Macrocyclic polyamine-based polyacetylene fluorescent sensor and preparation method thereof

Abstract

The invention discloses a macrocyclic polyamine-based polyacetylene fluorescent sensor and a preparation method thereof. The preparation method comprises three steps of preparation of polyacetylene monomer, preparation of polyacetylene macromolecule and post functionalization of the macromolecule. A Sonogashira reaction is carried out on phenylacetylene and 1-(4-bromine butoxy)-4-iodobenzene so as to obtain 1-(4-bromine butoxy)-4-(phenyl acetenyl) benzene, an addition reaction is carried out on the 1-(4-bromine butoxy)-4-(phenyl acetenyl) benzene under the catalytic actions of tungsten hexachloride and tetraphenyltin so as to obtain a polyacetylene macromolecule P1 free of post functionalization, and a substitution reaction is carried out on the polyacetylene macromolecule P1 and the macrocyclic polyamine cyclen so as to obtain a post-functionalized polyacetylene macromolecule P2, and the polyacetylene macromolecule P2 is the polyacetylene fluorescent sensor. A fluorescence titration result shows that the disubstituted polyacetylene macromolecule P2 can recognize Cu<2+> with high selectivity and high sensitivity, and also can detect S<2-> indirectly. The invention provides a simple method for synthesizing the disubstituted polyacetylene fluorescent sensor.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a macrocyclic polyamine-based polyacetylene fluorescence sensor and a preparation method thereof. Background technique [0002] In recent years, conjugated polymers have been widely used in the field of materials, involving molecular wires, light-emitting diodes, optical limiting materials, field effect transistors, and fluorescent sensors. In sensor research, conjugated polymer fluorescence sensors have more excellent properties than other fluorescent molecules. For example, the "molecular wire effect" of conjugated polymers can enhance the charge transport capability within the molecule, making the conjugated polymer fluorescent The sensitivity of the sensor is greatly increased. So far, there are many types of conjugated polymer fluorescent sensors reported, which are used to detect various substances, including metal ions, anions, organic small molecules, biomolecules, and so ...

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Problems solved by technology

[0003] Disubstituted polyacetylene has good light, thermal stability and luminescent properties, which meet the necessary conditions for fluorescence sensors, but there are relatively few studies on polyacetylene in fluorescence sensors.

The reason may be that conjugated polymer fluorescent sensors usually contain polar acceptor groups (such as bipyridine, terpyridine, quinoline, etc.), and double-substituted polymers with polar groups are synthesized by direct polymerization. Acetylene is very difficult, which directly affects the application of polyacetylene in the field of sensors

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