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Fluorescent compounds with wide color tunability and aggregation-induced emission characteristics
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A fluorescent compound and compound technology, applied in cyanide, organic chemistry, inorganic chemistry, etc., can solve the problem of inability to adjust the emission at will
Pending Publication Date: 2021-10-12
THE HONG KONG UNIV OF SCI & TECH
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Although many conventional AIE emitters have been constructed based on different structural motifs, including tetraphenylethylene, hexaphenylsilyl, tetraphenylpyrazine, and distyrylanthracene, the emission of these AIE systems cannot be tuned at will to Provides emission of individual colors in the visible and even near-infrared (NIR) region
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Embodiment 1
[0208] Synthesis of TTV
[0209] Bromide-substituted triphenylaminemoiety (1.2 mmol), thiophen-2-ylboronic acid moiety (1 mmol), THF (20 mL), K 2 CO 3 Aqueous solution (2M, 1.6mL) and Pd(PPh 3 ) 4 (0.05mmol) mixture was degassed and filled with N 2 . The mixture was refluxed overnight. The reaction was quenched by adding water (30 mL), and washed with CH 2 Cl 2 (3 x 30 mL) extraction. The combined organic layers were washed with anhydrous Na 2 SO 4 Dry and evaporate the solvent. The residue was purified by silica gelcolumn chromatography using petroleumether to give the desired product TTV in 78% yield.
[0210] Compound TTV: 1 H NMR (400MHz, CD 2 Cl 2 ): 7.60 (d, J = 6.8Hz, 2H), 7.41 (d, J = 8Hz, 2H), 7.37-7.33 (m, 4H), 7.13-7.06 (m, 9H). 13 C NMR (100MHz, CDCl 3 ): 147.49, 147.20, 144.26, 129.27, 128.54, 127.95, 126.71, 124.42, 123.98, 123.75, 123.02, 122.21. ESI HRMS: For C 22 h 17 NS[M] + Calculated: 327.1082, Found: 327.1066.
Embodiment 2
[0212] Synthesis of TTG
[0213] TTG was synthesized according to Scheme 3. The synthesis process of TTG is similar to that of TTV, except that the raw materials are different.
[0214] Compound TTG: 1 H NMR (400MHz, CDCl 3 ): 9.85(s, 1H), 7.70(d, J=4Hz, 1H), 7.52(d, J=8.8Hz, 2H), 7.31-7.28(m, 5H), 7.14-7.05(m, 8H). 13 C NMR (100MHz, CDCl 3): 182.57, 154.55, 149.11, 146.94, 141.28, 137.70, 129.46, 127.22, 126.10, 125.14, 123.85, 122.83, 122.33. ESI HRMS: For C 23 h 17 NOS[M] + Calculated: 355.1031, Found: 355.1030.
Embodiment 3
[0216] Synthesis of TTY
[0217] TTY was synthesized according to Scheme 3. The synthesis process of TTY is similar to that of TTV, except that the raw materials are different.
[0218] Compound TTY: 1 H NMR (400MHz, CDCl 3 ):9.83(s,1H),7.69(d,J=4Hz,1H),7.46(d,J=9.2Hz,2H),7.25(d,J=4.8Hz,1H),7.10-7.08(m, 4H), 6.91-6.85 (m, 6H), 3.81 (s, 6H). 13 CNMR (100MHz, CDCl 3 ): 182.47, 156.51, 155.06, 149.98, 140.78, 139.85, 137.79, 127.19, 127.11, 124.21, 122.27, 119.23, 114.85, 55.46. ESI HRMS: For C 25 h 21 NO 3 S[M] + Calculated: 415.1242, Found: 415.1248.
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Abstract
The present subject matter relates to fluorescent compounds that have aggregation-induced emission (AIE) characteristics and tunable emission colors. The emission range of these compounds covers the whole visible region and extends to the near infrared (NIR) area. The compounds can be utilized as bio-probes for lipid droplet (LD) -specific imaging with excellent image contrast to the cell background. Additionally, the high brightness and homology of these compounds endow them with excellent performance for visualizing cell fusion. Further, upon exposure to white lightirradiation, the compounds can generate reactive oxygen species (ROS) with high efficiency. Therefore, the compounds can be effective in photodynamic ablation of cancer cells.
Description
[0001] cross reference [0002] This application claims priority to Provisional U.S. Patent Application No. 62 / 918,110, filed January 16, 2019, filed by the present inventors and incorporated herein by reference in its entirety. technical field [0003] The present subject matter generally relates to a series of fluorescent compounds with aggregation-induced luminescence characteristics and their applications in bioimaging and phototherapeutics. Background technique [0004] The exploration of fluorescent materials and technologies has opened up new avenues for scientific progress, social development, and public health. Research related to fluorescence has even been recognized with a Nobel Prize in recent years. Fluorescent biomaterials offer researchers a powerful platform for analytical sensing and optical imaging, and have demonstrated fluorescent Biomaterials are extremely useful for biological visualization, clinical diagnosis, and disease treatment. Although many ty...
Claims
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