Unlock instant, AI-driven research and patent intelligence for your innovation.

n,n'-dialkyl-14h-benzo[4,5]isoquinolino[2,1-a]naphthalene-14-one-3,4,10,11-di Imide compound and its preparation method and application

A technology of naphthalimide and compound, applied in N,N'-dialkyl-14H-benzo[4,5]isoquinolino[2,1-a]naphthalene- 14-keto-3,4,10,11-imide compound and its preparation and application fields can solve problems affecting molecular stacking, large synthesis difficulty, and molecular skeleton plane distortion

Active Publication Date: 2016-03-16
INST OF CHEM CHINESE ACAD OF SCI
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method is very difficult to synthesize, and the electron-withdrawing group is likely to cause distortion of the molecular skeleton plane and affect molecular packing.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • n,n'-dialkyl-14h-benzo[4,5]isoquinolino[2,1-a]naphthalene-14-one-3,4,10,11-di Imide compound and its preparation method and application
  • n,n'-dialkyl-14h-benzo[4,5]isoquinolino[2,1-a]naphthalene-14-one-3,4,10,11-di Imide compound and its preparation method and application
  • n,n'-dialkyl-14h-benzo[4,5]isoquinolino[2,1-a]naphthalene-14-one-3,4,10,11-di Imide compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1, the preparation of compound N-n-octyl-4,5-diamino-1,8-naphthalimide shown in formula V

[0055] 1) 4-nitro-1, the synthesis of 8-naphthalene dioic anhydride (compound of formula II)

[0056] Add 150ml of glacial acetic acid and 44.8g (150mmol) sodium dichromate into a 250ml three-necked flask, then add 6g (10mmol) of 5-nitroacenaphthene in batches, and the mixture is cooled to room temperature after stirring at reflux for 10 hours, and poured into In 500ml of ice water, a yellow solid was precipitated, filtered with suction, the filter cake was washed with water until neutral, and dried in the air. 4.2 g of 4-nitro-1,8-naphthalene dioic anhydride was obtained. Yield 57%

[0057] The structural characterization data are as follows:

[0058] Mass spectrum: [MS(EI)] m / z: 243 (M + ).

[0059] H NMR spectrum: 1 HNMR (d6-DMSO, 400MHz): δ8.75(d, J=8.8Hz, 1H), 8.66(d, J=7.2Hz, 1H), 8.63(d, J=8.4Hz, 1H), 8.56(d , J=8.0Hz, 1H), 8.12(t, J=8.0Hz, 1H).

[0060] NM...

Embodiment 2

[0081] Example 2, preparation of compound N-(2-hexyl)decyl-4,5-diamino-1,8-naphthalimide shown in formula V

[0082] 1) 4-nitro-1, the synthesis of 8-naphthalene dioic anhydride (compound of formula II)

[0083] Add 150ml of glacial acetic acid and 44.8g (150mmol) of sodium dichromate into a 250ml three-necked flask, and then add 6g (30mmol) of 5-nitroacenaphthene in batches. After the mixture is stirred at reflux for 10 hours, it is cooled to room temperature and poured into In 500ml of ice water, a yellow solid was precipitated, filtered with suction, the filter cake was washed with water until neutral, and dried in the air. 4.2 g of 4-nitro-1,8-naphthalene dioic anhydride was obtained. Yield 57%

[0084] The structural characterization data are as follows:

[0085] Mass spectrum: [MS(EI)] m / z: 243 (M + ).

[0086] H NMR spectrum: 1 HNMR (d6-DMSO, 400MHz): δ8.75(d, J=8.8Hz, 1H), 8.66(d, J=7.2Hz, 1H), 8.63(d, J=8.4Hz, 1H), 8.56(d , J=8.0Hz, 1H), 8.12(t, J=8.0Hz, 1H). ...

Embodiment 3

[0108] Embodiment 3, the synthesis of compound N-(2-hexyl)decyl-4,5-imide-1,8-naphthoic anhydride shown in the preparation formula VI

[0109] Under the protection of nitrogen, add 2g of 1,4,5,8-naphthalene tetracarboxylic anhydride and 50mL of anhydrous N,N-dimethylformamide into a 100mL three-necked flask. After heating up to 140°C, add 1.8g of 2-hexyldecylamine dropwise DMF solution. The dripping rate is slow, and the dripping is finished in three hours. Stirring was continued for 5 hours at 140°C. The reaction solution was cooled to room temperature, poured into 200 mL of water, extracted with 150 mL of dichloromethane, and the organic phase was washed 5 times with 100 mL of saturated sodium chloride solution. After drying with anhydrous sodium sulfate, spin dry. Column chromatography, with petroleum ether to dichloromethane=1:1 (V / V) as eluent, the product was passed through to obtain 1.4g of N-(2-hexyl)decyl-4,5-imide-1 , 8-Naphthoic anhydride. Yield 36%.

[0110] ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
melting pointaaaaaaaaaa
Login to View More

Abstract

The invention discloses a N,N'-dialkyl-14H-benzo[4,5]isoquinolino[2,1-a]perimidine-14-one-3,4,10,11-diimide (BIPOI) compound, and a preparation method and an application thereof. The compound has a structure as shown in formula I, wherein R and R' are alkyls or aryls. The invention also provides a preparation method of the compound in formula I. The synthetic route provided in the invention is simple and effective; raw materials are commercialized cheap products, which realizes low synthesis cost; the synthetic method has universality, and can be popularized and applied to synthesis of other BIPOI compounds. An OFET prepared by using the BIPOI of the invention as an organic semiconductor layer has higher electron mobility and on / off ratio ( the maximum of mu is 0.05 cm2 / V.s, and the on / off ratio is larger than 108), and the BIPOI of the invention has good application prospects in OFET.

Description

technical field [0001] The present invention relates to N,N'-dialkyl-14H-benzo[4,5]isoquinolino[2,1-a]phthalazin-14-one-3,4,10, 11-diimide compound and its preparation method and application. Background technique [0002] Many molecules with system conjugation are widely used in organic solar energy, organic field-effect transistor (OFET) and organic light-emitting diodes (Barbarella, G.; Melucci, M.; Sotgiu, G.Adv.Mater., 2005, 17, 1581; Katz, H.E. Chem. Mater. 2004, 16, 4748; Sirringhaus, H.; Tessler, N.; Friend, H.R. Science 1998, 280, 1741), a great deal of scientific research has been done on this class of molecules. Among these applications, OFET has good application prospects in the fields of electronic paper, memory, and sensor devices due to its low cost, good flexibility, and solution processing. [0003] The key components of OFET - organic semiconductor materials are divided into p-type and n-type materials according to the transmission type. Excellent p-type ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/22C07D221/14C07D491/06H01L51/30
Inventor 于贵朱敏亮张骥陈华杰黄剑耀郭云龙刘云圻
Owner INST OF CHEM CHINESE ACAD OF SCI