5-alkyl-2,3-dihydrobenzofuran-C60 fullerene bis-adduct and preparation method and application thereof

A double adduct, fullerene technology, applied in the field of material chemistry, can solve the problems of the arrangement affecting the mobility of carriers, reducing the effect, affecting the effect, etc., and achieving easy separation and purification, short reaction time, extremely high performance. The effect of scientific research and development and market investment value

Active Publication Date: 2015-12-16
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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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 th

Method used

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  • 5-alkyl-2,3-dihydrobenzofuran-C60 fullerene bis-adduct and preparation method and application thereof
  • 5-alkyl-2,3-dihydrobenzofuran-C60 fullerene bis-adduct and preparation method and application thereof
  • 5-alkyl-2,3-dihydrobenzofuran-C60 fullerene bis-adduct and preparation method and application thereof

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 2.80g (50mmol) KOH and 3.42g (20mmol) p-toluenesulfonamide to 80mL of anhydrous methanol, stir for 10min, then add 6.4g (20mmol) at 5°C ) Diacetoxyiodobenzene, stirred at 5°C for 0.5h, returned to room temperature and then reacted for 3h, poured the clear solution into the ice-water mixture to obtain a light yellow solid TsN=IPh crude product, filtered with a sand core The device was filtered, recrystallized with methanol, and vacuum-dried for 8 hours to obtain TsN=IPh, which was filled with nitrogen and stored in a refrigerator at 4°C until use. The yield was about 60%.

[0043]

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

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 2.80g (50mmol) KOH and 3.42g (20mmol) p-toluenesulfonamide to anhydrous methanol, stir for 10min, and o Add 6.4g (20mmol) diacetoxy iodobenzene at 5°C, stir for 0.5h at 5°C, return to room temperature and react for 3h, then pour the clear solution into ice-water mixture to obtain light yellow solid TsN=IPh crude product, filtered with a sand core filter, washed three times with ultrapure water and anhydrous ether, recrystallized with methanol, dried in vacuum for 8 hours to obtain TsN=IPh, filled with nitrogen and placed in a refrigerator at 4 °C Stored for later use, the yield is about 60%.

[0053] (2) In an argon atmosphere, add 3.6mg (0.036mmol) cuprous chloride, 6.0μL (0.072mmol) 2,6-lutidine into the flask, and then add 120mL of anhydrous o-dichlorobenzene, After stirring at room temperature for 30 min, 1.30 g (1.8 mmol) of ...

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 2.80g (50mmol) KOH and 3.42g (20mmol) p-toluenesulfonamide to anhydrous methanol, stir for 10min, then add 6.4g (20mmol) at 5°C Diacetoxyiodobenzene, stirred at 5°C for 0.5h, returned to room temperature and then reacted for 3h, poured the clear solution into the ice-water mixture to obtain a light yellow solid TsN=IPh crude product, filtered through a sand core Filter, wash with ultrapure water and anhydrous ether for 3 times, recrystallize with methanol, and dry in vacuum for 8 hours to obtain TsN=IPh, fill with nitrogen and store in a refrigerator at 4°C for later use, the yield is about 60% .

[0063] (2) In an argon atmosphere, add 3.6mg (0.036mmol) cuprous chloride, 6.0μL (0.072mmol) 2,6-lutidine into the flask, and then add 120mL of anhydrous o-dichlorobenzene, After stirring at room temperature for 30 min, 1.30 g (1.8 mmol)...

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Abstract

The invention discloses a 5-alkyl-2,3-dihydrobenzofuran-C60 fullerene bis-adduct and a preparation method and application thereof. The bis-adduct as shown in the formula (I) (R is methyl or ethyl or isopropyl or tertiary butyl or tertiary pentyl) can be prepared through the method including the following steps that (1) PhI=NTs is prepared, (2) a bis-addition intermediate is prepared, and (3) the target bis-adduct is prepared. The bis-adduct is low in resultant temperature, short in reaction time, prone to separation and purification, beneficial to mass production, good in optical adsorption property within the visible light range and suitable for being used as an electron acceptor material for building photovoltaic devices such as a photovoltaic cell, thereby having great scientific research, 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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IPC IPC(8): C07D493/08H01L51/46
CPCC07D493/08H10K85/215H10K85/653Y02E10/549Y02P70/50
Inventor 谌宁刘光鑫曹天天
Owner SUZHOU UNIV
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