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Product Details
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Description |
2-Bromo-9, 9’-spirobifluorene is a derivative of 9,9'-spirobifluorene. It is a quite useful blue light emitting material used in the organic light emitting diodes (OLEDs). It possesses high photoluminescence efficiency and good chemical stability. Moreover, It has high glass-transition temperature, excellent thermal stability and easy color tenability through introducing low band gap co-monomers. |
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Chemical Properties |
Off-white to light yellow crystal or powder |
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Synthesis |
Synthesis of 2-bromo-spirofluorene2-bromo-9-hydroxy-9-(2-biphenyl)fluorene (2g) dissolved in 25 mL acetic acid (15 mol/L) containing hydrochloric acid (12 mol/L) was refluxed for about 2 h to separate out a white solid, which was recrystallized with ethanol to produce white crystals of 2-bromo-spirofluorene (1.2 g, yield 63%). GC-MS (m/z +): 394. 1HNMR (400 MHz, CDCl3, ppm):δ7.80～7.86 (m, 3H), δ7. 70 (d, 1H),δ7.48 (m, 1H), δ7.36 ～ 7.40 (m, 3H), δ7.13 (m, 3H), δ6.84 (d, 1H), δ6.72 (m, 3H) |
N-Substitution in perylene diimide (PDI)...
A high efficient UV-violet emission type...
As we know, 2-bromo-9,9′-spirobifluorene can be readily synthesized from 2-bromo-9-… (7) However, this method is unsuitable for the synthesis of 4-bromo-9,9′-spirobifluorene …
2-bromofluoren-9-one
2-bromo-9,9'-spirobifluorene
| Conditions | Yield |
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2-bromofluoren-9-one; With n-butyllithium; 2-Bromobiphenyl; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere; Schlenk technique;
With hydrogenchloride; acetic acid; In water; at 70 ℃; for 2h;
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67% |
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With biphenyl-2-yl-lithium; Multistep reaction;
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Multi-step reaction with 2 steps
1: diethyl ether / 3 h / Heating
2: conc. H2SO4 / 3 h
With sulfuric acid; In diethyl ether; 1: Grignard reaction / 2: Friedel-Crafts reaction;
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Multi-step reaction with 2 steps
1.1: Mg / diethyl ether / Heating
1.2: diethyl ether / Heating
2.1: 10.4 g / conc. HCl / acetic acid / Heating
With hydrogenchloride; magnesium; In diethyl ether; acetic acid; 1.2: Grignard reaction;
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Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran / -78 °C
1.2: 3 h / 20 °C
2.1: acetic acid / sulfuric acid / 1 h / Heating
With n-butyllithium; acetic acid; sulfuric acid; In tetrahydrofuran;
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Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C
1.2: -78 - 20 °C
2.1: hydrogenchloride; acetic acid / water / 1 h / Reflux
With hydrogenchloride; n-butyllithium; acetic acid; In tetrahydrofuran; water;
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Multi-step reaction with 2 steps
1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C
2: acetic acid; hydrogenchloride / water / 1 h / Reflux
With hydrogenchloride; n-butyllithium; acetic acid; In tetrahydrofuran; water;
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9-(biphenyl-2-yl)-2-bromo-9-fluorenol
2-bromo-9,9'-spirobifluorene
| Conditions | Yield |
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With acetic acid; sulfuric acid; for 1h; Heating;
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97% |
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With acetic acid; at 100 ℃; for 12h; Inert atmosphere;
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91% |
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With hydrogenchloride; acetic acid; In water; for 1h; Reflux;
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85% |
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With hydrogenchloride; acetic acid; In water; for 1h; Reflux;
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81% |
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With hydrogenchloride; acetic acid; for 0.5h; Heating / reflux;
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79% |
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With hydrogenchloride; In water; acetic acid; for 2h; Heating / reflux;
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57% |
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With hydrogenchloride; acetic acid; In water; for 2h; Heating / reflux;
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57% |
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With hydrogenchloride; acetic acid; for 2h; Heating / reflux;
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57% |
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With hydrogenchloride; acetic acid; at 120 ℃; for 2h;
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57% |
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With hydrogenchloride; acetic acid; for 2h; Heating / reflux;
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57% |
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With acetic acid; for 2h; Reflux; Acidic conditions;
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57% |
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With sulfuric acid; for 3h;
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With hydrogenchloride; In acetic acid; Heating;
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10.4 g |
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With acetic acid; hydrogenchloride; at 100 ℃; for 1.5h;
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With hydrogenchloride; In acetic acid;
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With hydrogenchloride; acetic acid; In water; for 12h; Reflux;
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11.3 g |
2-bromofluoren-9-one
2-iodobiphenyl
9-(biphenyl-2-yl)-2-bromo-9-fluorenol
2-biphenylmagnesium bromide
2′-cyano-9,9-spirobifluorene
9,9'-spirobi[9H-fluoren]-2'-yl-boronic acid
2-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-spiro-9,9'-bifluorene
C68H41N
CAS:28320-31-2
Molecular Formula:C<sub>15</sub>H<sub>13</sub>Br
Molecular Weight:273.17
CAS:171408-84-7
Molecular Formula:C25H14Br2
Molecular Weight:474.2
