Diamine compound containing symmetrical double-fluorophore structure, preparation and application of diamine compound, polyamide and polyimide, and preparation and application of polyamide and polyimide
A fluorescent compound and dual fluorophore technology, applied in the field of electronically controlled fluorescence, can solve the problems of long transition time, high oxidation potential, and low fluorescence contrast, and achieve the effects of enhanced dissolution and film formation, enhanced fluorescence intensity, and high fluorescence contrast
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[0029] The present invention provides a preparation method of a diamine compound containing a symmetrical double fluorophore structure described in the above technical scheme, comprising the following steps:
[0030] Mixing p-phenylenediamine, p-fluoronitrobenzene, the first catalyst and an organic solvent to perform a substitution reaction to obtain a dinitro monomer;
[0031] Mixing the dinitro monomer, the brominated fluorescent compound, the second catalyst and a polar solvent, and performing a coupling reaction to obtain a dinitro compound;
[0032] Mixing the dinitro compound, the third catalyst, a reducing agent and a mixed solvent, and performing a reduction reaction to obtain a diamine compound containing a symmetrical double fluorophore structure having a structure shown in formula I;
[0033] The dinitro monomer has a structure shown in formula II-1:
[0034]
[0035] The structural formula of the brominated fluorescent compound is Br-R;
[0036] The dinitro co...
Embodiment 1
[0101] Preparation of monomer N,N'bis(4-nitrophenyl)-1,4-p-phenylenediamine, its structure is:
[0102]
[0103] Under nitrogen, add 21.6g (200mmol) of p-phenylenediamine, 64.9g (460mmol) of p-fluoronitrobenzene, 101.2g (1000mmol) Triethylamine and 45.1g (140mmol) tetrabutylammonium bromide, and then add 424mL sulfolane, the solid content of the resulting system is 30.3wt%, reacted at 180°C under microwave conditions for 7h, cooled the resulting product system to room temperature and discharged Suction filtration and drying in 2000mL ice water to obtain a reddish-brown crude material, which was recrystallized three times with a DMSO / ethanol solution with a volume ratio of 1:3 to obtain 29.4 g of purple-red N,N'-bis(4- Nitrophenyl)-1,4-p-phenylenediamine powder, the yield is 42%. 1 H NMR (300 MHz, DMSO-d 6 )δ9.29(s,1H),8.14–8.03(d,2H),7.27(s,2H),7.09–6.97(d,2H).
[0104] The preparation of diamine monomer N,N'-bis(4-aminophenyl)-N,-bis(naphthyl)-1,4-p-phenylenediamine, it...
Embodiment 2
[0109] Preparation of diamine monomer N, N'-bis(4-aminophenyl)-N,N'-bis(9,9 spirobifluorenyl)-1,4-p-phenylenediamine, its structure is:
[0110]
[0111] Under a nitrogen atmosphere, add 4.2 g (12 mmol) of N,N'-bis(4-nitrophenyl)-1,4 -p-phenylenediamine, 9.8g (24.8mmol) 2-bromo-9,9' spirobis(9H-fluorene), 3.8g (60mmol) copper powder, 13.2g (96mmol) potassium carbonate and 1.9g (7.2mmol) 18 crown ether-6, then add 50mL o-dichlorobenzene, the solid content of the obtained system is 33.5wt%, react at 160°C for 24h, filter while hot to remove copper powder and salt, distill the filtrate under reduced pressure, and use a volume ratio of 2:1 dichloromethane / petroleum ether was used as a developing solvent for column chromatography to obtain 6.1 g of orange-yellow dinitro compounds with a yield of 52.0%;
[0112] Under nitrogen protection atmosphere, in the 250mL three-neck flask that magnetic stirring bar and condenser tube are housed, add 3.0g (3.1mmol) dinitro compound, in the...
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