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Near-infrared absorption phosphorescent material based on Ir(ttp)-aza-BODIPY, preparation method and application thereof

A technology of heterofluoroboron dipyrrole and tetramethyl porphyrin is applied in the field of near-infrared absorbing phosphorescent materials, which can solve the problems of short luminescence life and achieve the effect of long phosphorescence decay life.

Inactive Publication Date: 2015-11-11
NANJING UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of compound has a strong molar absorptivity in the near-infrared region, but its luminescence lifetime is short

Method used

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  • Near-infrared absorption phosphorescent material based on Ir(ttp)-aza-BODIPY, preparation method and application thereof
  • Near-infrared absorption phosphorescent material based on Ir(ttp)-aza-BODIPY, preparation method and application thereof
  • Near-infrared absorption phosphorescent material based on Ir(ttp)-aza-BODIPY, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The synthesis of embodiment 1. compound A:

[0026] Carbonyl chloride·tetracresyliridium porphyrin Ir(ttp)(CO)Cl (15.8mg, 0.017mmol), brominated azafluoroboron dipyrrole aza-BODIPY-a (13.7mg, 0.021mmol) were added to the reactor ) (12.3mg, 0.019mmol), K 2 CO 3 (47.0mg, 0.34mmol) and 1.0mL of benzene, the reaction mixture was refrigerated and degassed three times, and reacted at 150°C for 72 hours under the protection of nitrogen. After the reaction is finished, the solvent is spin-dried under reduced pressure, and the 2 Cl 2 / Hexane (1:1) as a developing agent for silica gel column chromatography (100-140 mesh, Qingdao Ocean Chemical Factory) to obtain 11.4mg of compound B. Yield: 46%.R f =0.64(CH 2 Cl 2 / hexane=1:1). 1 HNMR (400MHz,C 6 D. 6 ):δ1.27(d,2H,J=8.3Hz),2.41(s,12H),5.48(s,1H),5.83(d,2H,J=8.7Hz),6.28(s,1H),6.91 (d, 3H, J=7.9Hz), 7.02-7.08(m, 5H), 7.23(d, 4H, J=7.4Hz), 7.35(d, 4H, J=7.3Hz), 7.41-7.47(m, 4H), 7.72(d, 2H, J=7.5Hz), 7.93(d, 4H, J=7.4Hz),...

Embodiment 2

[0027] Embodiment 2. Synthesis of compound B:

[0028] Add carbonyl chloride·tetracresyl iridium porphyrin Ir(ttp)(CO)Cl (18.0mg, 0.019mmol), bromoazafluoroboron dipyrrole aza-BODIPY-b (13.7mg, 0.021mmol) into the reactor ), K 2 CO 3 (53.9mg, 0.39mmol) and 1.0mL of benzene, the reaction mixture was refrigerated and degassed three times, and reacted at 150°C for 48 hours under the protection of nitrogen. After the reaction is finished, the solvent is spin-dried under reduced pressure, and the 2 Cl 2 / Hexane (1:1) as a developing agent for silica gel column chromatography (100-140 mesh, Qingdao Ocean Chemical Factory) separation, to obtain 17.1 mg of compound A. Yield: 61%.R f =0.68(CH 2 Cl 2 / hexane=1:1). 1 HNMR (400MHz,C 6 D. 6 ):δ1.12(d,2H,J=8.4Hz),2.42(s,12H),5.40(d,2H,J=4.3Hz),5.55(s,1H),6.35(s,3H),6.86 -7.05(m,4H),7.26-7.31(m,6H),7.38-7.43(m,6H),7.69(d,2H,J=5.8Hz),7.91(d,2H,J=7.7Hz), 8.01(d, 4H, J=7.6Hz), 8.22(d, 4H, J=7.6Hz), 8.97(s, 8H).; HRMS(FABMS): Calcdfor...

Embodiment 3

[0029] Example 3. Application

[0030] We tested the stability of the target compound by using ultraviolet spectroscopy, using methylene blue as a reference, using the efficiency value of a 671nm laser singlet oxygen, and a monochromatic laser with a wavelength of 690nm as a light source. The experimental results show that the synthesized target compound has good stability and high singlet oxygen generation efficiency, and can be successfully applied to photodynamic therapy. We carried out the MTTassay test of photosensitizer A in HeLa cells in the presence of light and in the absence of light to detect its cytotoxicity. The experimental results show that under the condition of no light source, with the increase of the photosensitizer concentration, the activity of the cells basically does not change and maintains at about 100%. The results show that the cells do not die in the dark in the presence of the photosensitizer. In contrast, under the irradiation of 690nm laser ligh...

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Abstract

A series of near-infrared compounds based on iridium-porphyrin / aza-BODIPY are represented as the following structural formulas. Compared with the prior art, the invention is characterized in that the Ir(ttp)-aza-BODIPY compound is synthesized through an Ir-C bond axial connection method for the first time, wherein the compounds has the optical properties of both a transition metal iridium and the aza-BODIPY. On one hand, because of the unique d6 electron configuration of the central metal Ir(III), the compound has a quite effective intersystem crossing coefficient, thereby generating long-life phosphorescence emission and singlet oxygen, and on the other hand, the aza-BODIPY have very strong absorption in the near-infrared zone, so that the absorption wavelength of the compound can be red-shifted into the near-infrared zone, so that the material can be more widely applied. The invention also discloses the preparation method of the material.

Description

technical field [0001] The invention relates to a near-infrared absorbing phosphorescent material, in particular to an iridium tetraphenylporphyrin-azafluoroboron dipyrrole {Ir(ttp)-aza-BODIPY} near-infrared absorbing phosphorescent material and its preparation method and application. Background technique [0002] Near-infrared absorbing fluorescent dyes have become a research hotspot in recent years due to their unique properties, and have been widely used in various fields. In the near-infrared region, biological tissue absorption and scattering are minimal, [see: (a) Aubin, J.E. biothchnol., 2001, 19, 316-317.] Therefore, it can greatly improve the tissue penetration ability of photons, avoid the influence of autofluorescence interference, and reduce the light damage to organisms. [Refer to: (a) Wu, X.M., et al. cyanine hybrid nanocomposite for bioimaging in vivo: a breakthrough in photo-stability and bright fluorescence with large Stokesshift. Chem. Sci., 2013, 4, 1221...

Claims

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Application Information

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IPC IPC(8): C07F15/00C07F5/02C09K11/06A61K41/00A61K49/00A61P35/00
CPCA61K41/00A61K49/00C09K11/06C07F5/022C07F15/0033C09K2211/185C09K2211/1029C09K2211/1007
Inventor 沈珍陈建成周金风盖立志
Owner NANJING UNIV
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