CN-117209452-B - Difluoro benzothiadiazole full-color fluorescent molecule, preparation and application thereof

Abstract

The invention discloses a difluoro benzothiadiazole full-color fluorescent molecule, and preparation and application thereof. The structural formula of the difluoro benzothiadiazole fluorescent molecule is shown as formula (1): In formula (1), R is independently selected from the group consisting of silane groups, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups. The difluoro benzothiadiazole fluorescent molecule provided by the invention has novel structure, is a compound with higher fluorescence intensity and longer quantum yield and service life, and can realize fluorescence emission in the whole visible range from blue to red in liquid state, solid state and film state.

Inventors

• WANG CHAOYANG
• CHEN SIHONG

Assignees

• 华南师范大学

Dates

Publication Date

20260505

Application Date

20230811

Claims (6)

1. 1. A difluoro benzothiadiazole fluorescent molecule, wherein the difluoro benzothiadiazole fluorescent molecule is selected from the group consisting of compounds of the following structures: 、 、 、 、 、 、 、 、 、 。
2. 2. The method for preparing the difluoro benzothiadiazole fluorescent molecule according to claim 1, which is characterized by comprising the following steps of reacting 4, 7-dibromo-5, 6-difluoro benzo [ c ] [1,2,5] thiadiazole with terminal alkyne to prepare the difluoro benzothiadiazole fluorescent molecule, wherein the terminal alkyne is selected from 1-hexyne, 2-acetylene thiophene, benzene alkyne, 4-tolylene, 4-ethynyl anisole, p-chloroacetylene, 1-ethynyl naphthalene, 4-ethynyl biphenyl, 9- (4-ethynyl phenyl) carbazole and 4-ethynyl triphenylamine.
3. 3. The method for preparing the difluoro benzothiadiazole fluorescent molecule according to claim 2, wherein the reaction comprises adding a catalyst to participate in the reaction, and the catalyst comprises a palladium catalyst and a copper (I) salt.
4. 4. The method for preparing the difluoro benzothiadiazole fluorescent molecule according to claim 2, wherein the molar ratio of 4, 7-dibromo-5, 6-difluoro benzo [ c ] [1,2,5] thiadiazole to terminal alkyne is 1 (2-4).
5. 5. The method for producing a fluorescent molecule of the difluorobenzothiadiazole type according to any one of claims 2 to 4, wherein said reaction is carried out at 110 to 130 ℃ for 20 to 40 hours.
6. 6. Use of a fluorescent molecule of the difluoro benzothiadiazole type as claimed in claim 1 for preparing organic luminescent materials, fluorescent dyes or fluorescent probes.

Description

Difluoro benzothiadiazole full-color fluorescent molecule, preparation and application thereof Technical Field The invention belongs to the field of fluorescent materials, and particularly relates to a difluoro benzothiadiazole full-color fluorescent molecule, and preparation and application thereof. Background Panchromatic fluorescent molecules refer to the polarity of a compound that can fluoresce throughout the visible range. Their diverse emission characteristics make them have a wide application potential in the fields of chemical sensing, cell imaging, and organic photoelectric materials, etc. Therefore, the development of full-color fluorescent small molecules with simple structure, wide emission range and various fluorescent properties has important significance. Full color fluorescent materials reported in literature and patents for a long time mainly comprise the following: (1) Quantum dots are nanocrystals (inorganic nanocrystals) with a size in the range of 2-50 nm. The light emitting range of the quantum dots is controlled/regulated by controlling the particle size, surface chemistry, distribution and constituent materials of the quantum dots. For example, quantum dots of small size exhibit blue light, while quantum dots of larger size exhibit red light. Nanomaterial from 1-100nm also showed similar variation. (2) Carbon dots are zero-dimensional carbon nanomaterials with diameters of 2-10nm, and have tunable photoluminescence performance. The carbon dots prepared by different carbon sources or different synthesis methods have different emission behaviors, and the emission of the carbon dots is regulated and controlled by changing the structure, physical state and morphology of the carbon dots. (3) Panchromatic organic small molecules refer to a class of donor-acceptor (D-A) organic compounds with chromophores. Typically, their emission is fluorescence modulated by substituents that modulate different electron donating or withdrawing properties of the acceptor or donor core. The traditional cadmium/lead-containing quantum dots, rare earth nano materials and emerging carbon dots have the advantages of good light stability, high quantum yield and the like. They also suffer from some fatal drawbacks. For example, poor reproducibility, unknown light emission mechanism and structure-activity, which greatly limit their application as full-color luminescent materials in various fields. The full-color organic small molecules are becoming a hot spot method for constructing full-color fluorescent materials because of the remarkable advantages of clear luminescence mechanism, clear structure-activity relationship, various luminescence properties and the like. However, the current full-color fluorescent molecules still have the defects of few available core frameworks, narrow luminous range and the like, and ideal full-color fluorescent molecules are still very deficient. Therefore, development of novel full-color fluorescent molecules, research of their structure-activity relationship, and expansion of their application in the field of fluorescence detection remain significant. The full-color fluorescent small molecule has the advantages of small volume, flexible structural modification and the like, so that the fluorescent material emitted in the whole visible light range has strong dependence on organic small molecule compounds. At present, the common construction strategies of full-color fluorescent micromolecules mainly comprise the steps of selecting an acceptor core, simultaneously introducing different electron donors (D) at two ends of an acceptor (A) to construct a D-A-D type molecule, selecting a donor core, introducing different electron donors (D) at one end of a donor, and introducing different electron acceptors (A) at the other end of the donor to construct the D-D-A type molecule. Both methods allow easy construction of molecules with different intensities of Intramolecular Charge Transfer (ICT) effects, which increase leads to a red shift in wavelength in the absorption and emission spectra. For example, sun group disclosed in document doi.org/10.1002/chem.202203797 that 8 types of D-D-A type full-color aggregation-induced emission molecules were designed with carbazole as a core. The Yasuda subject group discloses that 5D-A-D full-color thermal delay fluorescent materials are synthesized by taking phthalonitrile or dicyanopyrazine as an acceptor core and coupling different donors in the literature doi.org/10.1002/adfm.20151206. In summary, full-color fluorescent molecules are often used in the fields of fluorescence sensing, cell imaging, etc. because of their wide and diverse emission characteristics, there is a strong demand for new full-color fluorescent molecules with better performance in various fluorescent material fields. However, the full-color fluorescent molecules reported so far still have the defects of narrow emission range, single fluorescent property and the like. Disclos