| Identification | More | [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 Properties | Back 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. | [InChI]
1S/C25H16/c1-5-13-21-17(9-1)18-10-2-6-14-22(18)25(21)23-15-7-3-11-19(23)20-12-4-8-16-24(20)25/h1-16H | [InChIKey]
SNFCXVRWFNAHQX-UHFFFAOYSA-N | [SMILES]
c1ccc2c(c1)-c3ccccc3C24c5ccccc5-c6ccccc46 | [CAS DataBase Reference]
159-66-0(CAS DataBase Reference) |
| Hazard Information | Back 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]
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 |
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