Novel viologen compound and its preparation
A compound and selected technology, applied in organic chemistry, chemical instruments and methods, color-changing fluorescent materials, etc., can solve the problem of very limited influence on the electrochemical properties of viologen derivatives, unfavorable regulation of the electron-accepting ability of viologen-like compounds, etc. question
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[0098] Preparation of Fully Conjugated Polyviologen Compound
[0099] The invention also provides a preparation method of the above-mentioned fully conjugated polyviologen compound.
[0100] In a preferred embodiment of the present invention, the preparation method of the compound of formula I includes the steps:
[0101]
[0102] (4a) In an inert solvent, use the compound of formula IIa and R-(Y) n+1 React to obtain a compound of formula Ib; and
[0103] (4b) Reacting a compound of formula Ib with a terminal alkylating reagent to obtain a compound of formula I.
[0104] Wherein, m=1, n is selected from 1, 2, 3;
[0105] The definitions of R and X are as described above;
[0106] Y is an amino group.
[0107] In another preferred embodiment, the terminal alkylating reagent is R 1 -M 1 And R 2 -M 2 ; Where R 1 , R 2 , M 1 , M 2 The definition of is as described above.
[0108] In another preferred example, in the step (4a), the compound of formula IIa and R-(Y) n+1 The molar ratio is 1~5:1. ...
Embodiment 1
[0158] Example 1: Synthesis of compound P12
[0159]
[0160] Step 1: Zincke salt 1 (5.37g, 15mmol), p-phenylenediamine (0.542, 5mmol) were added to 60mL ethanol, heated to reflux for 48 hours, cooled to room temperature, filtered, and the solid was dissolved in methanol. Then the above methanol solution was added dropwise to a large amount of acetone, the precipitate was separated out, filtered, the solid was washed with acetone, and dried to obtain the product. Gray solid (0.352g, yield 15%). 1 HNMR (400MHz, CD 3 OD) δ 9.52 (d, 4H), 8.92 (d, 4H), 8.80 (d, 4H), 8.35 (s, 4H), 8.14 (d, 4H). MS(ESI): m / z194.1[M-2Cl] 2+
[0161] Step 2: Add the compound obtained in Step 1 (0.233 g, 0.5 mmol) and methyl iodide (1 mL, 160 mmol) to 60 mL of acetonitrile. After heating to reflux for 72 hours, a large amount of red solid precipitated. The heating was stopped, after cooling to room temperature, the mixture was stirred overnight, filtered, and the obtained solid was washed with acetone an...
Embodiment 2
[0162] Example 2: Synthesis of compound P14
[0163]
[0164] Step 1: Zincke salt 1 (1.95g, 5.5mmol), 4,4'-diphenyldiamine (0.3g, 1.6mmol) were added to 120mL ethanol, heated to reflux for 12 hours, filtered, and the solid obtained was washed with acetone Then, add it to 100mL of anhydrous methanol to dissolve to obtain an orange-yellow solution, add NH 4 PF 6 After ion exchange and filtration, the solid product was washed with acetone and dried to obtain 0.192 g of hexafluorophosphate with a yield of 75%. 1 HNMR(400MHz,DMSO-d 6 ): 9.58 (d, 4H), 8.93 (d, 4H), 8.84 (d, 4H), 8.25 (d, 4H), 8.18 (d, 4H), 8.12 (d, 4H). 13 CNMR(100MHz,DMSO-d 6 ): 153.42,152.05,150.29,146.45,145.53,145.23,144.35,142.28,140.87,140.63,129.92,128.83,128.63,127.52,126.91,126.19,125.76,125.49,124.51,123.31,122.21,and120.94. MS(ESI): m / z[M-2Cl] 2+ 232.1. HRMS (MALDI-DHB) calculated value C 32 H 24 N 4 [M-2PF 6 ]: 464.20, experimental value: C 32 H 23 N 4 + 463.1917.
[0165] Step 2: The compound obtained in St...
PUM
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