Synthesis and characterization of new (dimethylsilyl)phenoxy and (dimethyl(vinyl)silyl)phenoxy substituted cyclotriphosphazenes

Januszewski, Rafał; Dutkiewicz, Michał; Kubicki, Maciej; Dutkiewicz, Grzegorz; Maciejewski, Hieronim; Marciniec, Bogdan

doi:10.1016/j.jorganchem.2017.10.030

Cited by 16 publications

(6 citation statements)

References 30 publications

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“…Consequently, an up‐field shift in a few 1 H and 13 C signals is observed for CP‐( R ), and CP‐( S ) compared to free BINOLs. The 31 P NMR peak of hexachlorocyclotriphosphazene (20.24 ppm) shows a downfield shift (27.24 for CP‐( R ), and 27.34 for CP‐( S )) after coordinating with the CP ring [22] …”

Section: Resultsmentioning

confidence: 99%

“…The 31 P NMR peak of hexachlorocyclotriphosphazene (20.24 ppm) shows a downfield shift (27.24 for CP-(R), and 27.34 for CP-(S)) after coordinating with the CP ring. [22] In 1998 Carriedo et al reported the synthesis and specific rotations of CP-(R), and CP-(S) along with few other phospha-zene derivatives. [23] In 2004, Kumara Swamy and co-workers synthesized several unsymmetrical bis-and tris-spirocyclic cyclotriphosphazene compounds including CP-(R), and CP-(S) containing 1,1'-bi-2-naphthoxy residue.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

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Single Molecular Persistent Room‐Temperature Phosphorescence and Circularly Polarized Luminescence from Binaphthol‐Decorated Optically Innocent Cyclotriphosphazenes

Jena,

Thayyil Muhammed Munthasir,

Pradhan

et al. 2023

Chemistry A European J

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Circularly polarized luminescence (CPL) features of BINOL‐decorated cyclotriphosphazenes are reported for the very first time. The luminescence dissymmetry factor (glum) of these compounds in chloroform solutions and 1 % polymethyl methacrylate (PMMA) matrix are found to be 1.0 x 10‐3, and 2.9 x 10‐3, respectively. However, no CPL signal is observed for the pristine solids. The enantiomers (R/S) show ultraviolet photoluminescence (~ 350‐360 nm) in solution and solid state. These compounds show ~ 10 times larger absolute photoluminescence quantum yield (PLQY) than the simple BINOLs in the solutions state. In solid‐state, cyclophosphazene‐(R) shows larger PLQY than binaphthol‐(R); in contrast, (S)‐enantiomer shows lower PLQY than binaphthol‐(S), which indicates that the isomer‐dependent solid‐state packing of these compounds plays a crucial role in controlling the PL. Thin films with more than 1 % doping concentration and pristine solids of these compounds do not show persistent room temperature phosphorescence (pRTP) due to concentration‐caused quenching. However, thin films (1 % PMMA) of these chiral emitters exhibit pRTP characteristics with a lifetime of ~ 159‐343 ms under vacuum. Detailed theoretical calculations reveal that the cyclophosphazene acts as an optically innocent dendritic core, and the optical features of these compounds are dictated by the pendent BINOL chromophore.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis and Characterizationmentioning

confidence: 99%

Single Molecular Persistent Room‐Temperature Phosphorescence and Circularly Polarized Luminescence from Binaphthol‐Decorated Optically Innocent Cyclotriphosphazenes

Jena,

Thayyil Muhammed Munthasir,

Pradhan

et al. 2023

Chemistry A European J

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“…Cyclophosphazene derivatives have been widely studied for their flame retardancy and reactivity in the field of flame retardants. Phosphazene compounds obtained by nucleophilic substitution reaction with hexachlorocyclotriphosphazene are a class of compounds containing P = N in the molecule structure [97,98]. Due to the synergistic flame retardance of phosphorus and nitrogen, the addition of cyclotriphosphazene to EP could significantly improve the thermal and flame retardancy properties of EP, further improving the safety of EP in various application fields.…”

Section: Phosphorus/nitrogen Synergistic Flame Retardantmentioning

confidence: 99%

Recent Developments in the Flame-Retardant System of Epoxy Resin

et al. 2020

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With the increasing emphasis on environmental protection, the development of flame retardants for epoxy resin (EP) has tended to be non-toxic, efficient, multifunctional and systematic. Currently reported flame retardants have been capable of providing flame retardancy, heat resistance and thermal stability to EP. However, many aspects still need to be further improved. This paper reviews the development of EPs in halogen-free flame retardants, focusing on phosphorus flame retardants, carbon-based materials, silicon flame retardants, inorganic nanofillers, and metal-containing compounds. These flame retardants can be used on their own or in combination to achieve the desired results. The effects of these flame retardants on the thermal stability and flame retardancy of EPs were discussed. Despite the great progress on flame retardants for EP in recent years, further improvement of EP is needed to obtain numerous eco-friendly high-performance materials.

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“…The choice of reagent is of particular importance in the design of molecules. If the reagent is an alcohol, the reaction follows the nongeminal reaction pathway in cyclophosphazene chemistry, [29][30][31][32] and the nongeminal cis products are predominantly formed when aliphatic chain alcohols are used. [33][34][35][36] In this work, carbazole and 2-methylindole compounds were first modified from the N-side so that starting reagents (I and II) include an ethyl alcohol chain.…”

Section: Introductionmentioning

confidence: 99%

Designing inorganic–organic hybrid molecules based on carbazole/indole-appended cyclotriphosphazenes and the investigation of their photophysical properties

Palabıyık¹,

Balcı²,

Tümay³

et al. 2023

New J. Chem.

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Synthesis and characterization of new (dimethylsilyl)phenoxy and (dimethyl(vinyl)silyl)phenoxy substituted cyclotriphosphazenes

Cited by 16 publications

References 30 publications

Single Molecular Persistent Room‐Temperature Phosphorescence and Circularly Polarized Luminescence from Binaphthol‐Decorated Optically Innocent Cyclotriphosphazenes

Single Molecular Persistent Room‐Temperature Phosphorescence and Circularly Polarized Luminescence from Binaphthol‐Decorated Optically Innocent Cyclotriphosphazenes

Recent Developments in the Flame-Retardant System of Epoxy Resin

Designing inorganic–organic hybrid molecules based on carbazole/indole-appended cyclotriphosphazenes and the investigation of their photophysical properties

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