Journals / Turkish Journal of Chemistry / 2020 / Cilt: 44 - Sayı: 1

Nucleophilic substitution reactions of monofunctional nucleophilic reagents with cyclotriphosphazenes containing 2,2-dioxybiphenyl units

Pages
87–98
Publication Date
2022-11-04
DOI
—
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Thestructure of the spiro-(2,2′-dioxybiphenyl)-bis-(anilino)-cyclotriphosphazene (11) was also determined by single-crystalX-ray crystallography.

📌 3 Key Takeaways

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Objective & Hypothesis:The nucleophilic substitution reactions of mono- and bis-spiro-2,2′-dioxybiphenyl cyclotriphosphazenes (3and 4) with cyclopropanemethylamine (5) and aniline (6) were performed in the presence of trimethylamine in THF.Five novel cyclopropanemethylamino- and anilino-substituted spiro-2,2′-dioxybiphenyl cyclotriphosphazene derivatives(7–11) were obtained from these reactions.
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Key Findings & Data:The molecular structures of the new cyclotriphosphazene derivatives (7–11) were characterized by elemental analysis, MALDI-TOF MS, FT-IR, and NMR ( 31P and 1 H) spectroscopies.
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Conclusion & Impact:Thestructure of the spiro-(2,2′-dioxybiphenyl)-bis-(anilino)-cyclotriphosphazene (11) was also determined by single-crystalX-ray crystallography.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters

Abstract

The nucleophilic substitution reactions of mono- and bis-spiro-2,2′-dioxybiphenyl cyclotriphosphazenes (3and 4) with cyclopropanemethylamine (5) and aniline (6) were performed in the presence of trimethylamine in THF.Five novel cyclopropanemethylamino- and anilino-substituted spiro-2,2′-dioxybiphenyl cyclotriphosphazene derivatives(7–11) were obtained from these reactions. The molecular structures of the new cyclotriphosphazene derivatives (7–11) were characterized by elemental analysis, MALDI-TOF MS, FT-IR, and NMR ( 31P and 1 H) spectroscopies. Thestructure of the spiro-(2,2′-dioxybiphenyl)-bis-(anilino)-cyclotriphosphazene (11) was also determined by single-crystalX-ray crystallography.

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Cite This Article

ÇİFTÇİ, G. Y., EÇİK, E. T., ERDEMİR, E., İBİŞOĞLU, H., DEMİR, G., YÜKSEL, F. (2022). Nucleophilic substitution reactions of monofunctional nucleophilic reagents with cyclotriphosphazenes containing 2,2-dioxybiphenyl units. Turkish Journal of Chemistry, Cilt: 44 - Sayı: 1, 87–98. https://ajindex.com/articles/601559

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References (13)

  1. Mukundam V, Dhanunjayarao K, Mamidala R, Venkatasubbaiah K. Synthesis, characterization and aggregation induced enhanced emission properties of tetraaryl pyrazole decorated cyclophosphazenes. Journal of Materials Chemistry C 2016; 4 (16): 3523-3530
  2. Caminade AM, Hameau A, Majoral JP. The specific functionalization of cyclotriphosphazene for the synthesis of smart dendrimers. Dalton Transactions 2016; 45 (5): 1810-1822
  3. Wang L, Yang YX, Shi X, Mignani S, Caminade AM et al. Cyclotriphosphazene core-based dendrimers for biomedical applications: an update on recent advances. Journal of Materials Chemistry B 2018; 6 (6): 884-895
  4. Januszewski R, Dutkiewicz M, Orwat B, Maciejewski H, Marciniec B. A library of multisubstituted cyclotriphosphazenes molecular scaffolds for hybrid materials. New Journal of Chemistry 2018; 42 (19): 15552-15555
  5. Tanrıverdi-Eçik E, Şenkuytu E, Cebesoy Z, Çiftçi GY BODIPY decorated dendrimeric cyclotriphosphazene photosensitizers: synthesis and efficient singlet oxygen generators. RSC Advances 2016; 6 (53): 47600-47606
  6. Şenkuytu E, Tanrıverdi-Eçik E, Durmuş M, Çiftçi GY. Monofunctional amines substituted fluorenylidene bridged cyclotriphosphazenes: ‘Turn-off’ fluorescence chemosensors for Cu 2+ and Fe 3+ ions. Polyhedron 2015; 101: 223- 229
  7. Chandrasekhar V, Narayanan RS. Metalation studies of 3- and 4-pyridyloxycyclophosphazenes: Metallamacrocycles to coordination polymers. Dalton Transactions 2013; 42 (18): 6619-6632
  8. Bilge S, Demiriz Ş, Okumuş A, Kılıç Z, Tercan B et al. Phosphorus−Nitrogen Compounds. Part 13. Syntheses, crystal structures, spectroscopic, stereogenic, and anisochronic properties of novel spiro-ansa-spiro-, spiro-binospiro-, and spiro-crypta phosphazene derivatives. Inorganic Chemistry 2006; 45 (21): 8755-8767
  9. Okutan E, Çoşut B, Yeşilot S. Synthesis and properties of fullerene (C60) substituted cyclophosphazene derivatives. Inorganic Chemistry Communications 2014; 49: 1-4
  10. Allen CW. Regio-and stereochemical control in substitution reactions of cyclophosphazenes. Chemical Reviews 1991; 91 (2): 119-135
  11. Chandrasekhar V, Thilagar P, Pandian M. Cyclophosphazene-based multi-site coordination ligands. Coordination Chemistry Reviews 2007; 251: 1045-1074
  12. Benson MA, Ledger J, Steiner A. Zwitterionic phosphazenium phosphazenate ligands. Chemical Communications 2007; 3823-3825
  13. Ibisoglu H, Besli S, Yuksel F, Un I, Kılıç A. Investigation of nucleophilic substitution pathway for the reac