Squarylium cyanine dye and preparation method therefor

Abstract

The invention provides a squarylium cyanine dye and a preparation method therefor. The preparation method comprises the following steps: (1) firstly mixing a benzoindoles compound with squaric acid diethyl ester in an alcohol solvent, heating under the effect of triethylamine until reflux, reacting for 2-4 h, cooling, and carrying out suction filtration; (2) carrying out a reflux reaction on the product in the step 1) and malononitrile in the alcohol solvent under the effect of triethylamine, reacting for 10-30 min, washing with acetic acid, and carrying out suction filtration; and (3) heating the product in the step (2) and the benzoindoles compound with carboxyl in methylbenzene and n-butyl alcohol until reflux, and reacting for 7-10 h to obtain an end-product. The squarylium cyanine dye is relatively long in absorption and emission wavelength and good in light stability, active group carboxyl is introduced at the same time, and the squarylium cyanine dye can react with amino groups in biomolecules and is used for marking various biomolecules; and the synthetic method is simple, mild in condition and higher in yield, and provides good application prospects in the fields of molecular signature, fluorescence imaging and the like.

Description

technical field [0001] The invention belongs to the field of organic dye synthesis, in particular to a squarylium dye and a preparation method thereof. Background technique [0002] In 1856, Williamsf discovered cyanine dyes (also known as cyanines). Seventeen years later, Vogel discovered that such dyes had exceptionally sensitive photosensitivity. Since then, cyanine dyes have developed rapidly. Indocyanine dyes are an important branch of cyanine dyes. Due to its large molar extinction coefficient, good fluorescence performance, increased fluorescence efficiency after combining with the matrix, large tunable range of maximum absorption wavelength, easy synthesis and relatively high stability, it has been widely used in infrared laser dyes and optical storage materials in recent years. , Nucleic acid labeling and biomedical application research have been widely used. Many dyes currently used have shorter maximum absorption wavelength and fluorescence emission wavelength, a...

AI Technical Summary

Problems solved by technology

However, this type of dye has poor photostability, and the synthesis is relatively cumbersome and the yield is low. The preparation process of squaraine dyes includes the classic condensation method and microwave excitation synthesis method. Their devices are relatively complicated, the operation is relatively cumbersome, and the reaction conditions Harsh, low yield, and there are few squarylium dyes that can directly label biomolecules, and the current commercial near-infrared fluorescent labeling dyes are expensive

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