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159-66-0

159-66-0 Structure

159-66-0 Structure
IdentificationMore
[Name]

9,9'-Spirobi[9H-fluorene]
[CAS]

159-66-0
[Synonyms]

9,9'-spirobi[9h-fluorene]
9,9'-SPIROBIFLUORENE
9,9'-Spirobi[9H-fluorene]9,9'-Spirobi[9H-fluorene]
[Molecular Formula]

C25H16
[MDL Number]

MFCD08704216
[Molecular Weight]

316.39
[MOL File]

159-66-0.mol
Chemical PropertiesBack Directory
[Melting point ]

202 °C
[Boiling point ]

474.9±40.0 °C(Predicted)
[density ]

1.28±0.1 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,Room Temperature
[form ]

Solid
[color ]

White to pale yellow
[Water Solubility ]

Soluble in common organic solvents. Slightly soluble in water.
[InChIKey]

SNFCXVRWFNAHQX-UHFFFAOYSA-N
[CAS DataBase Reference]

159-66-0(CAS DataBase Reference)
Safety DataBack Directory
[Safety Statements ]

24/25
[WGK Germany ]

3
[HS Code ]

29029090
Hazard InformationBack Directory
[Chemical Properties]

white powder
[Uses]

A blue light emitting material in organic light emitting diodes (OLEDs). Also used as a blue-emitting material in electroluminescent devices.
[General Description]

9,9′-Spirobifluorene is a polyfluorene with carbon atoms of the methylene bridge connected to two fluorene molecules. It is mainly used in organic electronics due to its robust structure and two perpendicularly arranged π systems.
[Synthesis]

9-(2-Biphenylyl)fluoren-9-ol

67665-44-5

9,9'-Spirobi[9H-fluorene]

159-66-0

GENERAL PROCEDURE: 9-(2-Biphenylyl)-9-fluorenol (130 mg, 0.5 mmol) was placed in a 5 mL round-bottomed flask and 1 mL of dry nitromethane was added as solvent. Anhydrous FeCl3 (5 mg, 0.025 mmol) was then added and the reaction mixture was stirred at room temperature for 5 min. Upon completion of the reaction, the solvent was removed by vacuum evaporation and the residue was purified by silica gel column chromatography using petroleum ether (boiling point 60-80 °C) as eluent to afford the target product 9,9-spirobifluorene (116 mg, 0.48 mmol, 96% yield) as a white solid with a melting point of 132 °C. 1H NMR (CDCl3, 300 MHz) δ 5.08 (s , 1H), 7.11-7.12 (m, 2H), 7.25-7.36 (m, 7H), 7.42 (t, J = 7.29 Hz, 2H), 7.84 (d, J = 7.6 Hz, 2H) ppm.13C NMR (CDCl3, 75 MHz) δ 54.4, 119.8, 125.3, 126.8, 127.3, 128.3, 128.7, 141.0, 141.6, 147.8 ppm.

[References]

[1] Journal of Materials Chemistry A, 2016, vol. 4, # 22, p. 8750 - 8754
[2] Journal of Organic Chemistry, 1996, vol. 61, # 20, p. 6906 - 6921
[3] Journal of the American Chemical Society, 1990, vol. 112, # 14, p. 5662 - 5663
[4] European Journal of Organic Chemistry, 2010, # 21, p. 4004 - 4016
[5] Tetrahedron Letters, 2012, vol. 53, # 41, p. 5544 - 5547
Spectrum DetailBack Directory
[Spectrum Detail]

9,9'-Spirobi[9H-fluorene](159-66-0)1HNMR
Well-known Reagent Company Product InformationBack Directory
[TCI AMERICA]

9,9'-Spirobi[9H-fluorene],>98.0%(LC)(159-66-0)
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