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

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 Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29029090

9,9'-Spirobi[9H-fluorene] Usage And Synthesis

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.

Uses

9,9′-Spirobifluorene can be used in the synthesis of spirobifluorene based conjugated microporous polymers which can be potentially be used as a gas absorbent. It may be used as a hole transporting material which can be used in the fabrication of perovskite solar cells.

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

9,9'-Spirobi[9H-fluorene](159-66-0)Related Product Information

• 9,9'-Spirobi[9H-fluorene]-2-boronic Acid
• 9,9-Dioctyl-2,7-dibromofluorene
• 2-Amino-9,9-dimethylfluorene
• 9,9'-Spirobi[9H-fluorene]-4-ylboronicacid
• 2-Amino-9,9-diphenylfluorene
• 9,9-Diphenylfluorene
• 9,9-Dimethyl-9H-fluoren-2-yl-boronic acid
• 9,9-Dihexyl-9H-fluoren-2-boronic acid
• 9,9-DIMETHYL-9,10-DIHYDRO-ACRIDINE
• 9,9-Dimethyl-9H-fluorene
• Fluorene
• 2,2',7,7'-Tetrabromo-9,9'-spirobifluorene
• 2,2',7,7'-Tetrakis(diphenylamino)-9,9'-spirobifluorene
• 2,2'-DIBROMO-9,9'-SPIROBIFLUORENE
• 2,7-Dibromo-9,9'-spiro-bifluorene
• 2-Bromo-9,9'-spirobi[9H-fluorene]
• 9,9'-SPIROBI[9H-FLUORENE]-3,6-DIAMINE, N3,N3,N6,N6-TETRAPHENYL-
• N,N'-Bis(3-methylphenyl)-N,N'-diphenyl-9,9-spirobifluorene-2,7-diamine