Phenylvinyl-BODIPY derivative and preparation method thereof

A technology of phenylvinyl and derivatives, which is applied in the field of organic materials, can solve the problems of insufficient research on the synthesis methodology of phenylvinyl BODIPY, and achieve favorable ion complexation and biological dyeing, convenient synthesis, and high molar light absorption The effect of the coefficient

CN107903282AInactive Publication Date: 2018-04-13HUANGHE S & T COLLEGE
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Publication Date
2018-04-13
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention provides a phenylvinyl-BODIPY derivative, the structure of which is as follows: shown in the specification, wherein R1 is alkoxy, Br, boric acid ester, N,N-dimethylamino or diphenylaminegroup, and R is H, 4-bromophenyl / 4-iodobiphenyl or ethyl propionate. Specifically, ten new compounds are provided, and are convenient to synthesize and easy to prepare and purify. The phenylvinyl-BODIPY derivative has extremely high molar absorption coefficient and wide ultraviolet-visible absorption spectrum, and has a wide application prospect on solar batteries and biological detection.
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Description

technical field

[0001] The invention belongs to the field of organic materials related to solar cells and biological fluorescence analysis technology, in particular to a class of phenylvinyl-BODIPY derivatives and a preparation method thereof. Background technique

[0002] Due to its unique properties, BODIPY (fluoroboron dipyrrole) has attracted widespread attention. This type of molecule has high fluorescence quantum yield, low toxicity and excellent stability, so that they are widely used in ion detection, bioluminescence calibration and solar cells and other fields. In addition, fluoroborate dipyrrole can also be conveniently synthesized and modified by organic synthesis. However, the absorption wavelength range of the BODIPY module matrix is ​​narrow, the maximum absorption is only about 500nm, and the fluorescence emission wavelength is about 510nm. Such a spectral structure is not conducive to the application in the field of energy conversion, and the color is monoto...

Examples

Embodiment

[0045] Preparation of Compound 1-10

[0046] 1. The general synthetic method of compound 1-10 (unless otherwise specified)

[0047] Add 0.1 mmol (or 0.2 mmol) of the corresponding BODIPY and 0.35 equivalent of aromatic aldehyde to a microwave tube, dissolve the substrate with 2ML (or 4ML) dry DMF, then catalyst: 50 μL (or 100 μL) piperidine and 50 μL (or 100 μL) acetic acid was added to the reaction mixture. Using Biotage microwave reactor, react at 130°C for 10-45Min. The solvent was then rotovapped using an oil pump as a vacuum source. Finally, the target compound is purified by column chromatography or thin layer chromatography.

[0048]

[0049] image 3 Structure and Yield of Compound 1-10

[0050]Two, the specific synthetic steps, reaction rate and yield of compound 1-10

[0051] Compound 1: BODIPY A 0.1 mmol was reacted with 4-N,N-dimethylaminobenzaldehyde for 45 Min to obtain 46.5 mg of Compound 1, yield: 65.3%. 1 H NMR (CDCl 3 ,400MHz)δ7.84(2H,d,J=8.3Hz,Ar-...