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A kind of near-infrared metal complex and its preparation and application
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A metal complex, near-infrared technology, used in medical preparations containing active ingredients, compounds containing elements of Group 8/9/10/18 of the periodic table, pharmaceutical formulations, etc. problem, to achieve the effect of good chemical stability, easy industrial production and abundant raw materials
Active Publication Date: 2019-09-13
NANJING UNIV OF POSTS & TELECOMM
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[0005] Boron atoms are basically introduced into azadipyrromethene dyes to generate BODIP (Ehrenschwender, T.; Wagenknechet, H.A.J.Org.Chem., 2011,76(7):2301-2304), so far, few Researchers, introducing transition metals into dipyrromethene dyes
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Embodiment 1
[0050] This embodiment needs to prepare the metal complex of near-infrared absorption, in the above general formula, when R 1 N, N dimethylamino, R 2 is bromine, M is Pt, n is 1, C^N is When complex D1, its molecular formula is:
[0051]
[0052] Step S1: Preparation of dipyrromethene dye C1, namely N^N auxiliary ligand: the specific steps are:
[0053] (1): The preparation of unsaturated aryl ketone A1, wherein the molecular formula of unsaturated aryl ketone A1 is:
[0054]
[0055] Weigh p-bromoacetophenone (1000mg), dimethylaminobenzaldehyde (745mg), and KOH (84mg) into a single-necked bottle, add ethanol / water solution (85:15v / v 100mL) to the system, stir at room temperature, and react The time is about 12 hours. Treatment: suction filtration, ethanol recrystallization. 1 H NMR (400MHz, CDCl 3 ): δ=7.88(d, J=8.4Hz, 2H), 7.81(d, J=15.6Hz, 1H), 7.63(d, J=8.4Hz, 2H), 7.55(d, J=8.8Hz, 2H ), 7.26(d, J=15.6Hz, 1H), 6.70(d, J=8.8Hz, 2H), 3.05(s, 6H)ppm.
[0056] (2)...
Embodiment 2
[0068] The metal complex with near-infrared absorption that needs to be prepared in this embodiment is, when R 1 N, N dimethylamino, R 2 for When , M is Pt, n is 1, and C^N is When complex D2, its molecular formula is:
[0069]
[0070] Step S1: Preparation of dipyrromethene dye C2, i.e. N^N auxiliary ligand: the specific steps are:
[0071] First, the dipyrromethene dye C1 was prepared according to steps S1(1), (2)(3) in Example 1; then C2 was prepared according to the following step (4). The molecular formula of dipyrromethene dye C2 is:
[0072]
[0073] Step (4) prepares C2 by Suzuki reaction
[0074] a) Preparation of 9-propylcarbazole-3-boronate:
[0075] Weigh carbazole (1.67g, 10mmol) and tetrabutylammonium bromide (0.322g) into the reaction bottle, use an oil pump to evacuate-nitrogen-fill the vacuum cycle three times, protect the reaction system with nitrogen, and add two Methyl sulfoxide DMSO (40 mL) and 8.0 g 50% KOH were added dropwise to bromopropa...
Embodiment 3
[0085] Embodiment 3: the ultraviolet-visible spectrum test of C1 and D1:
[0086] The dilute solution (dichloromethane is solvent) of C1 and D1 two kinds of compounds in configuration embodiment 1, pipette 2mL complex solution in the fluorescence cuvette, then carry out ultraviolet-visible luminescent spectrum, as figure 1 , the test data show that: with the introduction of Pt complexes, a red shift is realized.
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Abstract
The invention belongs to the technical field of organic optoelectronic materials, and relates to a near-infrared metal complex and a preparation method and application thereof. The metal complex is prepared through the following steps of S1, preparation of a pyrrole dimethime dye C, namely, N^N auxiliary ligand; S2, preparation of a metal dichloro bridge; S3, preparation of the near-infrared metal complex, wherein the pyrrole dimethime dye and the metal dichloro bridge are subjected to a coordination reaction to obtain the near-infrared metal complex. The preparation method of the near-infrared metal complex is simple in process and rich in raw material, and industrial production is convenient. The metal complex can be used for the technical fields of photoacoustic imaging, photo-thermal therapy, biological marking and detecting and the like. Metal is introduced into a polyaza pyrrole dimethime compound, and therefore the metal complex with near-infrared absorption performance and good photo-thermal and chemical stability is obtained. The metal complex has the structural general formula shown as the following formula (please see the formula in the specification).
Description
technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and specifically relates to a near-infrared metal complex, a preparation method of the complex, and applications thereof in the fields of photoacoustic imaging, photothermal therapy, biomarking and detection, and the like. Background technique [0002] Near-infrared fluorescent dyes are a kind of functional dyes. Because of their good absorption in the near-infrared region, near-infrared technology is widely used in solar cells, tumor treatment, radio frequency identification systems, and anti-counterfeiting printing. [0003] Azadipyrromethene dyes are a new class of near-infrared fluorescent dyes that have received widespread attention in recent years. This type of dye has long absorption and emission wavelengths, good photostability, narrow half-peak width, high quantum yield, and large molar extinction coefficient. And other characteristics, because azadipyrromethene f...
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