Aggregation-induced emission near-infrared emission diketopyrrolopyrrole compound and preparation method thereof

A diketopyrrolopyrrole, aggregation-induced luminescence technology, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve problems such as scarcity of species, and achieve the effect of convenient derivatization and functionalization

Inactive Publication Date: 2018-11-30
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, most of DPPs with aggregation-induced luminescence are symmetrical

Method used

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  • Aggregation-induced emission near-infrared emission diketopyrrolopyrrole compound and preparation method thereof
  • Aggregation-induced emission near-infrared emission diketopyrrolopyrrole compound and preparation method thereof
  • Aggregation-induced emission near-infrared emission diketopyrrolopyrrole compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Preparation of aggregation-induced luminescent near-infrared emitting diketopyrrolopyrrole compound DPP1

[0034] (1) 3,6-dithienylpyrrolopyrrole diketone was prepared according to the method disclosed in literature Li F C, Qiao H B, Guo K, Zhou L, Chen X G, RSC Adv., 2014, 4, 58027-58035, 2 -(4-((Z)-1,2-bis(diethylamino)-2-styrene)phenyl-4,4,5,5-tetramethyl)boronic acid pinacol ester According to literature Shen X Y , prepared by the method disclosed in Wang Y J, ZhaoE, The J.of Phys.Chem.C, 2013, 117(14):7334-7347.

[0035] (2) In 20mmol of potassium tert-butoxide and 100mL of dry N-methylpyrrolidone solution, add 10mmol of 3,6-dithienylpyrrolopyrrole diketone and 10mmol of bromoisoctane, under argon protection Heat to reflux for 16h, cool to room temperature, filter with suction, and distill the filtrate under reduced pressure to remove most of N-methylpyrrolidone, then wash with water, CH 2 Cl 2 Extraction, anhydrous NaSO 4 Drying and column chromatog...

Embodiment 2

[0040] Example 2: Preparation of aggregation-induced luminescent near-infrared emitting diketopyrrolopyrrole compound DPP2

[0041] (1) 3,6-dithienylpyrrolopyrrole diketone was prepared according to the method disclosed in literature Li F C, Qiao H B, Guo K, Zhou L, Chen X G, RSC Adv., 2014, 4, 58027-58035, 2 -(4-((Z)-1,2-bis(dimethoxy)-2-styrene)phenyl-4,4,5,5-tetramethyl)boronic acid pinacol ester according to literature Hu F , prepared by the methods disclosed in Huang Y, Zhang G, Zhao R, Zhang D Q, Tetrahedron Lett.2014, 55, 1471-1474.

[0042] (2) In 20mmol of potassium tert-butoxide and 100mL of dry N-methylpyrrolidone solution, add 10mmol of 3,6-dithienylpyrrolopyrrole diketone and 10mmol of bromoisoctane, under argon protection Heat to reflux for 16h, cool to room temperature, filter with suction, and distill the filtrate under reduced pressure to remove most of N-methylpyrrolidone, then wash with water, CH 2 Cl 2 Extraction, anhydrous NaSO 4 Drying and column chro...

Embodiment 3

[0046] Example 3 Preparation of aggregation-induced luminescent near-infrared emitting diketopyrrolopyrrole compound DPP3

[0047] (1) 1) 3,6-dithienylpyrrolopyrrole diketone was prepared according to the method disclosed in literature Li F C, Qiao H B, Guo K, Zhou L, Chen X G, RSC Adv., 2014, 4, 58027-58035 , 2-(4-((Z)-1,2-bis(diethylamino)-2-styrene)phenyl-4,4,5,5-tetramethyl)boronic acid pinacol ester according to literature Prepared by the method disclosed in Shen X Y, Wang Y J, ZhaoE, The Journal of Physical Chemistry C, 2013, 117(14): 7334-7347.

[0048] (2) In 20mmol of potassium tert-butoxide and 100mL of dry N-methylpyrrolidone solution, add 10mmol of 3,6-dithienyldiketopyrrolopyrrole and 10mmol of bromododecane, under argon protection Heated to reflux for 5h, cooled to room temperature, suction filtered, and the filtrate was distilled off under reduced pressure to remove most of N-methylpyrrolidone, washed with water, CH 2 Cl 2 Extraction, anhydrous NaSO 4 Drying...

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Abstract

The invention discloses an aggregation-induced emission near-infrared emission diketopyrrolopyrrole compound and a preparation method thereof. The method comprises the steps that 3,6-dithiophene diketopyrrolopyrrole reacts with twice molar weight of alkyl bromide so as to obtain 2,5-dialkyl-3,6-dithienopyrrolopyrrole, then the 2,5-dialkyl-3,6-dithienopyrrolopyrrole sequentially undergoes Vilsmeierreaction with phosphorus oxychloride/N,N-dimethylformamide and undergoes substitution reaction with N-bromosuccinimide so as to obtain 2,5-dialkyl-3-(5-formyl)thienyl-6-(5-bromine)thienyl diketopyrrolopyrrole, and then the 2,5-dialkyl-3-(5-formyl)thienyl-6-(5-bromine)thienyl diketopyrrolopyrrole undergoes Suzuki reaction with tetraphenyl ethylene boric acid ester so as to obtain 2,5-dialkyl-3(4-((E)-2-phenyl-1,2-disubstituted styryl)phenyl)thienyl-6-(5-formyl)thienyl diketopyrrolopyrrole. The compound has the emission range greater than 650 nm and has the aggregation-induced emission property.

Description

technical field [0001] The invention belongs to the field of synthesis of fluorescent small molecule materials, and relates to an aggregation-induced luminescent near-infrared emitting diketopyrrolopyrrole compound and a preparation method thereof. Background technique [0002] Aggregation-induced fluorescence quenching (ACQ) is ubiquitous in organic aromatic compounds in fluorescent materials, which severely limits the application of organic fluorescent materials in high-efficiency optoelectronic devices, chemical sensors, and biological probes. Since Professor Tang Benzhong first proposed the concept of aggregation-induced emission (AIE), materials with aggregation-induced emission have attracted much attention [(1) J.Mei, N.L.C.Leung, R.T.K.Kwok, J.W.Y.Lam, B.Z.Tang, Chem.Rev., 2015, 115, 11718-11940; (2) Z.Chi, X.B.Zhang, Xu, X.Zhou, C.Ma, Y.Zhang, S.Liu, J.Xu, Chem.Soc.Rev ., 2012, 41, 3878-3896]. Compared with traditional ACQ fluorescent molecules, AIE molecules have...

Claims

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Application Information

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IPC IPC(8): C07D487/04C09K11/06
CPCC07D487/04C09K11/06C09K2211/1007C09K2211/1029C09K2211/1092
Inventor 汪凌云卓少春曹德榕
Owner SOUTH CHINA UNIV OF TECH
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