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A double center boron fluoride complexed dipyrromethene derivative containing carbazole and bridging group in the middle position and its preparation method

A technology of dipyrromethene and bridging group, which is applied in the field of double-center boron fluoride complexed dipyrromethene derivatives and its preparation, can solve the problem of little change in molecular spectral properties, and achieve high comprehensive yield and synthesis low cost effect

Active Publication Date: 2018-06-19
DONGGUAN UNIV OF TECH
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

Studies have shown that after the introduction of aromatic functional groups at the meso-position of the BODIPY core, it is difficult to form effective conjugation with the BODIPY core plane, and the spectral properties of the molecule do not change much. Therefore, the current meso-position modified BODIPY dyes, especially meso There are very few reports on the double-center fluoroboron dyes modified by -position

Method used

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  • A double center boron fluoride complexed dipyrromethene derivative containing carbazole and bridging group in the middle position and its preparation method
  • A double center boron fluoride complexed dipyrromethene derivative containing carbazole and bridging group in the middle position and its preparation method
  • A double center boron fluoride complexed dipyrromethene derivative containing carbazole and bridging group in the middle position and its preparation method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Synthesis of BDP1.

[0038] (1) Synthesis of intermediate 1 (3,6-dibromocarbazole).

[0039] Add 4 g (24.0 mmol) of carbazole, 8.5 g (48.0 mmol) of N-bromosuccinimide, and 80 mL of anhydrous tetrahydrofuran into a 250 mL single-necked bottle, and heat the reaction system to 80 °C under the protection of argon Stir the reaction for 24 h, stop the reaction, pour the reaction mixture into 200 mL distilled water after cooling to room temperature, extract three times with ethyl acetate, wash the organic layer three times with saturated brine, combine the organic phases, and dry over anhydrous sodium sulfate overnight. The solvent was removed by rotary evaporation, and the residue was subjected to silica gel column chromatography using petroleum ether: ethyl acetate = 30:1 as the eluent to obtain 6.1 g of white solid with a yield of 78%. 1 H NMR (600MHz, CDCl 3 ) δ: 8.13 (s, 2H), 8.10 (s, 1H), 7.52 (d, J = 6.8 Hz, 2H), 7.30 (d, J = 8.6 Hz, 2H). 13 C NMR (151 MHz, CDCl ...

Embodiment 2

[0051] Synthesis of BDP2.

[0052] (1) Synthesis of intermediate 4b (3,6-bis(5-formylthienyl)-9-octylcarbazole).

[0053] Into a 100 mL three-necked flask, 2 g (3.8 mmol), 1.6 g (8.4 mmol) of 5-bromothiophene-2-carbaldehyde, intermediate 4b was obtained by a method similar to the synthesis of intermediate 4a, an orange-yellow fluorescent solid, and the yield was 68%. 1 H NMR (600 MHz, CDCl 3 ) δ: 8.41 (s, 2H),7.81 (d, J = 8.5 Hz, 2H), 7.77 (d, J = 3.8 Hz, 2H), 7.47 (d, J = 3.8 Hz, 2H), 7.44 (d, J = 8.5 Hz, 2H), 4.31 (t, J = 7.2 Hz, 2H), 1.93–1.84 (m, 2H), 1.39–1.22 (m, 10H), 0.86 (t, J = 6.9 Hz, 2H). 13 C NMR (151 MHz, CDCl 3 ) δ: 182.59, 155.71, 141.57, 137.78, 126.47, 125.16, 124.89, 123.26, 123.15, 118.69, 109.78, 43.54, 31.75, 29.31, 29.13, 22.020, 8.5

[0054] (2) Synthesis of intermediate 5b (3,6-bis[5-(dipyrrolemethyl)thienyl]-9-octylcarbazole).

[0055] Add 0.5 g (1 mmol) of 3,6-bis(5-formylthienyl)-9-octylcarbazole and 10.4 mL (150 mmol) of pyrrole to...

Embodiment 3

[0059] Synthesis of BDP3.

[0060] (1) Synthesis of intermediate 4c (3,6-bis(5-formylfuryl)-9-octylcarbazole).

[0061] Into a 100 mL three-necked flask, 2 g (3.8 mmol), 1.47 g (8.4 mmol) of 5-bromofuran-2-carbaldehyde, intermediate 4c was obtained by a method similar to that of intermediate 4a, an orange-yellow fluorescent solid, and the yield was 70.7%. 1 H NMR (600 MHz, CDCl 3 ) δ: 9.64 (s,2H), 8.53 (s, 2H), 7.89 (d, J = 8.5 Hz, 2H), 7.37 (t, J = 5.6 Hz, 4H), 6.85(d, J = 3.6 Hz, 2H), 4.23 (t, J = 7.2 Hz, 2H), 1.93–1.74 (m, 2H), 1.36–1.19(m, 10H), 0.86 (t, J = 7.0 Hz, 3H). 13 C NMR (151 MHz, CDCl 3 ) Δ: 176.73, 160.76,151.60, 141.51, 123.84, 123.09, 120.69, 118.03, 109.48, 106.39, 43.40, 31.75,29.29, 29.15, 27.23, 22.59, 14.07. forC 30 h 29 NO 4 : 467.210, found: 467.244 [M] + .

[0062] (2) Synthesis of intermediate 5c (3,6-bis[5-(dipyrrolemethyl)furyl]-9-octylcarbazole).

[0063] Using a method similar to the synthesis of intermediate 5a, intermediate ...

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Abstract

The invention discloses a double-center boron-dipyrromethene fluorophore (BODIPY) derivative with meso-position containing carbazole and bridging groups and a preparation method thereof. The preparation method comprises the following steps of using carbazole as an initial raw material; performing brominating and N-octyl reaction, performing Suzuki coupling reaction with bisdiboron, and then respectively reacting with 4-bromobenzaldehyde, 5-bromothiophene-2-formaldehyde, 5-brominated furan-2-formaldehyde and the like, so as to obtain a twain-aldehyde compound; reacting with pyrrole, and synthesizing into a di-(dipyrrolidine) compound; finally, performing fluoride boronizing by boron trifluoride diethyl etherate, so as to obtain several novel double-center BODIPY dyes containing carbazole and different bridging groups. After carbazole and five-membered heterocycle thiophene and furan are introduced into the double-center BODIPY structure, the red shift of ultraviolet absorption of the derivative is generated, and the stability is good. The preparation method has the advantages that the preparation method is simple, the yield rate is high, the synthesizing is highly efficient, and the preparation method can be widely applied.

Description

technical field [0001] The invention relates to a double-centered boron fluoride complexed dipyrromethene derivative containing carbazole and a bridging group in the middle position and a preparation method thereof. The derivative can be applied to fluorescent dyes, luminescent materials, photovoltaic materials, life Science, Analytical Science, Environmental Energy Science and other fields. Background technique [0002] Boron fluoride complexed dipyrromethene (4,4′-Difluoro-4-bora-3a,4a-diaza-sindacene, referred to as BODIPY) fluorescent dyes have been widely concerned since they were first reported in 1968, because of their relatively High photostability and strong spectral absorption have been used in life sciences, analytical chemistry, environmental energy science and other fields. [0003] In order to obtain new BODIPY derivative materials with excellent performance, many researchers choose to modify the pyrrole ring of the BODIPY core to extend the conjugation length...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09B23/12
CPCC07F5/02C09B23/12
Inventor 赵鸿斌廖俊旭韩利芬王育才张文涛刘啸天刘传生黄国鑫
Owner DONGGUAN UNIV OF TECH
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