Organic room-temperature phosphorescent material with multiple stimulation responses and preparation method and application thereof
A multi-stimulus-responsive, room-temperature phosphorescence technology, applied in luminescent materials, chemical instruments and methods, applications, etc., can solve the problems of single application method, commercial application defects, low safety level, etc., to achieve a simple preparation process and promote the commercialization process. , less toxic effect
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Embodiment 1
[0067] Embodiment 1: the synthesis of compound 1:
[0068]
[0069] Weigh phenothiazine (1.99g, 10mmol), bromobenzene (1.73g, 11mmol), potassium tert-butoxide (1.34g, 12mmol), and palladium acetate (0.11g, 0.5mmol) into a 250mL Schlenk tube, nitrogen Tributylphosphine toluene solution (0.5 mL, 0.25 mmol) and 60 mL toluene were added under protection, and stirred and refluxed under N 2 atmosphere for 12 hours. After the reaction, the mixture was extracted with dichloromethane and water, and the organic phase was collected and dried over anhydrous magnesium sulfate. The organic phase of the extract was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography (eluent: petroleum ether / dichloromethane=10:1) to obtain a light yellow solid. The light yellow solid was dissolved in a mixture of acetic acid and dichloromethane (1:2 by volume), and refluxed at 60°C for 24 hours. After the reaction, the mixture was extracted with dichloro...
Embodiment 2
[0070] Embodiment 2: the synthesis of compound 2:
[0071]
[0072] Weigh phenothiazine (1.99g, 10mmol), 2-bromopyridine (1.75g, 11mmol), potassium tert-butoxide (1.34g, 12mmol), and palladium acetate (0.11g, 0.5mmol) into a 250mL Schlenk tube , tributylphosphinetoluene solution (0.5mL, 0.25mmol) and 60mL toluene were added under nitrogen protection, and stirred and refluxed under N2 atmosphere for 12 hours. After the reaction, the mixture was extracted with dichloromethane and water, and the organic phase was collected and dried over anhydrous magnesium sulfate. The organic phase of the extract was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography (eluent: petroleum ether / dichloromethane=3:1) to obtain a light yellow solid. The light yellow solid was dissolved in a mixture of acetic acid and dichloromethane (1:2 by volume), and refluxed at 60°C for 24 hours. After the reaction, the mixture was extracted with dichlorome...
Embodiment 3
[0073] Embodiment 3: the synthesis of compound 3:
[0074]
[0075] The weighed compound 7 (2.19g, 10mmol), elemental sulfur (0.64g, 20mmol), elemental iodine (76mg, 0.3mmol) and dichlorobenzene (6mL) were added to a 200mL schlenk tube equipped with a magneton, And stirred at 160° C. for 4 hours under the protection of nitrogen. Note that hydrogen sulfide gas is generated during the reaction, so the tail gas should be absorbed by saturated aqueous sodium hydroxide solution. After the reaction was complete, the mixture was cooled to room temperature. The mixture was separated by silica gel column chromatography (eluent: petroleum ether / dichloromethane=5:1) to obtain compound 8.
[0076] The synthesis method of compound 3 is the same as that of compound 1. Compound 3 is a white solid. M.p.249-251℃. 1 H NMR (400MHz, CDCl 3 )δ9.22(d, J=8.7Hz, 1H), 8.28(dd, J=8.0, 1.5Hz, 1H), 7.78–7.64(m, 6H), 7.49(t, J=7.5Hz, 1H), 7.43–7.35(m,3H),7.33–7.26(m,1H),6.72(d,J=9.4Hz,1H),6.54(d...
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