Novel Aminopyrene Substituted Monospiro/Dispiro Cyclotriphosphazenes: Synthesis, Characterization and Chemosensor Properties

Novel Aminopyrene Substituted Monospiro/Dispiro Cyclotriphosphazenes: Synthesis, Characterization and Chemosensor Properties

In the present work, the novel aminopyrene substituted monospiro/dispirocyclotriphosphazenes (6 and 7) have been synthesized. This compounds were characterized general spectroscopic techniques such as mass, 1H and 31P NMR spectrometry. The photophysical and chemosensor properties toward various metals (Fe3+, Cr3+, Co2+,Al3+, Hg+, Mn2+, Ni2+, Cu2+, Cd2+, Zn2+, Mg2+, Ca2+, Ba2+, Li+, Na+, K+, Cs+) in THF solutionsof aminopyrene substituted compounds were investigated by fluorescence spectroscopy. The metal sensing results showed that compounds 6 and 7 can be candidate fluorescent chemosensors for Cu2+ and Fe3+ ions due to their displaying high selectivity and low limit ofdetection.

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  • Allcock, H.R, Recent advances in phosphazene (phosphonitrilic) chemistry, Chemical Reviews, 1972, 72, 315-356.
  • Chandrasekhar, V, Krishnan, V, Advances in the chemistry of chloro-cyclophosphazenes, Advances in Inorganic Chemistry, 2002, 53, 159-211.
  • Yıldırım, T, Bilgin, K, Yenilmez Çiftçi, G, Tanrıverdi Eçik, E, Şenkuytu, E, Uludağ, Y, Tomak, L, Kılıç, A, Synthesis, cytotoxicity and apoptosis of cyclotriphosphazene compounds as anti-cancer agents, European Journal of Medicinal Chemistry, 2012, 52, 213-220.
  • Bolink, H.J, Barea, E, Costa, R.D., Coronado, E, Sudhakar, S, Zhen, C, Sellinger, A Efficient blue emitting organic light emitting diodes based on fluorescent solution processable cyclic phosphazenes, Organ-ic Electronics, 2008, 9, 155–163.
  • Moriya, K, Masuda, T, Suzuki, T, Yano, S, Kajiwara, M, Liquid Crystalline Phase Transition in Hexakis (4-(N-(41-alkoxyphenyl) iminomethyl) phenoxy) cyclotriphosphazene. Molecular Crystals and Liquid Crystals Science and Technology Section A. Molecular Crys-tals and Liquid Crystals, 1998, 318(1), 267-278.
  • Davarcı, D, Zorlu, Y, Group 12 metal coordination polymers built on a flexible hexakis(3-pyridyloxy)cyclotriphosphazene ligand: Effect of the central metal ions on the construction of coordination polymers, Polyhedron, 2017, 127, 1–8.
  • Şenkuytu, E, Tanrıverdi Eçik, E, Durmuş, M, Yenilmez Çiftçi, G, Monofunctional amines substituted fluorenylidene bridged cyclotri-phosphazenes: ‘Turn-off’ fluorescence chemosensors for Cu2+ and Fe3+ ions, Polyhedron, 2015, 101, 223–229.
  • Yenilmez Çiftçi, G, Şenkuytu, E, Bulut, M, Durmuş, M, Novel Coumarin Substituted Water Soluble Cyclophosphazenes as “Turn-Off” Type Fluorescence Chemosensors for Detection of Fe3+ ions in Aqueous Media, Journal of Fluorescence, 2015, 25, 1819–1830.
  • Kundu, A, Hariharan, P.S, Prabakaran, K, Anthony, S.P, Synthesis of new colori/ A fluorimetric chemosensor for selective sensing of bi-ologically important Fe3+, Cu2+ and Zn2+ metal ions, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2015, 151, 426–431.
  • Li, C.Y, Zou, C.X, Li, Y.F, Tang, J.L, Weng, C, A new rhodamine-based fluorescent chemosensor for Fe3+ and its application in living cell imaging, Dyes and Pigments, 2014, 104, 110-115.
  • Wanga, D, Zheng, J.Q, Zhenga, X.J, Fanga, D.C, Yuanc, D.Q, Jin, L.P, A fluorescent chemosensor for the sequential detection of cop-per(II) and histidine and its biological applications, Sensors and Actu-ators B, 2016, 228, 387–394.
  • Evstatiev, R, Gasche, C, Iron sensing and signalling, Gut, 2012, 61, 933–952.
  • Que, E.L, Domaille, D.W, Chang, C.J, Metals in Neurobiology: Probing Their Chemistry and Biology with Molecular Imaging, Chemical Reviews, 2008, 108, 1517–1549.
  • Andrews, N, Disorders of Iron Metabolism, The New England Jour-nal of Medicine, 1999, 341, 1986–1995.
  • Squittia, R, Ghidoni, R, Simonelli, I, Ivanova, I.D, Colabufo, N.A, Zuin, M, Benussi, L, Binetti, G, Cassetta, E, Rongioletti, M, Siotto, M, Copper dyshomeostasis in Wilson disease and Alzheimer's disease as shown by serum and urine copper indicators, Journal of Trace El-ements in Medicine and Biology, 2018, 45, 181–188.
  • Wang, C, Liu, Y, Cheng, J , Song, J, Zhao, Y, Ye, Y, Efficient FRET-based fuorescen tratiometric chemosensors for Fe3+ and it sap-plication in living cells, Journal of Luminescence, 2015, 157, 143–148.
  • Park, G.J, You, G.R, Choi, Y.W, Kim, C, A naked-eye chemosensor for simultaneous detection of iron and copper ions and its copper complex for colorimetric/fluorescentsensing of cyanide, Sensors and Actuators B, 2016, 229, 257–271.
  • Cheng, P.F, Xu, K.X, Yao, W, Xie, E, Liu, J, Novel fluorescent chemosensors based on carbazole for Cu2+ and Fe3+ in aqueous media, Journal of Luminescence, 2013, 143, 583–586.
  • Carriedo, G.A, Catuxo, L.F, Alonso, F.J.G, Elipe, P.G, Gonzalez, P.A, Preparation of a New Type of Phosphazene High Polymers Con-taining 2,2’-Dioxybiphenyl Groups, Macromolecules, 1996, 29, 5320-5325.
  • Parker, C.A, Rees, W, Correction of Fluorescence Spectra and Meas-urement of Fluorescence Quantum Efficiency, Analyst, 1960, 85(1013), 587-600.