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A Visible Light-Driven Boron Concentrated Photochromic Material and Its Preparation and Application

A photochromic material and visible light technology, applied in the direction of color-changing fluorescent materials, chemical instruments and methods, compounds containing elements of group 3/13 of the periodic table, etc., can solve problems such as limiting the development of boron-heterocondensed ring systems, and achieve excellent results The effect of quantum yield and broad application prospect

Active Publication Date: 2022-05-24
HUNAN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the boron atom itself is extremely electrophilic, especially showing high sensitivity to air and water, which limits the development of boron heterofused ring systems to a certain extent.

Method used

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  • A Visible Light-Driven Boron Concentrated Photochromic Material and Its Preparation and Application
  • A Visible Light-Driven Boron Concentrated Photochromic Material and Its Preparation and Application
  • A Visible Light-Driven Boron Concentrated Photochromic Material and Its Preparation and Application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068]

[0069] Compound A (200 mg, 0.4 mmol) and anhydrous dichloromethane (50 mL) were added to a dry 100 mL one-neck flask, and after fully dissolving, it was cooled to 0°C. In the dark, N-bromosuccinimide (79.5 mg, 0.4 mmol) was added portionwise. The reaction was performed at room temperature in the dark for 4 h, and the reaction process was monitored by spot plate. After the reaction was completed, 2 mL of water was added to quench the reaction. It was then extracted with 50 mL of saturated brine and 50 mL of dichloromethane. Anhydrous Na for organic phase 2 SO 4 After drying, the solvent was removed by suction filtration. The residue was purified by flash column chromatography on silica gel (petroleum ether) to give 227 mg of yellow compound B in 98% yield.

[0070] The structure of the compound of formula B was confirmed by means of hydrogen NMR and carbon spectroscopy.

[0071] 1 H NMR (400MHz, CDCl 3 ): δ7.71(d,J=7.6Hz,2H),7.34(t,J=7.4Hz,2H),7.18(t,J=7.3Hz...

Embodiment 2

[0084] At room temperature, we have a 5×10 -5 The tetrahydrofuran solution of mol / L compound D was tested by ultraviolet absorption spectrum, and the results were as follows Figure 7 (A). Compound D at 382nm (ε=2.64×10 4 L mol -1 cm -1) appeared at a strong absorption peak, the absorption end extended to about 445nm, which can be excited by visible light. After exposure to visible light at ~400 nm, compound D undergoes a ring-closure reaction, and at 487 nm (ε=5.66×10 3 Lmol -1 cm -1 ) a new absorption band appears. With light exposure time, photosteady state was reached after 45 s. This process is also accompanied by a color change of the compound, and the solution turns from colorless to yellow. Under visible light (λ>450nm) illumination, the yellow solution returned to the original colorless solution. like Figure 7 As shown in (B), the tetrahydrofuran solution of compound D can be excited by alternating short-wave and long-wave, and can reciprocate more than te...

Embodiment 4

[0086] Fluorescence properties of compound D in tetrahydrofuran solution. The result is as Figure 8 As shown, an obvious fluorescence emission peak appeared at 446 nm, and with the prolongation of illumination, the fluorescence intensity there gradually weakened, and the photo-steady state was reached after 45 s. This may be due to the overlapping of the ultraviolet absorption spectrum and the fluorescence emission spectrum of the ring-closed isomer D, and there is an energy transfer (FRET) process, resulting in fluorescence quenching. The isolated pure ring-opening isomer D, the fluorescence quantum yield of its tetrahydrofuran solution is Φ F = 2.14% (with 0.5M quinoline sulfate as reference).

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Abstract

The invention belongs to the field of optoelectronic materials, and specifically discloses a visible light-driven photochromic material. The invention provides a compound with a new structure, and finds that the compound exhibits excellent reversible photochromism and excellent quantum yield, not only In this way, the molecule can exhibit good photochromic reaction characteristics without using high-energy ultraviolet light excitation. The material described in the invention has great application prospects in technical fields such as optical information storage, logic gates, anti-counterfeiting, and non-destructive data readout.

Description

technical field [0001] The invention relates to the field of organic photochromic materials, in particular to a visible light-driven boron-doped photochromic material. Background technique [0002] Visible light-driven photochromic switch molecules have attracted great attention for their potential applications in optoelectronic switching, bioimaging, and photopharmacology, mainly because visible light is less destructive and harmful to optical devices and biological cells. At present, visible-light-driven diarylethene molecular design usually extends the conjugated system of the aryl unit, reducing the HOMO-LUMO energy gap of the ring-opened isomer, making it absorb in the visible region. In 1997, Lehn et al. synthesized a class of visible light-driven diarylethenes for the first time. By introducing two thiophene rings at the 5- and 5'-positions of the thiophene ring, respectively, the absorption of open / closed ring isomers reached visible light region. The study found t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K9/02
CPCC07F5/025C09K9/02C09K2211/1092C09K2211/1096
Inventor 曾泽兵黄婷婷邦雅文谢胜王燕培
Owner HUNAN UNIV
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