fluoren-9-ylidenehydrazine

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 9-fluorenone hydrazone (9.7 g, 0.05 moles) in 1,2-dichloroethane (50 ml) together with 1,1,3,3-tetramethylguanidine (26.4 ml) and iodine (2 ml, 1% w/v solution) was added peracetic acid solution (11.4 ml, 1.27 × 0.05 moles) over 25 minutes at 10° - 15°. The orange solution was stirred for 15 minutes at 15°, washed with water (5 × 250 ml) and made up to 250 ml in a volumetric flask. An aliquot (50 ml) treated with excess acetic acid yielded 193 ml gas corrected to NTP which corresponded to a 86.2% yield of diazoalkane. washed with water (5 × 250 ml) made up to 250 ml in a volumetric flask An aliquot (50 ml) treated with excess acetic acid

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Unsymmetrical charge transport materials can be prepared by using an unsymmetrical linking compound such as 6-dimethyl-1, 4-benzoquinone. Alternatively, unsymmetrical charge transport materials can be prepared by the following procedure. In the first step, a first 9-fluorenone or a derivative thereof reacts with an excess of hydrazine at 50-70° C. for 1-6 hours to produce a first 9-fluorenone hydrazone compound or a derivative thereof. Then, the first 9-fluorenone hydrazone compound can be isolated and purified. In a subsequent step, a second 9-fluorenone derivative reacts with an excess of hydrazine at 50-70° C. for 1-6 hours to produce a second 9-fluorenone hydrazone derivative. Then, the second 9-fluorenone hydrazone derivative can be isolated and purified. In another step, the first 9-fluorenone hydrazone derivative reacts with a linking compound having 2 aldehyde groups or ketone groups, such as OCH—CHO, a quinone derivative, or a diphenoquinone derivative, in a mole ratio of 1:1 to form an 9-fluorenone azine compound having one aldehyde or ketone group. In the next step, the second 9-fluorenone hydrazone derivative reacts with the 9-fluorenone azine compound in a mole ratio of 1:1 to form the desired product. The desired product can be isolated and purified by recrystalization or/and column chromatography. A person or ordinary skill in the art can reduce the amount of symmetrical by-products, and these symmetrical by-product compounds can be separated in the purification steps. Unsymmetrical charge transport materials can be prepared Alternatively, unsymmetrical charge transport materials can be prepared by the following procedure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Symmetrical charge transport materials can be prepared by the following procedure. In the first step a 9-fluorenone or a derivative compound reacts with an excess of hydrazine at 50-70° C. for 1-6 hours to produce a 9-fluorenone hydrazone compound or derivative thereof. Then, the 9-fluorenone hydrazone compound can be isolated and purified. In the next step, the 9-fluorenone hydrazone reacts with a linking compound having 2 aldehyde groups or ketone groups, such as OCH—CHO, a quinone derivative, or a diphenoquinone derivative, in a mole ratio of 2:1 (2 mole of hydrazine derivative with 1 mole of the linking compound). The desired product can be isolated and purified by recrystalization or/and column chromatography. Symmetrical charge transport materials can be prepared by the following procedure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 9-Fluorenone (200 g, 1.1 mol, from Aldrich, Milwaukee, Wis.) and hydrazine monohydrate (160 ml, 3.3 mol, from Aldrich, Milwaukee, Wis.) were dissolved in 1000 ml of 2-propanol in a 2000 ml 2-neck round bottom flask equipped with a reflux condenser and a mechanical stirrer. Concentrated hydrochloric acid (4 ml) was then added, and the mixture was refluxed for one hour. The mixture was cooled slowly to room temperature, and the crude solid product was harvested by filtration. The solid was washed with isopropanol and then recrystallized from dioxane to obtain 150 g (74% yield) of 9-fluorenone hydrazone. equipped with a reflux condenser and a mechanical stirrer the mixture was refluxed for one hour the crude solid product was harvested by filtration The solid was washed with isopropanol recrystallized from dioxane