Bipyridine compound, synthetic method thereof, and flow battery system with bipyridine compound
A technology of bipyridines and synthesis methods, which is applied in the field of all-organic water-phase system liquid flow battery systems, can solve the problems of prone to water electrolysis side reactions, low operating current density, and easy cross-contamination of electrolytes, etc.
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[0053] According to the synthesis method of bipyridine compounds according to the embodiment of the present invention, the synthesis method comprises: reacting 4,4'-bipyridine with brominated alkanes to obtain the product bipyridine compounds, the chemical reaction formula of which is as follows: (A ) as shown:
[0054]
[0055] (A); wherein, the substituent R 1 , R 2 H, OH, OMe, OEt, CHO, NH 2 、N(Me) 2 , N(Et) 2 , F, Cl, Br, CN, NO 2 , COOH, SO 3 H or one of the grafted polymer compounds; n represents the length of the alkyl chain.
[0056] In other words, when preparing the product, 4,4'-bipyridyl and brominated alkanes can be mixed and put into the reactor, and react under certain conditions to obtain the product.
[0057] According to an embodiment of the present invention, n is one of 1-16, and the molecule of the bipyridyl compound has a symmetrical or asymmetrical structure.
[0058] In some specific embodiments of the present invention, in the chemical react...
Embodiment 1
[0086] Synthesis of 1,1'-bis(3-(trimethylamino)propyl)-[4,4'-bipyridyl]tetrabromosalt
[0087] Mix and dissolve 0.47g (3.0mmol) 4,4'-bipyridine and 1.27g (7.0mmol) (3-bromopropyl)trimethylammonium bromide in 30mL acetonitrile, slowly raise the temperature to reflux, and reflux for 24h A pale yellow solid was produced, and the reaction solution was left to stand overnight in the refrigerator. The precipitated product was filtered, washed and dried with ethanol, and recrystallized with methanol / ethanol (1:1, v / v) to obtain a solid. The product was characterized by NMR, and 1.43 g of the product was obtained with a yield of 92%.
[0088] The product obtained was a pale yellow solid, such as figure 2 with image 3 as shown, 1 H NMR (400MHz,D 2 O), δ9.25(d, J=7.0Hz, 4H), 8.67(d, J=6.9Hz, 4H), 5.04–4.85(m, 4H), 3.77–3.54(m, 4H), 3.24(s ,18H),2.87–2.60(m,4H); 13 C NMR (101MHz, D 2 O) δ 150.58, 145.73, 127.59, 62.43, 58.29, 53.30, 24.67.
Embodiment 2
[0090] Synthesis of 1-(3-(trimethylamino)propyl)-[4,4'-bipyridyl]tribromide
[0091] Mix and dissolve 0.47g (3.0mmol) 4,4'-bipyridyl and 0.54g (3.0mmol) (3-bromopropyl)trimethylammonium bromide in 30mL acetonitrile, slowly raise the temperature to reflux, and reflux for 24h A white solid was produced, and the reaction was left to stand overnight in the refrigerator. The precipitated product was filtered, washed and dried with ethanol, and recrystallized with methanol / ethanol (1:1, v / v) to obtain a solid. The product was characterized by NMR, and 0.91 g of the product was obtained with a yield of 90%.
[0092] The product obtained was a white solid, 1 H NMR (400MHz,D 2 O)δ9.10(d, J=6.9Hz, 2H), 8.90–8.63(m, 2H), 8.48(d, J=6.9Hz, 2H), 8.04–7.80(m, 2H), 4.86(t, J=7.7Hz, 2H), 3.78–3.49(m, 2H), 3.25(s, 9H), 2.89–2.46(m, 2H). 13 C NMR (101MHz, D 2 O) δ154.32, 150.02, 144.99, 142.27, 126.45, 122.55, 62.50, 57.73, 53.35, 24.66.
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