminum-on-steel system. Chem Lett 33:524–525.  https://doi.org/10.1246/cl.2004.524 CrossRefGoogle Scholar
  34. 34.
    Mu Z, Zhou F, Zhang S, Liang Y, Liu W (2005) Effect of the functional groups in ionic liquid molecules on the friction and wear behavior of aluminum alloy in lubricated aluminum-on-steel contact. Trib Int 38(8):725–731.  https://doi.org/10.1016/j.triboint.2004.10.003 CrossRefGoogle Scholar
  35. 35.
    Jiménez AE, Bermúdez MD, Iglesias P, Carrión FJ, Martínez-Nicolás G (2006) 1-N-Alkyl -3-methylimidazolium ionic liquids as neat lubricants and lubricant additives in steel–aluminium contacts. Wear 260(7–8):766–782.  https://doi.org/10.1016/j.wear.2005.04.016 CrossRefGoogle Scholar
  36. 36.
    Jiménez AE, Bermúdez MD, Carrión FJ, Martínez-Nicolás G (2006) Room temperature ionic liquids as lubricant additives in steel–aluminium contacts: influence of sliding velocity, normal load and temperature. Wear 261(3–4):347–359.  https://doi.org/10.1016/j.wear.2005.11.004 CrossRefGoogle Scholar
  37. 37.
    Liu X, Zhou F, Liang Y, Liu W (2006) Tribological performance of phosphonium based ionic liquids for an aluminum-on-steel system and opinions on lubrication mechanism. Wear 261(10):1174–1179.  https://doi.org/10.1016/j.wear.2006.03.018 CrossRefGoogle Scholar
  38. 38.
    Jiménez AE, Bermúdez MD (2007) Ionic liquids as lubricants for steel–aluminum contacts at low and elevated temperatures. Trib Lett 26(1):53–60.  https://doi.org/10.1007/s11249-006-9182-9 CrossRefGoogle Scholar
  39. 39.
    Mu Z, Wang X, Zhang S, Liang Y, Bao M, Liu W (2008) Investigation of tribological behavior of Al–Si alloy against steel lubricated with ionic liquids of 1-diethylphosphonyl-n-propyl-3-alkylimidazolium tetrafluoroborate. J Trib 130(3):034501–034505.  https://doi.org/10.1115/1.2913553 CrossRefGoogle Scholar
  40. 40.
    Jiménez AE, Bermúdez MD (2008) Imidazolium ionic liquids as additives of the synthetic ester propylene glycol dioleate in aluminium–steel lubrication. Wear 265(5–6):787–798.  https://doi.org/10.1016/j.wear.2008.01.009 CrossRefGoogle Scholar
  41. 41.
    Omotowa BA, Phillips BS, Zabinski JS, Shreeve JM (2004) Phosphazene-based ionic liquids: synthesis, temperature-dependent viscosity, and effect as additives in water lubrication of silicon nitride ceramics. Inor Chem 43(17):5466–5471.  https://doi.org/10.1021/ic049483o CrossRefGoogle Scholar
  42. 42.
    Akbas H, Okumus A, Kılıc Z, Hökelek T, Süzen Y, Koc LY, Açık L, Çelik ZB (2013) 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. Europ J Med Chem 70:294–307.  https://doi.org/10.1016/j.ejmech.2013.09.046 CrossRefGoogle Scholar
  43. 43.
    Eswara AT (2014) MHD boundary layers due to a point sink with temperature-dependent viscosity/prandtl number. Int J Mod Opt 4(5):350–353.  https://doi.org/10.7763/IJMO.2014.V4.399 Google Scholar
  44. 44.
    Luan S, Neudeck GW (1992) An experimental study of the source/drain parasitic resistance effects in amorphous silicon thin film transistors. J Appl Phys 72(2):766–772.  https://doi.org/10.1063/1.351809 CrossRefGoogle Scholar
  45. 45.
    Minari T, Nemoto T, Isoda S (2006) Temperature and electric-field dependence of the mobility of a single-grain pentacene field-effect transistor. J Appl Phys 99(3):034506–034510.  https://doi.org/10.1063/1.2169872 CrossRefGoogle Scholar
  46. 46.
    Kraus M, Haug S, Brütting W, Opitz A (2011) Achievement of balanced electron and hole mobility in copper-phthalocyanine field-effect transistors by using a crystalline aliphatic passivation layer. Org Elect 12(5):731–735.  https://doi.org/10.1016/j.orgel.2011.02.001 CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  • Ali Destegül
    • 1
  • Hüseyin Akbaş
    • 1
  • Ahmet Karadağ
    • 1
    • 2
    Email author
  • Betül Canımkurbey
    • 3
  • Yusuf Yerli
    • 4
  • Kadir Cihan Tekin
    • 5
  • Uğur Malayoğlu
    • 6
  • Zeynel Kılıç
    • 6
  1. 1.Department of ChemistryGaziosmanpaşa UniversityTokatTurkey
  2. 2.Department of BiotechnologyBartın UniversityBartınTurkey
  3. 3.Department of PhysicsAmasya UniversityAmasyaTurkey
  4. 4.Department of PhysicsYıldız Technical UniversityIstanbulTurkey
  5. 5.Department of Metallurgical and Materials EngineeringDokuz Eylül UniversityİzmirTurkey
  6. 6.Department of ChemistryAnkara UniversityAnkaraTurkey

Personalised recommendations