Eine neue Synthese und die Kristallstruktur von Hexaphenyl-cyclo-triphosphazen, [NPPh2]3 · THF

Dietrich, Armin; Neumüller, Bernhard; Dehnicke, Kurt

doi:10.1002/1521-3749(200010)626:10<2035::aid-zaac2035>3.0.co;2-v

Cited by 4 publications

(4 citation statements)

References 3 publications

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“…The calculated dihedral angles between the outer phenyl rings and the central ring plane are 48 to 56°. The calculated dihedral angles and bond lengths are consistent with experimental crystallographic data of CP1 . As no conjugation over the central ring takes place, all phenyl rings are electronically isolated from each other.…”

Section: Resultssupporting

confidence: 81%

Phosphazene-Based Host Materials for the Use in Blue Phosphorescent Organic Light-Emitting Diodes

et al. 2011

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We present a series of low-molecular-weight materials based on cyclic phosphazenes for the use as host materials in blue phosphorescent organic light-emitting diodes. Substituted phenyl rings are attached to the central phosphazene ring either via phosphorus–oxygen bonds to yield phenoxy-substituted derivatives or via direct phosphorus–carbon bonds to yield phenyl-substituted derivatives. The phenoxy substituted cyclic phosphazenes were prepared by nucleophilic substitution of the six chlorine atoms in hexachlorocyclotriphosphazene with phenoxy groups, whereas the phenyl substituted cyclic phosphazenes were formed in a cyclocondensation reaction of three equivalents of substituted phosphinic amides. The phenyl substitution leads to materials with superior thermal properties compared to the phenoxy substitution. Because of the nonconjugated linkage to the phosphazene core, the host materials have very high triplet energies of more than 3 eV. In an OLED device using one compound as host for the saturated blue phosphorescent emitter Ir(dbfmi), a peak power efficiency of 7.6 lm W–1 and a peak luminance of 5000 cd m–2 were achieved.

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Section: Resultssupporting

confidence: 81%

Phosphazene-Based Host Materials for the Use in Blue Phosphorescent Organic Light-Emitting Diodes

et al. 2011

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“…The structure of a fourth, related cyclotriphosphazene with six para-fluorophenoxy groups, was reported by other investigators (Wahl et al, 2012) and was independently verified by us. The non-fluorinated hexa(phenoxy)cyclotriphosphazene tetrahydrofuran solvate x-ray structure was also described earlier (Dietrich et al, 2000).…”

Section: Chemical Contextmentioning

confidence: 86%

“…A similar calculation in 2 shows atom P2 displaced by 0.232 (4) Å , and in 3 atom N3 is displaced the least, only by 0.205 (4) Å . In earlier structure reports: [(NPCl 2 ) 3 : Bullen, 1971; (NPF 2 ) 3 : Singh et al, 2000; (NPPh 2 ) 3 ÁTHF: Dietrich et al, 2000], the cyclotriphosphazene ring was always planar, i.e. no puckering was seen.…”

Section: Figurementioning

confidence: 92%

“…However, the structures in the present study, as well as a series of polymorph structures of hexakis(4-fluorophenoxy) cyclotriphosphazene reported by Wahl et al (2016) have no solventaccessible voids. Various cyclotriphosphazene structures have been reported in the literature: [(NPCl 2 ) 3 , CSD refcode KAGKUY: Bullen, 1971; (NPF 2 ) 3 , VARYES02: Singh et al, 2000; (NPPh 2 ) 3 ÁTHF, GUHPII: Dietrich et al, 2000]. For a review of the expanding field of polyphosphazene high polymers, see: Allcock (2016).…”

Section: Database Surveymentioning

confidence: 99%

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Crystal structures of three hexakis(fluoroaryloxy)cyclotriphosphazenes

Yennawar¹,

Hess²,

Allcock³

2019

Acta Cryst E

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The syntheses and crystal structures of three cyclotriphosphazenes, all with fluorinated aryloxy side groups that generate different steric characteristics, viz. hexakis(pentafluorophenoxy)cyclotriphosphazene, N3P3(OC6F5)6, 1, hexakis[4-(trifluoromethyl)phenoxy]cyclotriphosphazene, N3P3[OC6H4(CF3)]6, 2 and hexakis[3,5-bis(trifluoromethyl)phenoxy]cyclotriphosphazene, N3P3[OC6H3(CF3)2]6 3, are reported. Specifically, each phosphorus atom bears either two pentafluorophenoxy, 4-trifluoromethylphenoxy, or 3,5-trifluoromethylphenoxy groups. The central six-membered phosphazene rings display envelope pucker conformations in each case, albeit to varying degrees. The maximum displacement of the `flap atom' from the plane through the other ring atoms [0.308 (5) Å] is seen in 1, in a molecule that is devoid of hydrogen atoms and which exhibits a `wind-swept' look with all the aromatic rings displaced in the same direction. In 3 an intramolecular C—H(aromatic)...F interaction is observed. All the –CF3 groups in 2 and 3 exhibit positional disorder over two rotated orientations in close to statistical ratios. The extended structures of 2 and 3 are consolidated by C—H...F interactions of two kinds: (a) linear chains, and (b) cyclic between molecules related by inversion centers. In both 1 and 3, one of the six substituted phenyl rings has a parallel-displaced aromatic π–π stacking interaction with its respective symmetry mate with slippage values of 2.2 Å in 1 and 1.0 Å in 3. None of the structures reported here have solvent voids that could lead to clathrate formation.

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Supramolecular Structures of Cyclotriphosphazenes

Steiner

2008

Polyphosphazenes for Biomedical Applications

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Eine neue Synthese und die Kristallstruktur von Hexaphenyl-cyclo-triphosphazen, [NPPh2]3 · THF

Cited by 4 publications

References 3 publications

Phosphazene-Based Host Materials for the Use in Blue Phosphorescent Organic Light-Emitting Diodes

Phosphazene-Based Host Materials for the Use in Blue Phosphorescent Organic Light-Emitting Diodes

Crystal structures of three hexakis(fluoroaryloxy)cyclotriphosphazenes

Supramolecular Structures of Cyclotriphosphazenes

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