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

white powder

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.

General procedure: Compound 1a (130 mg, 0.5 mmol) was taken in a 5 mL round bottom flask containing 1 mL of dry nitromethane solvent. Anhydrous FeClTo 130 g of a toluene solution of 9- (2-biphenyl) -9-fluorene alcohol obtained in Example 1, 9.5 g (0.095 mol, 1.00 M.R.) of concentrated sulfuric acid was charged, The reaction was carried out at room temperature for 2 hours.After washing the resulting reaction mixture with caustic water, The organic layer containing the reaction mixture was washed with water until the washing water became neutral.After washing with water, After concentrating the organic layer to an appropriate place, 255 g of methanol was added thereto for crystallization, followed by filtration and drying, 24.0 g of white crystals of 9, 9'-spirobifluorene (yield: 84percent, total yield from Example 1, purity 98percent) were obtained.Under the protection of argon, 10 mmol of 9-fluorenone was added to the reaction flask.11mmol of 2-fluorobiphenyl and 20ml of tetrahydrofuran solvent, after stirring evenly, 22 mmol of lithium metal tablets were added to the reaction solution in batches.Then, the temperature is raised to about 70 ° C, and the reaction is carried out for 6 hours. After the reaction is completed and returned to room temperature, The reaction was quenched with 20 mL of 1N aqueous hydrochloric acid. Dissolve to obtain an organic phase, The tetrahydrofuran was evaporated to dryness on a rotary evaporator to give a solid.The crude solid was added to 10 ml of acetic acid and heated to 80 ° C for 6 hours.After the completion of the ring closure reaction, the crude 9, 9'-spirobifluorene was obtained by filtration.The crude product uses a mixed solvent of dichloromethane and n-hexane as an eluent.Perform column chromatography separation, and the chromatographic silica gel is 200-300 mesh.Finally, the product 9, 9'-spirobifluorene 2.59g is obtained.The yield was 82percent.The dried 9-(2-biphenyl)-9-fluorenol was then dissolved in 500 ml of hot glacial acetic acid. 0.5 ml of concentrated HCl was added to this solution. The solution was boiled for a few minutes and the 9, 9'-Spirobifluorene was prepared using the procedure of Clarkson and Gomberg as follows. To a solution of 9-(2-biphenyl)-9-fluorenol (11.8 g, 35.3 mmol) in refluxing acetic acid was added concentrated hydrochloric acid (0.1 mL) and the solution heated to reflux for 20 min. The solution was cooled to room temperature, and water (50 mL) was added. The resulting white solid was filtered and washed with water and dried in vacuo. No further purification was required to afford 10.9 g. (98%) of the desired compound as a white solid. IR (KBr) 3038.2, 3011.0, 1654.2, 1560.1, 1447.6, 749.3 cm-1. 1 H NMR (500 MHz, CDCl3)delta 7.82 (d, J=7.7 Hz, 4H), 7.34 (t, J=7.5 Hz, 4H), 7.08 (t, J=7.5 Hz, 4H), 6.71 (d, J=7.6 Hz, 4H).

Pharmaceutical intermediates are also important intermediates for the synthesis of optoelectronic materials

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

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.

Molecular Weight:316.4
XLogP3:6.4
Exact Mass:316.125200510
Monoisotopic Mass:316.125200510
Heavy Atom Count:25
Complexity:413
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes