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A 5‑alkyl‑2,3‑dihydrobenzofuran‑c 60 Fullerene double adduct and its preparation method and use

A technology of double adducts and fullerenes, applied in the field of material chemistry, can solve the problems of arrangement affecting carrier mobility, effect, and effect reduction, and achieves easy separation and purification, short reaction time, and extremely The effect of R&D and market investment value

Active Publication Date: 2017-08-01
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The addition of substituent groups can effectively reduce the C 60 The electronic conjugated system of fullerene can further increase its LUMO energy level, but the steric effect caused by the substituent group will reduce the interaction between molecules, affect the arrangement of molecules and thus affect its carrier mobility, and then affect its function as a receptor material

Method used

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  • A 5‑alkyl‑2,3‑dihydrobenzofuran‑c  <sub>60</sub> Fullerene double adduct and its preparation method and use
  • A 5‑alkyl‑2,3‑dihydrobenzofuran‑c  <sub>60</sub> Fullerene double adduct and its preparation method and use
  • A 5‑alkyl‑2,3‑dihydrobenzofuran‑c  <sub>60</sub> Fullerene double adduct and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: 5-isopropyl-2,3-dihydrobenzofuran-C 60 Preparation of fullerene bis-adducts (BFCBA1).

[0042] (1) In an argon atmosphere, add 2.80 g (50 mmol) KOH and 3.42 g (20 mmol) p-toluenesulfonamide to 80 mL of anhydrous methanol, stir for 10 min, then add 6.4 g (20 mmol) diacetoxyiodobenzene, stirred at 5°C for 0.5 h, returned to room temperature and then reacted for 3 h, then poured the clear solution into ice-water mixture to obtain the crude product TsN=IPh as light yellow solid, Filter with a sand core filter, recrystallize with methanol, and dry in vacuum for 8 h to obtain TsN=IPh. Fill it with nitrogen and store it in a refrigerator at 4 °C until use. The yield is about 60%.

[0043]

[0044] (2) In an argon atmosphere, add 3.6 mg (0.036 mmol) of cuprous chloride and 6.0 μL (0.072 mmol) of 2,6-lutidine into the flask, and add it to 120 mL of anhydrous o-dichlorobenzene , after stirring for 30 min at room temperature, 1.30 g (1.8 mmol) of C 60 and 1.68 g (...

Embodiment 2

[0051] Example 2: 5-tert-butyl-2,3-dihydrobenzofuran-C 60 Preparation of fullerene bis-adducts (BFCBA2).

[0052] (1) In an argon atmosphere, add 2.80 g (50 mmol) KOH and 3.42 g (20 mmol) p-toluenesulfonamide to anhydrous methanol, stir for 10 min, and o Add 6.4 g (20 mmol) diacetoxyiodobenzene at 5°C, stir for 0.5 h at 5°C, and react for 3 h after returning to room temperature. Pour the clear solution into the ice-water mixture to obtain light yellow The solid TsN=IPh crude product was filtered with a sand core filter, washed three times with ultrapure water and anhydrous ether, recrystallized with methanol, and dried in vacuum for 8 hours to obtain TsN=IPh, which was filled with nitrogen and placed in 4 Stored in a refrigerator at ℃ for later use, the yield is about 60%.

[0053] (2) In an argon atmosphere, add 3.6 mg (0.036 mmol) cuprous chloride, 6.0 μL (0.072 mmol) 2,6-lutidine into the flask, and then add 120 mL of anhydrous o-dichlorobenzene , after stirring for 30 m...

Embodiment 3

[0061] Example 3: 5-tert-amyl-2,3-dihydrobenzofuran-C 60 Preparation of fullerene bis-adducts (BFCBA3).

[0062] (1) In an argon atmosphere, add 2.80 g (50 mmol) KOH and 3.42 g (20 mmol) p-toluenesulfonamide to anhydrous methanol, stir for 10 min, then add 6.4 g (20 mmol) diacetoxyiodobenzene, stirred at 5°C for 0.5 h, returned to room temperature and then reacted for 3 h, then poured the clear solution into ice-water mixture to obtain the crude product TsN=IPh as light yellow solid, Filter with a sand core filter, wash with ultrapure water and anhydrous ether three times, recrystallize with methanol, and vacuum-dry for 8 h to obtain TsN=IPh, which is filled with nitrogen and stored in a refrigerator at 4 °C for later use. The yield is about 60%.

[0063] (2) In an argon atmosphere, add 3.6 mg (0.036 mmol) cuprous chloride, 6.0 μL (0.072 mmol) 2,6-lutidine into the flask, and then add 120 mL of anhydrous o-dichlorobenzene , after stirring for 30 min at room temperature, 1.3...

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Abstract

The invention discloses a 5-alkyl-2,3-dihydrobenzofuran-C 60 Fullerene double adducts and their preparation and use. Diadducts (where R is methyl, ethyl, isopropyl, tert-butyl or tert-amyl) as shown in general formula (I) can be prepared by a method comprising the following steps: 1) preparing p-methyl benzenesulfonylimide iodobenzene; 2) preparation of double-addition intermediates; and 3) preparation of target double-adducts. The double adduct of the present invention has low synthesis temperature, short reaction time, easy separation and purification, and is conducive to large-scale production; it has good light absorption characteristics in the visible light range, and is suitable as an electron acceptor material to construct photovoltaic devices such as solar cells. , with great research and development and market investment value.

Description

technical field [0001] The invention belongs to the field of material chemistry and relates to a 5-alkyl-2,3-dihydrobenzofuran-C 60 Fullerene double adducts, methods for their preparation, and their use as acceptor materials in the preparation of photovoltaic devices. Background technique [0002] C 60 Fullerene has a three-dimensional large π-electron system. Due to its electron-deficient characteristics, it has good electron-accepting properties and high electron mobility, and is a good n-type semiconductor material. In addition, it is very easy to undergo addition reaction, so it can be used to prepare various functional derivatives. by C 60 Derivatization of fullerene can further adjust its optical properties, electrochemical properties, solubility in organic solvents, and compatibility with other materials. In recent years, C 60 Fullerenes and their derivatives have been widely used in organic optoelectronic devices such as polymer solar cells and field effect tran...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/08H01L51/46
CPCC07D493/08H10K85/215H10K85/653Y02E10/549Y02P70/50
Inventor 谌宁刘光鑫曹天天
Owner SUZHOU UNIV