A kind of linear π-extended xanthene dye and its preparation method
A xanthene and linear technology, which is applied in the field of molecular fluorescent dye preparation, can solve the problems of short absorption and emission wavelengths, and achieve the effects of increased conjugation, easy promotion and use, and low risk factor
Inactive Publication Date: 2019-10-18
TIANJIN UNIVERSITY OF TECHNOLOGY
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[0004] Xanthene dyes have the advantages of large molar absorptivity, high fluorescence quantum yield, good photostability, and good biocompatibility, and are often used as reference substances for measuring quantum efficiency. Therefore, in order to expand the application of xanthene dyes in organisms, it is necessary to expand the wavelength of the dye to make its wavelength in the deep red or near-infrared region
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[0026] A linear π-extended xanthene dye whose emission wavelength is in the deep red and near-infrared regions, and whose general structure is as follows:
[0027]
[0028] The preparation method of the linear π-extended xanthene fluorescent dye 1 fused with the benzoxazine and xanthene, the preparation process is as follows:
[0029]
[0030] Concrete preparation steps are as follows:
[0031] 1) Synthesis of Intermediate 7
[0032] In a 100mL round bottom flask, add 3.746g (23.77mmol), o-chloronitrobenzene 5, 2.517g, (20.3mmol) p-methoxyphenol 6 and 2.646g (24.9mmol) acid-binding agent Na 2 CO 3 , add 25mL dry DMF as solvent, pass N 2 Protection, reaction at 100 ° C for 14h. After the reaction was completed, it was poured into a mixed solution containing 30mL of dichloromethane and 100mL of ice water, extracted 3 times with 30mL of dichloromethane, and after the combined organic phase was dried, the target product was separated and purified by column chromatography...
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The invention provides linear type Pi-expanded xanthene dyes. The linear type Pi-expanded xanthene dyes have emission wavelength located in deep-infrared and near-infrared regions and have a general structural formula as described in the specification. In the general structural formula, Ar is selected from the group consisting of a benzene ring, a pyridine ring, a quinoline ring and a naphthalenering; R is selected from the group consisting of H, a methoxy group, an amino group, a cyano group and a trifluoromethyl group; and R' is selected from the group consisting of a methyl group and an ethyl group. The preparation method for one linear type Pi-expanded xanthene dye comprises the following steps: pre-assembling an aromatic ring with an amino group at an ortho position to the C-6 position of a xanthene dye, and then allowing the amino group on the aromatic ring to nucleophilically substitute a hydrogen atom at the C-7 position of xanthene to form a C-N bond so as to synthesize the linear type Pi-expanded xanthene fluorescent dye. The invention has the following advantages: a series of the dyes prepared by using the method provided by the invention have good membrane permeabilityand can be used for cell imaging; and the preparation method is simple and convenient, does not need high temperature and high pressure in the preparation process, does not use extremely flammable and explosive chemicals, has low danger coefficient, needs no expensive metal for a catalytic reaction, and is easy to promote and use.
Description
technical field [0001] The invention relates to the preparation of molecular fluorescent dyes in optical sensing imaging detection technology, in particular to a linear π-extended xanthene dye and a preparation method thereof. Background technique [0002] In recent years, fluorescence imaging has become a powerful technique for non-invasive monitoring of objects and physiological activities due to its high temporal and spatial resolution. Therefore, fluorescence imaging has great application value in different fields such as biology, clinical diagnosis, and drug discovery. Fluorescent probes have become an important tool in bioimaging technology because of their advantages of high sensitivity and easy operation. However, due to the diversity of the properties of fluorescent probes, different probes have different properties. Not all fluorescent probes can be applied to biological imaging. Fluorescent dyes suitable for biological detection should have the following basic el...
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IPC IPC(8): C09B57/00C09K11/06C07D498/04G01N21/64
Inventor 曾宪顺王庆
Owner TIANJIN UNIVERSITY OF TECHNOLOGY