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A 1,3,2-dithiazole free radical conjugated molecular material and its preparation method and application
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A free radical and bithiazole technology, applied in the field of 1,3,2-dithiazole radical conjugated molecular materials and its preparation, can solve problems such as toxicity, unfavorable compound preparation, and difficult compound synthesis, and achieve π-π stacking Strong ability, large degree of intermolecular aggregation, and environmentally friendly effects
Active Publication Date: 2015-10-28
INST OF CHEM CHINESE ACAD OF SCI
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[0005] However, due to the difficulty in synthesizing such compounds, and the traditional synthesis method uses mercaptan or chlorine gas, which has certain toxicity and is not conducive to the preparation of compounds.
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Embodiment 1
[0043] Example 1, Synthesis of 3-(trifluoromethyl)phenyl-1,3,2-bithiazole free radical
[0045] (1) Dissolve compound 1a (21.5g, 0.1mol) in N,N-dimethylformamide (150mL) at 100°C in a nitrogenatmosphere, then add sodium tert-butylthiolate (56g, 0.5mol), a substitution reaction occurred, stirred for 24 hours, then added water, extracted three times with dichloromethane (3*300mL), combined organic phases and dried over anhydroussodiumsulfate. After removing the solvent, the product 1b (0.075 mmol, 75%) was obtained by column separation with silica gel.
[0046] The structural confirmation data are as follows: 1 H NMR (400MHz, CDCl 3 )δ7.87(d, 1H, J=1.24Hz), 7.75(d, 1H, J=5.36Hz), 7.49(dd, 1H, J=5.36Hz, J=1.2Hz), 1.39(s, 9H) ,1.34(s,9H); Elemental analysis: The calculated value is C 13 h 21 f 3 S 2:C,52.32;H,7.09;Actual value:C,52.51;H,6.98;
[0047] (2) Dissolve...
Embodiment 2
[0053] Embodiment 2, the synthesis of 3,4-dicyano-phenyl-1,3,2-bithiazole free radical
[0055] (1) Dissolve compound 5a (28g, 0.1mol) in N,N-methylformamide (150mL) at 60°C in a nitrogenatmosphere, then add sodium isopropylthiolate (49g, 0.5mol ), the substitution reaction occurred, stirred for 16 hours, then added water, extracted three times with dichloromethane (3*200mL), the organic phases were combined and dried over anhydroussodium sulfate. After removing the solvent, the product 5b (0.064 mmol, 64%) was obtained by column separation with silica gel.
[0056] The structural confirmation data are as follows: 1 H NMR (400MHz, CDCl 3 )δ7.86 (s, 2H), 2.88 (m, 2H), 1.23 (s, 12H); elemental analysis: the calculated value is C 14 h 20 N 2 S 2 :C,60.83;H,5.83;Actual value:C,60.62;H,5.90;
[0057] (2) Dissolve the product 5b (5.5g, 20mmol) obtained in (1) in dich...
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Abstract
The invention discloses a 1,3,2-dithiazole free-radical conjugated molecule material and a preparation method and application thereof. 1,3,2-dithiazole free radical is represented by a formula I. The preparation method of the 1,3,2-dithiazole free radical represented by the formula I comprises the following steps of (1) using a compound represented by a formula V and R3SNa to perform substitution reaction to obtain a compound represented by a formula VI, (2) using the compound represented by the formula VI and dichloro iodobenzene to perform substitution reaction, then using a product and trimethyl siliconnitride to perform cyclization reaction to obtain a compound represented by the formula VII, (3) using the compound represented by the formula VII and a reducing agent to perform reduction reaction to obtain the 1,3,2-dithiazole free radical represented by the formula I. A 1,3,2-dithiazole free radical conjugated molecule and a derivative of the molecule contain self-spinning single electrons, so that the 1,3,2-dithiazole free-radical conjugated molecule material has magnetic property and has potential applicability in aspects of magnetic materials and self-spinning electronic devices.
Description
technical field [0001] The invention relates to a 1,3,2-dithiazole radical conjugated molecular material, a preparation method and application thereof. Background technique [0002] Organic molecular materials, also known as organic solids (Zhu Daoben, Wang Fosong. Organic solids. Shanghai: Shanghai Science and Technology Press, 1999), usually refer to organic optoelectronic materials with π-electronic structures and special optical, electrical, and magnetic properties, commonly known as organic semiconductors Material. In recent years, due to the unique properties of organic compounds, organic optoelectronic functional materials have increasingly highlighted its important position in the material science. In fact, since the 1970s, the research on optical, electrical and magnetic functional materials based on organic (polymer) molecules has been highly concerned by the scientific community and has become one of the research hotspots (the International Union of Pure and Appl...
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