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Conjugated alkynyl anthracene derivative as well as preparation method and application thereof

A technology for conjugated alkynyl anthracene and derivatives, which is applied in the field of conjugated alkynyl anthracene derivatives, can solve problems such as unfavorable application, isomerization and photooxidation, and achieve the effect of stable photochemical properties

Inactive Publication Date: 2019-03-08
安庆北化大科技园有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the carbon-carbon double bond is an effective conjugated bridge, it is prone to isomerization and photooxidation, and these shortcomings are not conducive to the further application of this type of material.

Method used

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  • Conjugated alkynyl anthracene derivative as well as preparation method and application thereof
  • Conjugated alkynyl anthracene derivative as well as preparation method and application thereof
  • Conjugated alkynyl anthracene derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] This embodiment discloses a conjugated alkynyl anthracene derivative, the synthesis method of which is as follows:

[0031]

[0032] Weigh 9,10-dibromoanthracene (1.01g, 3mmol), cuprous iodide (28.5mg, 0.15mmol), triphenylphosphine (39.3mg, 0.15mmol), bis(triphenylphosphine) dichloride Palladium (21.1 mg, 0.01 mmol) was added to a 100 ml three-neck flask equipped with a magnet and a thermometer, and 20 ml of DMF and 15 ml of TEA (triethylamine) were added to dissolve it. Weigh phenylacetylene (0.765g, 7.5mmol), dissolve it with 10ml DMF, and transfer it to a constant pressure dropping funnel. Vacuumize and fill with nitrogen three times under electromagnetic stirring, then raise the temperature to 80°C at 5°C / min, continue stirring for half an hour, and then start to add the DMF solution of phenylacetylene dropwise. TCL monitors that the 9,10-dibromoanthracene raw material reacts completely and then stops heating, and the reaction solution cools down to room tempera...

Embodiment 2

[0036] This embodiment discloses a conjugated alkynyl anthracene derivative, the synthesis method of which is as follows:

[0037]

[0038] Weigh 9,10-dibromoanthracene (1.01g, 3mmol), cuprous iodide (28.5mg, 0.15mmol), triphenylphosphine (39.3mg, 0.15mmol), bis(triphenylphosphine) dichloride Palladium (21.1 mg, 0.01 mmol) was added into a 100 ml three-neck flask equipped with a magnet and a thermometer, and 20 ml of DMF and 15 ml of TEA were added to dissolve it. N-dodecyl-3-ethynylcarbazole (1.43g, 7.5mmol) was weighed, dissolved in 10ml of DMF and transferred to a constant pressure dropping funnel. Under electromagnetic stirring, evacuate and inflate with nitrogen three times, then raise the temperature to 80°C at 5°C / min, continue stirring for half an hour, and start to add the DMF solution of N-dodecyl-3-ethynylcarbazole dropwise. TCL monitors that the 9,10-dibromoanthracene raw material reacts completely and then stops heating, and the reaction solution cools down to...

Embodiment 3

[0043] This embodiment discloses a conjugated alkynyl anthracene derivative, the synthesis method of which is as follows:

[0044]

[0045] Weigh 9,10-dibromoanthracene (1.01g, 3mmol), cuprous iodide (28.5mg, 0.15mmol), triphenylphosphine (39.3mg, 0.15mmol), bis(triphenylphosphine) dichloride Palladium (21.1 mg, 0.01 mmol) was added into a 100 ml three-neck flask equipped with a magnet and a thermometer, and 20 ml of DMF and 15 ml of TEA were added to dissolve it. N-dodecyl-3-ethynylphenothiazine (2.94 g, 7.5 mmol) was weighed, dissolved in 10 ml of DMF and transferred to a constant pressure dropping funnel. Vacuumize and inflate with nitrogen three times under electromagnetic stirring, then raise the temperature to 80°C at 5°C / min, and start to add the DMF solution of N-dodecyl-3-ethynylphenothiazine dropwise after continuous stirring for half an hour. TCL monitors that the 9,10-dibromoanthracene raw material reacts completely and then stops heating, and the reaction solu...

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Abstract

The invention discloses a conjugated alkynyl anthracene derivative. The structural formula of the conjugated alkynyl anthracene derivative is as shown in the description, wherein R1 and R2 are any oneof the following structural formulas; and R represents H or one of C1-C30 alkyl groups or one of C1-C30 alkoxy groups. The invention also discloses a preparation method and application of the conjugated alkynyl anthracene derivative. The conjugated alkynyl anthracene derivative has the advantages of being rigid in structure and stable in photochemical property.

Description

technical field [0001] The invention relates to the technical field of conjugated alkynyl anthracene derivatives, in particular to a conjugated alkynyl anthracene derivative, a preparation method and an application thereof. Background technique [0002] Two-photon absorption is a nonlinear optical phenomenon, which is defined as a phenomenon in which a molecule absorbs the energy of two photons through an intermediate virtual state and transitions from the ground state to a high-energy state. Long-wavelength lasers have the advantages of high processing precision and strong penetration, so compounds with two-photon absorption capabilities are widely used in three-dimensional information storage, two-photon photopolymerization, photodynamic therapy and other fields. The introduction of large conjugated systems, good symmetric structures, and strong electron donors can significantly improve the two-photon absorption properties of molecules. [0003] Anthracycline is a large r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C1/26C07C15/60C07D209/86C07D279/22C07C209/74C07C211/54C09K11/06C08F120/14
CPCC07C15/60C07C211/54C07D209/86C07D279/22C08F120/14C08F2438/01C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1037
Inventor 王涛薛探龙
Owner 安庆北化大科技园有限公司
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