Phenanthroimidazole luminescent material containing styryl as well as preparation method and application thereof
A phenanthroimidazole and styrene-based technology, which is applied in the field of phenanthroimidazole light-emitting materials and its preparation, can solve the problems of unavailable characteristic functional groups and monitoring, and achieve the effect of easy reaction and simple synthesis method
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Embodiment 1
[0034] Preparation of E-1-(4'-triphenylamino)-2-(4',1"-phenyl-4"-phenyl-phenanthroimidazole)-ethylene
[0035]
[0036] (1) Weigh 0.274g (1mmol) of 4-formyl triphenylamine, 0.1683g (1.5mmol) of potassium tert-butoxide, 10mL of DMF (dimethylformamide), diethyl (4-cyanobenzyl) phosphonate 1mL (1.2mmol) was placed in a 50mL three-necked flask, followed by thin-layer chromatography to the end point, then added deionized water, extracted 3 times with ethyl acetate, combined the organic phases and dried with anhydrous magnesium sulfate for 24 hours, filtered Separated by column chromatography, 0.34 g of yellow powder (compound 1 in the reaction scheme) was obtained with a yield of 93%. 1 H NMR (300MHz, CDCl 3 )δ7.57(dd,J=20.4,8.1Hz,2H),7.39(d,J=8.5Hz,2H),7.35–7.17(m,6H),7.16–7.02(m,8H),6.95(d , J=16.3Hz, 2H). Infrared spectrum such as figure 1As shown in (1-CN), the characteristic absorption position in the spectrum is located at 2225cm -1 , is the characteristic absorption ...
Embodiment 2
[0044] Preparation of E-1-(4'-phenyl-carbazolyl)-2-(4',1"-phenyl-4"-phenyl-phenanthroimidazole)-ethylene
[0045]
[0046] (1) Weigh 1.0851g (4mmol) of 4-(9H-carbazole)benzaldehyde, 0.1683g (1.5mmol) of potassium tert-butoxide, 40mL of dichloromethane, and 4mL of diethyl (4-cyanobenzyl)phosphonate (4.8mmol) in a 100mL three-necked flask, using thin layer chromatography to track the reaction to the end point, add deionized water, extract 3 times with ethyl acetate, combine the organic phases and dry with anhydrous magnesium sulfate for 24 hours, filter and use After separation by column chromatography, 0.8728 g (2.3 mmol) of a light yellow solid was obtained with a yield of 58%. The outer main absorption wavenumber is 3000cm -1 、2225cm -1 、1450cm -1 、1250cm -1 、550cm -1 . 1 H NMR (300MHz, CDCl 3 )δ8.15 (d, J = 7.3Hz, 2H), 7.83–7.50 (m, 8H), 7.43 (d, J = 5.3Hz, 4H), 7.36–7.08 (m, 4H).
[0047] (2) Weigh 0.8 g (2 mmol) of the light yellow solid compound in (1) and 30 m...
Embodiment 3
[0050]
[0051] (1) Weigh 0.274g (1mmol) of 4-formyltriphenylamine, 0.1683g (3mmol) of potassium tert-butoxide, 20mL of dimethyl sulfoxide, 3mL (3.6mmol) of diethyl (4-cyanobenzyl) phosphonate ) in a 50mL three-necked flask, add deionized water after using thin layer chromatography to track the reaction to the end point, use ethyl acetate to extract 3 times, combine the organic phases and dry with anhydrous magnesium sulfate for 24 hours, filter and use column chromatography Separated to obtain 0.31 g of yellow powder with a yield of 90%.
[0052] (2) Weigh 0.3412 g (1 mmol) of the yellow solid product in (1), put 20 mL of toluene in a 50 mL round bottom flask, control the temperature of the reaction system at -20 °C, and add 2.5 mol / L of Diisobutylaluminum hydride 1 mL, reacted for 12 hours, stopped the reaction, adjusted the pH to 1 with 10% hydrochloric acid, filtered, and dried to obtain 0.30 g of a yellow solid (compound 2 in the reaction scheme), with a yield of 80%. ...
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