1,4,5,8-naphthalenetetracarboxylic imide derivative bifluorescent material and method of preparing the same

A technology of naphthalene tetracarboxylic acid diimide and dual fluorescence, which is applied in the fields of luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problem of low quantum yield and achieve the effect of high thermal stability

CN101508893BInactive Publication Date: 2012-10-03ANHUI UNIVERSITY
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Publication Date
2012-10-03
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention relates to a 1,4,5,8-naphthalenetetracarboxylic acid diimide derivative bifluorescence material which has a chemical name of N-(2-ethylhexyl)-N-R- naphthalenetetracarboxylic formyl diimide compound and has a chemical formula; in the formula, R is selected from an a structural formula. A preparation method of the bifluorescence material takes naphthalene tetracarboxylic acid dianhydride of industrial product as raw materials which are first imidized with 2-ethyl-hexylamine to obtain an intermediate (1) N-(2-ethylhexyl)-naphthalene-1,8-dimethyl benzene anhydride-4,5-dicarboximide, and then the intermediate (1) is respectively imidized with 4-amino-1,2,4-triazole or 2-aminopyridine or 2-amino-4,6-dimethylpyrimidine to obtain a target product, and the imidization is that the raw materials are reacted for at least 5 hours at 140-160 DEG C under the protection of nitrogen in organic solvent and in the presence of catalyst zinc acetate.
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Description

1. Technical field

[0001] The present invention relates to an organic dual fluorescent material and a preparation method thereof, in particular to a class of organic dual fluorescent material with electrochemiluminescent properties and a preparation method thereof, specifically a naphthalene diimide dual fluorescent material and its preparation method. Preparation. 2. Background technology

[0002] Naphthalene diamide derivatives are used in photosynthesis (R.F.Kelley, M.J.Tauber and M.R.Wasielewski, J.Am.Chem.Soc., 2006, 128, 4779), solar cells (M.Tasior, D.T.Gryko, M.Cembor, J.S.Jaworski, New J.Chem., 2007, 31, 247), field Effect transistors (Y.Ofir, A.Zelichenok and S.Yitzchaik, J.Mater.Chem., 2006, 16, 2142), gas storage (K.L.Mulfort and J.T.Huppand, J.Am.Chem.Soc., 2007, 129, 9604), biosensors (H.S.Cao, V.Chang, R.Hernandez and M.D.Heagy, J.Org.Chem., 2005, 70, 4929), anticancer drugs (Y.Chu, S.Sorey, D.W.Hoffman and B.L. Iverson, J.Am.Chem.Soc., 2007, 129, 1304) and...

Examples

Embodiment Construction

[0044] Taking R as 4,6-dimethylpyrimidine as an example, non-limiting examples are described as follows:

[0045] 1. Refining of raw materials of naphthalene tetracarboxylic dianhydride: heating and dissolving the purchased industrial-grade naphthalene tetracarboxylic dianhydride raw material with KOH aqueous solution, and then recrystallizing with ethanol to obtain crystalline potassium salt of naphthalene tetracarboxylic acid, which is dissolved in an appropriate amount of water Use hydrochloric acid to adjust the pH of the solution to <3, and a large amount of white precipitates are produced. The precipitates are separated, and the precipitates are vacuum-dried to obtain relatively pure yellow naphthalene tetracarboxylic dianhydride powder.

[0046] 2. Preparation of intermediate (1):

[0047] Get 2.00g (7.46mmol) of refined naphthalene tetracarboxylic dianhydride in a three-necked flask, add 20mL DMF, 13mg (0.07mmol) zinc acetate, in N 2 When heated to ≥100° C. under prot...