2-[(N- alkyl carbazolyl) vinyl]-1, 8-naphthyridine derivative as well as preparation method and application thereof

A technology of alkylcarbazolyl and vinyl, which is applied in the field of 2-[(N-alkylcarbazolyl)vinyl]-1,8-naphthyridine derivatives and their preparation and application, and can solve the problem of thermal stability Problems such as poor sex and photochemical stability, long molecular synthesis route, and low efficiency can achieve good photochemical stability, increase molecular two-photon absorption performance, and good thermal stability.

Inactive Publication Date: 2013-02-27
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0005] The purpose of the present invention is to solve the problems of long molecular synthesis route, low efficiency, poor thermal stability and photochemical stability of the large conjugated system in the existing two-photon absorption materials, and provides 2-[(N-alkylcarba Azolyl)vinyl]-1,8-naphthyridine derivatives and their preparation methods and applications

Method used

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  • 2-[(N- alkyl carbazolyl) vinyl]-1, 8-naphthyridine derivative as well as preparation method and application thereof
  • 2-[(N- alkyl carbazolyl) vinyl]-1, 8-naphthyridine derivative as well as preparation method and application thereof
  • 2-[(N- alkyl carbazolyl) vinyl]-1, 8-naphthyridine derivative as well as preparation method and application thereof

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specific Embodiment approach 1

[0028] Specific embodiment 1: The structural formula of the 2-[(N-alkylcarbazolyl)vinyl]-1,8-naphthyridine derivative in this embodiment is as follows:

[0029] Among them, R is C 2 h 5 、C 4 h 9 、C 6 h 13 、C 8 h 17 or

[0030] The 2-[(N-alkylcarbazolyl)vinyl]-1,8-naphthyridine derivatives of this embodiment can be used under the conditions of ordinary 8-watt 365nm and 6-watt 254nm low-energy ultraviolet wavelength irradiation conditions. Fluorescent phenomenon occurs, and the material has good thermal stability and photochemical stability. 2-[(N-Alkylcarbazolyl)vinyl]-1,8-naphthyridine derivatives can undergo two-photon absorption under 800nm ​​femtosecond laser, and can be excited to produce two-photon fluorescence effect. At the same time, 2-[(N-alkylcarbazolyl)vinyl]-1,8-naphthyridine derivatives have good solubility in common solvents (such as dichloromethane, chloroform, methanol, etc.), Therefore, it can have broad application prospects in many fields.

[...

specific Embodiment approach 2

[0032] Specific embodiment 2: The preparation method of 2-[(N-alkylcarbazolyl)vinyl]-1,8-naphthyridine derivatives in this embodiment is carried out according to the following steps:

[0033] 1. Weigh 1~2% of 2-methyl-1,8-naphthyridine, 1~2% of N-alkyl-3-formylcarbazole, 5~6% of ZnCl according to mass percentage 2 and 90~93% N,N-dimethylformamide, mix evenly, heat to 110°C~130°C, stir and react for 6~7h, cool to room temperature after the reaction, to obtain the reaction solution;

[0034] 2. Pour the reaction solution into 2 times the hydrochloric acid with a mass percentage of 20% by volume, let it stand overnight, filter, collect the filter cake and immerse it in water, and adjust its pH value to 7 with 30% ammonia water by mass percentage ~8, filter, collect the filter cake, and vacuum-dry for 2~3h at a temperature of 20°C~30°C, perform column chromatography on the dried product, collect the chromatographic liquid, and evaporate to dryness to obtain 2-[(N -Alkylcarbazolyl...

specific Embodiment approach 3

[0041] Specific embodiment three: the difference between this embodiment and specific embodiment two is: the 2-methyl-1,8-naphthyridine of 1.5% and the N-alkyl of 1.5% are weighed by mass percentage described in step one -3-Formylcarbazole, 5.5% ZnCl 2 and 91.5% N,N-dimethylformamide. Others are the same as in the second embodiment.

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Abstract

The invention relates to a 2-[(N- alkyl carbazolyl) vinyl]-1, 8-naphthyridine derivative as well as a preparation method and an application thereof, which relates to the 1,8-naphthyridine derivative and a preparation method and an application thereof, and solves the problems in the existing bi-photon absorption material that a molecular synthesis route of a large yoke system is long, the efficiency is low, the heat stability is poor and the photochemical stability is poor. The structural formula of the 2-[(N- alkyl carbazolyl) vinyl]-1, 8-naphthyridine derivative is as follows: the preparation method of the 2-[(N- alkyl carbazolyl) vinyl]-1, 8-naphthyridine derivative is characterized in that 2- methyl-1, 8-naphthyridine is linked with N-alkyl carbazole to have Knoevenagel reaction under the condition by adopting zinc chloride (ZnCl2) as condensing agent and dimethyl formamide (DMF) as solvent. The 2-[(N- alkyl carbazolyl) vinyl]-1, 8-naphthyridine derivative has strong fluorescent absorption performance and bi-photon absorption performance and good photochemical stability and heat stability. The 2-[(N- alkyl carbazolyl) vinyl]-1, 8-naphthyridine derivative is applied to the field of the laser three-dimensional micro machining and the conversion of bi-photon fluorescent.

Description

technical field [0001] The invention relates to 1,8-naphthyridine derivatives, a preparation method and application thereof. Background technique [0002] With the continuous deepening of the research on the two-photon absorption properties of materials, it is found that organic two-photon absorption materials are widely used in three-dimensional optical data storage due to their advantages of fast instantaneous response, high linear transmittance, strong three-dimensional processing ability, and high spatial resolution. Has been widely used. [0003] Since the two-photon absorption theory was first proposed in 1931, it was not confirmed experimentally until 30 years later. After years of research, organic two-photon absorption materials have been widely used. The molecules designed with high two-photon absorption mainly include the following Aspects: the molecule has a π-conjugated center and has a better rigid plane; increases the electron-donating ability of the electron...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C09K11/06
Inventor 张轶弛吴谊群贺春英陈志敏
Owner HEILONGJIANG UNIV
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