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

Year 2018, Volume: 14 Issue: 2, 209 - 216, 30.06.2018

Elif Şenkuytu

https://doi.org/10.18466/cbayarfbe.399162

Cited By: 3

Abstract

In the present work, the novel aminopyrene
substituted monospiro/dispiro
cyclotriphosphazenes (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 solutions
of 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 of
detection.

Keywords

Cyclotriphosphazene, Monospiro, Dispiro, 1-Aminopyrene, Photophysical Properties

References

• 1. Allcock, H.R, Recent advances in phosphazene (phosphonitrilic) chemistry, Chemical Reviews, 1972, 72, 315-356.
• 2. Chandrasekhar, V, Krishnan, V, Advances in the chemistry of chloro-cyclophosphazenes, Advances in Inorganic Chemistry, 2002, 53, 159-211.
• 3. 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.
• 4. 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.
• 5. 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.
• 6. 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.
• 7. 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.
• 8. 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.
• 9. 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.
• 10. 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.
• 11. 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.
• 12. Evstatiev, R, Gasche, C, Iron sensing and signalling, Gut, 2012, 61, 933–952.
• 13. 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.
• 14. Andrews, N, Disorders of Iron Metabolism, The New England Jour-nal of Medicine, 1999, 341, 1986–1995.
• 15. 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.
• 16. 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.
• 17. 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.
• 18. 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.
• 19. 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.
• 20. Parker, C.A, Rees, W, Correction of Fluorescence Spectra and Meas-urement of Fluorescence Quantum Efficiency, Analyst, 1960, 85(1013), 587-600.