Fluorenyl-carborane photoelectric material as well as preparation method and application thereof
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A technology of optoelectronic materials, carborane, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc.
Inactive Publication Date: 2020-09-18
NANJING UNIV OF POSTS & TELECOMM
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However, it has not been effectively applied in the field of room temperature phosphorescence and circularly polarized luminescence
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[0033] The preparation method of the fluorenyl-carborane photoelectric material of the present invention comprises the following steps:
[0034] Synthesis of o-A
[0035] Step 1: Anaerobic, anhydrous and protected from light, under the condition of 50-70°C, 9,9-dibutane-2-bromo-7-iodofluorene and aromatic terminal alkyne are dissolved in triethylamine solution, and stirred to react 4- 12h to obtain the intermediate compound A-R, the synthetic route is shown in the following formula:
[0036]
[0037] Step 2: at room temperature, decaborane (B 10 h 14 ) into the toluene solution dropwise, heated to 90-120°C, refluxed for 2-4h, cooled to 20-50°C, then added intermediate compound A-R, and the temperature rose to 90-120°C Reflux for 2-12h to prepare the target compound o-A. The synthetic route is shown in the following formula:
[0038]
Embodiment approach
[0040] The present invention designs and synthesizes a fluorenyl-carborane photoelectric material with an asymmetric central structure type, and the aryl R-substituted functional group of the carborane is any one of benzene, benzocarbazole, triphenylamine, naphthalene, anthracene, pyrene, etc. .
[0041] 1. The specific implementation method is as follows:
[0042] Preparation of o-A1:
[0043] The synthetic route is as follows:
[0044]
[0045] Step 1: Weigh 9,9-dibutane-2-bromo-7-iodofluorene (6.00g, 12.42mmol), an appropriate amount of 5% copper iodide CuI catalyst, and tetrakistriphenylphosphine palladium catalyst to avoid light Under the protection of nitrogen, add it to a 250mL double-necked round bottom flask, vacuumize and change the nitrogen at least three times, and add the anhydrous and oxygen-free triethylamine (Et 3 N) 60mL, add phenylacetylene (1.50mL, 13.66mmol, 0.93g / mL) dropwise under the condition of heating and stirring in an oil bath, raise the tempe...
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Abstract
The invention discloses a fluorenyl-carborane photoelectric material as well as a preparation method and application thereof. The fluorenyl-carborane photoelectric material is a carborane organic photoelectric material based on intramolecular charge transfer intelligent regulation and control and has a fluorenyl-carborane conjugated asymmetric o-A structure. The general formula of the chemical structure of the material is shown in the specification, the main structure skeleton of the material is donor-acceptor configuration, fluorenyl is an electron donor, o-carborane is an electron acceptor,and the photoluminescence behavior of the material is accurately adjusted by virtue of molecular charge transfer. Under the stimulation of external conditions, the material has multiple light-emittingbehaviors comprising aggregation-induced emission, crystallization-induced emission, circular polarization emission and room-temperature phosphorescence, which are related to the asymmetric donor-acceptor conformation. The material has a wide application prospect in the fields of information storage, 3D display, anti-counterfeiting marks, 3D glasses, induction, biological imaging, light emittingdevices and the like.
Description
technical field [0001] The invention relates to a fluorenyl-carborane photoelectric material and a preparation method thereof, and relates to the field of synthesis and preparation of organic photoelectric materials. Background technique [0002] Boron clusters, such as icosahedral closed carboranes (i.e., meta, para, ortho carboranes), composed of boron atoms, have been studied for more than half a century. Due to their unique electronic properties and excellent (thermal and chemical) stability, they have proven to be versatile building blocks in organometallic chemistry, medicine, catalysis, and more. In addition, the σ-aromaticity of the three-dimensional boron cage can be smoothly adapted to the two-dimensional π-system, which has been used to develop new fluorescent materials, phosphorescent materials and thermally activated delayed fluorescence (TADF) materials. Furthermore, the electron-withdrawing properties of carboranes with rigid cage structures can give rise to ...
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