Axial chirality-based binaphthol-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene complex and preparation method thereof

Abstract

The invention discloses an axial chirality-based binaphthol-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene complex and a preparation method thereof. The preparation method comprises the following steps: adding binaphthol into a first solvent, adding sodium carbonate and iodomethane, and performing a reaction so as to obtain 2,2'-dimethoxy-1,1'-binaphthalene; adding the 2,2'-dimethoxy-1,1'-binaphthalene into a second solvent, adding n-butyllithium and N,N-dimethyl formamide at -78 DEG C to 0 DEG C, increasing the temperature to room temperature, and performing a reaction so as to obtain 2,2'-dimethoxy-[1,1'-binaphthalene]-carboxaldehyde; adding the 2,2'-dimethoxy-[1,1'-binaphthalene]-carboxaldehyde into a third solvent, adding 2,4-dimethylpyrrole and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, and performing a stirring reaction; and adding triethylamine and a boron trifluoride diethyl etherate solution, and performing a reaction continuously for 5-10 hours, so as to obtain the desired complex. Through simple synthesis steps, the axial chirality-based binaphthol-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene complex is prepared, the preparation cost is low, the reaction condition is mild, purification is easy, and the synthesized compound has both an axial chirality structure of binaphthol and a fluorescence characteristic of a 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene complex.

Description

technical field [0001] The invention relates to an axial chiral binaphthol-fluoroboron dipyrrole complex and a preparation method thereof, belonging to the technical field of organic functional luminescent materials. Background technique [0002] Circularly polarized luminescence (CPL) has been favored by researchers due to its potential applications in 3D optical displays, organic light-emitting diodes (OLEDs), CPL lasers, and biological probes and imaging. So far, the compounds with CPL activity mainly focus on chiral metal complexes, organic helicene polymers and nanometer self-assembled materials. [0003] Recently, circularly polarized luminescent active small organic molecules (CPL-SOMs) have been generally accepted due to their advantages of facile synthesis, easy modification and tunable emission wavelength. However, the following challenges still exist in the field of research on CPL-SOMs: 1) The luminescence asymmetry factor (g lum ) is relatively small, usually ...

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Problems solved by technology

However, the following challenges still exist in the field of research on CPL-SOMs: 1) The luminescence asymmetry factor (g lum ) is relatively small, usually in the range of 10 -5 –10 -3 ; 2) There are few reports of CPL active compounds showing high quantum yields in solution and solid state at the same time, which is not only due to the weak luminescent nature of most fluorophores, but also the effect of aggregation-induced luminescence quenching (ACQ); 3 ) to obtain optically pure CPL-SOMs usually requires complex synthetic steps and costly chiral resolution procedures

These unfavorable factors severely limit the practical application of CPL-SOMs

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