A kind of stellate tetraamine pyrene compound, preparation method and application thereof
A star-shaped tetraaminepyrene and compound technology, applied in the field of thermochromic luminescent materials, can solve the problems of low quantum yield and achieve high quantum yield, good accuracy and high sensitivity
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[0038] The invention provides a method for preparing a stellate tetraamine pyrene compound, comprising the following steps:
[0039] Step 1: Preparation of (4'-(bis(4-methoxyphenyl)amino)-(1,1'-biphenyl)-4-yl)boronic acid;
[0040] Under an inert atmosphere, 4'-bromo-N,N-bis(4-methoxyphenyl)-(1,1'-biphenyl)-4-amine undergoes halogen- Lithium exchange reaction forms aryl lithium, aryl lithium and borate undergo nucleophilic substitution reaction to form aryl borate, which is further acidified and hydrolyzed with hydrochloric acid to obtain (4'-(bis(4-methoxy phenyl)amino)-(1,1'-biphenyl)-4-yl)boronic acid. For the reaction equation, see the following reaction equation (1-1).
[0041]
[0042]Among them, 4'-bromo-N,N-bis(4-methoxyphenyl)-(1,1'-biphenyl)-4-amine can be prepared according to existing methods, see the methods recorded in the literature : Y.J.Chang, T.J.Chow. Triaryl linked donor acceptordyads for high-performance dye-sensitized solar cells[J].Tetrahedron 2009...
Embodiment 1
[0060] This embodiment provides a method for preparing a stellate tetraamine pyrene compound, comprising the following steps:
[0061] (1) Preparation of 4'-bromo-N,N-bis(4-methoxyphenyl)-(1,1'-biphenyl)-4-amine;
[0062] The synthesis of 4'-bromo-N,N-bis(4-methoxyphenyl)-(1,1'-biphenyl)-4-amine refers to the reaction formula (1-3), and the synthesis method refers to the literature Y.J. Chang,T.J.Chow.Triaryl linked donor acceptor dyads for high-performance dye-sensitized solar cells[J].Tetrahedron 2009,65:9626–9632.
[0063]
[0064] (2) Preparation of (4'-(bis(4-methoxyphenyl)amino)-(1,1'-biphenyl)-4-yl)boronic acid;
[0065] Dissolve 4'-bromo-N,N-bis(4-methoxyphenyl)-(1,1'-biphenyl)-4-amine (1012mg / 2.2mmol) in 15mL tetrahydrofuran solvent under nitrogen Protect and lower the temperature to -78°C, slowly add n-butyllithium n-hexane solution (1.5mL / 3.75mmol) with a concentration of 2.5mol / L with a syringe, stir the mixed solution at -78°C for 1h, and continue to add trim...
Embodiment 2
[0078] This embodiment provides a method for preparing a stellate tetraamine pyrene compound, comprising the following steps:
[0079] (1) Preparation of 4'-bromo-N,N-bis(4-methoxyphenyl)-(1,1'-biphenyl)-4-amine;
[0080] Refer to Example 1 for the specific preparation method.
[0081] (2) Preparation of (4'-(bis(4-methoxyphenyl)amino)-(1,1'-biphenyl)-4-yl)boronic acid;
[0082] Dissolve 4'-bromo-N,N-bis(4-methoxyphenyl)-(1,1'-biphenyl)-4-amine (459mg / 1mmol) in 6mL tetrahydrofuran solvent, under nitrogen protection Lower the temperature to -80°C, slowly add n-butyllithium n-hexane solution (0.6mL / 1.5mmol) with a concentration of 2.5mol / L with a syringe, stir the mixed solution at -80°C for 1h, and continue to add trimethyl borate ( 156mg / 1.5mmol), stirred for 2h, returned to 25°C and continued to react for 1h at room temperature, and added excess hydrochloric acid with a concentration of 5% until the boric acid precipitate disappeared. Extract the reaction system with dichl...
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