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Imide fluoranthene molecular building block as well as preparation and application thereof

A technology of imide fluoranthene and imide, applied in the field of organic photoelectric materials, to achieve the effect of obvious aggregation-induced fluorescence enhancement effect

Pending Publication Date: 2022-03-18
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The 2,3-imide fluoranthene molecular building block in the present invention successfully solves the problem of aggregation fluorescence quenching in the current highly planar imide molecules (such as pyrene diimide and naphthalene diimide compounds) problems, and can be applied in fields such as bioimaging

Method used

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  • Imide fluoranthene molecular building block as well as preparation and application thereof
  • Imide fluoranthene molecular building block as well as preparation and application thereof
  • Imide fluoranthene molecular building block as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Synthesis of Compound F1: The synthetic route is as follows figure 1 shown.

[0079] Synthesis of intermediate 3

[0080] Compound 1 (2.83g, 8.0mmol), 2-ethylhexyl-maleimide (1.70g, 8.1mmol), p-toluenesulfonic acid (138mg, 0.8mmol) and 15mL of nitrobenzene were added to a 50mL Schlenk bottle , heated to 160-180°C for 6-10h. After the reaction solution was cooled to room temperature, it was added dropwise into methanol solution, and the crude product was obtained by filtration, recrystallized in methanol, filtered, and dried to obtain 2.0 g of a yellow solid with a yield of about 46.3%. 1 H NMR (600MHz, Chloroform-d) δ8.28(s, 1H, ArH), 8.07(d, J=7.4Hz, 1H, ArH), 8.02(d, J=1.7Hz, 1H, ArH), 7.73( d,J=7.4Hz,1H,ArH),7.68(d,J=8.0Hz,1H,ArH),7.57(dd,J=8.0,1.7Hz,1H),3.67(d,J=7.4Hz,2H ,-CH 2 -),1.96–1.87(m,1H,),1.41–1.29(m,8H,-CH 2 -),0.95(t,J=7.4Hz,3H,-CH 3 ),0.90(t,J=7.0Hz,3H,-CH 3 ).

[0081] Synthesis of Intermediate 6

[0082] in N 2 Under conditions, the intermed...

Embodiment 2

[0086] Synthesis of Compound F2: The synthetic route is as figure 1 shown.

[0087] Synthesis of intermediate 7

[0088] The synthesis method of intermediate 7 is the same as that of intermediate 6. The starting materials were intermediate 3 (676mg, 1.25mmol), 2,5-di(n-butyltin)-3,4-difluorothiophene (223mg, 0.50mmol) and Pd(PPh 3 ) 4 (58mg, 0.05mmol), the reaction temperature was 90°C, the reaction time was 48h, and the yield was 65.4%. 1 H NMR (600MHz, Chloroform-d)δ8.33(s,2H,ArH),8.10–8.07(m,2H,ArH),8.02(d,J=7.2Hz,2H,ArH),7.97(d,J =7.2Hz,2H,ArH),7.78–7.74(m,2H,ArH),7.61(dd,J=8.0,1.8Hz,2H,ArH),3.60(d,J=7.3Hz,4H,-CH 2 -), 1.85(t, J=6.2Hz, 2H), 1.38–1.29(m, 16H, -CH 2 -),0.92(t,J=7.5Hz,6H,-CH 3 ),0.85(t,J=7.0Hz,6H,-CH 3 ).13C NMR(101MHz,Chloroform-d)δ168.48,167.22,142.57,141.81,139.51,137.86,137.31,136.35,136.13,135.71,132.29,129.07,127.84,125.86,124.72,122.96,122.77,122.21,119.11,113.99 ,42.32,37.24,31.89,31.88,31.55,29.97,29.65,29.60,29.32,29.29,26.43,22.65,22.62,14...

Embodiment 3

[0092] The synthesis of compound F3, synthetic route such as figure 1 shown.

[0093] Synthesis of Intermediate 9

[0094] Compound 3 (676mg, 1.25mmol), Pd(PPh 3 ) 4 (43mg, 0.04mmol) and dry toluene (20mL) were added to a 50mL dry Schlenk bottle, the reaction solution was heated to 70-80°C, and 2,5-bis(tri-n-butyltin)thiophene (571mg, 1.25 mmol) in dry toluene (10 mL), after the dropwise addition was completed, the reaction was continued for 24-30 hours. After cooling, water and dichloromethane were added for extraction, dried, spin-dried and separated through a silica gel column to obtain 248 mg of an orange solid with a yield of 31.6%. 1 H NMR (600MHz, Chloroform-d) δ8.29(s, 1H, ArH), 8.07(d, J=1.7Hz, 1H, ArH), 7.94(d, J=7.2Hz, 1H, ArH), 7.77( d,J=7.2Hz,1H,ArH),7.72(d,J=8.0Hz,1H,ArH),7.58(dd,J=8.0,1.8Hz,1H,ArH),6.91(d,J=3.4Hz ,1H),6.84(d,J=3.5Hz,1H),3.52(d,J=7.3Hz,2H,-CH 2 -),2.90(t,J=7.7Hz,2H,-CH 2 -), 1.75(t, J=7.6Hz, 2H-CH 2 -),1.45(t,J=7.5Hz,2H,-CH 2 -),1.36–1....

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Abstract

The invention belongs to the field of organic photoelectric materials, and discloses an imide fluoranthene molecular building block and preparation and application thereof, in the imide fluoranthene molecular building block, imide substitution sites are the second site and the third site of fluoranthene molecular substituent serial numbers, and the imide fluoranthene molecular building block can be particularly applied to construction of N-type organic semiconductor materials or P-type organic semiconductor materials. According to the present invention, the imide fluoranthene with the specific chemical structure is utilized, the imide substitution site in the molecule is the 2, 3-site of fluoranthene, and the asymmetric molecular structure is provided, such that the novel imide fluoranthene (i.e., 2, 3-imide fluoranthene) can be used as the molecular building block to construct the N-type or P-type organic semiconductor, and has the aggregation-induced fluorescence enhancement effect.

Description

technical field [0001] The invention belongs to the field of organic photoelectric materials, and more specifically relates to an imide fluoranthene molecular building block, its preparation and application. Background technique [0002] Organic semiconducting materials are of great importance for next-generation flexible and printed optoelectronic devices and biomedicine. Among them, the electron donor-acceptor (D-A) type conjugated system has attracted the most attention, which can adjust the material properties by changing the combination of donor and acceptor units. Pyrelimide and naphthalimide are currently the most widely used areneimide acceptor building blocks, which have the advantages of simple synthesis, good planarity and low lowest unoccupied molecular orbital (LUMO) energy level. However, the development of acceptor units lags far behind that of donor units due to the reduced reactivity resulting from the introduction of electron-withdrawing groups. [0003] ...

Claims

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Application Information

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IPC IPC(8): C07D209/70C07D409/14C08G61/12C09K11/06
CPCC07D209/70C07D409/14C09K11/06C08G61/126C09K2211/1029C09K2211/1092C09K2211/1466C09K2211/1458C08G2261/124C08G2261/3223C08G2261/522C08G2261/92Y02E10/549
Inventor 李忠安孙祥浪
Owner HUAZHONG UNIV OF SCI & TECH
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