2,4,6-tris[3-(diphenylphosphinyl)phenyl]-1,3,5-triazine
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Product Description
2,4,6-Tris(3-(diphenylphosphinyl)phenyl)-1,3,5-triazine, commonly known as PO-T2T, is a sophisticated organic compound. This highly π-conjugated molecule features a central 1,3,5-triazine core adorned with three 3-phenyl units, each bearing a diphenylphosphinyl group in the meta position. Its electron-deficient nature, stemming from the triazine core, makes it an ideal material for electron transport layers (ETL) and hole blocking layers (HBL) in organic light-emitting diodes (OLEDs). PO-T2T is particularly valued for its role in exciplex formation, which is crucial for advancing Thermally Activated Delayed Fluorescence (TADF) OLEDs. Spectroscopically, it exhibits a complex aromatic region in ¹H NMR, a downfield phosphine-oxide signal in ³¹P NMR, and strong P=O stretches in IR.
Synthesis Methods
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Formation of Central Core: Cyanuric chloride (2,4,6-trichloro-1,3,5-triazine) is used as the starting material.
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Nucleophilic Aromatic Substitution: Chlorine atoms are displaced by a nucleophile (e.g., Grignard reagent or aryl boronic acid) derived from a diphenylphosphine precursor.
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Oxidation: Phosphorus atoms are oxidized from trivalent (P³⁺) to pentavalent (P⁵⁺) state using agents like hydrogen peroxide (H₂O₂) or meta-chloroperoxybenzoic acid (mCPBA).
Uses
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Primary Application: OLEDs (Organic Light-Emitting Diodes)
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Role: Ancillary ligand in phosphorescent OLEDs, particularly for red and green light emission.
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Mechanism: Coordinates with lanthanide ions (e.g., Eu³⁺, Tb³⁺) to form stable complexes, shielding them from non-radiative decay pathways and acting as an "antenna" to transfer energy to the central ion.
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Benefits: High efficiency and stability in OLED devices.
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Other Applications:
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Electron transport layer (ETL) and hole blocking layer (HBL) in OLEDs.
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Exciplex formation in Thermally Activated Delayed Fluorescence (TADF) OLEDs.
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Interface modification in perovskite light-emitting diodes (Pero-LEDs) to enhance charge injection and device performance.
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Molecular Formula and Composition
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Molecular Formula: C₅₇H₄₂N₃O₃P₃
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Average Molar Mass: 909.8989 g/mol
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Monoisotopic Mass: 909.243903 u
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Elemental Mass Percent:
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Carbon (C): 75.24%
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Hydrogen (H): 4.65%
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Nitrogen (N): 4.62%
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Oxygen (O): 5.27%
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Phosphorus (P): 10.21%
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Structure and Functional Notes
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Core: 1,3,5-triazine ring with three identical aryl substituents at the 2,4,6 positions.
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Substituents: Each substituent is a 3-phenyl unit carrying a diphenylphosphinyl group (P=O with two phenyls attached) in the meta position on the phenyl ring.
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Functional Groups:
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Triazine core: Electron-deficient, contributing to its role in electron transport layers.
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Phosphine oxide groups (P=O): High dipole moment, excellent Lewis base, and strong affinity for Lewis acids, particularly lanthanide ions.
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Physical Properties
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Appearance: White or off-white crystalline powder.
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Solubility: Soluble in common organic solvents (CHCl₃, DCM, toluene, THF, DMF) and insoluble in water.
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Symmetry: High C₃ symmetry.
Spectroscopic Properties
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¹H NMR (CDCl₃): Complex aromatic region with multiple multiplets between ~7.0–8.8 ppm; no aliphatic protons.
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³¹P NMR (CDCl₃): Phosphine-oxide P signal typically appears downfield (≈ +20 to +40 ppm).
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IR: Strong P=O stretch around ~1150–1250 cm⁻¹; aromatic C–H stretches at 3000–3100 cm⁻¹.
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UV–Vis: Strong π→π* absorption in the UV, possibly extending into the visible region.
Handling and Safety
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Handling: Treat as an organic laboratory chemical; use gloves, eye protection, and work in a fume hood. Avoid inhalation of dust and keep away from strong reducing agents.
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Disposal: Dispose of according to institutional or municipal regulations.
Analytical Tips
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Identity Verification: HRMS (m/z ≈ 910.2517 for [M+H]⁺), ¹H NMR, and ³¹P NMR.
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Elemental Analysis: Should match the percent composition within experimental error.