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Near-infrared absorbing phosphorescent material based on rhodium tetraphenylporphyrin-azafluoroboron dipyrrole and its preparation method and application

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

Inactive Publication Date: 2017-03-08
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 absorbing phosphorescent material based on rhodium tetraphenylporphyrin-azafluoroboron dipyrrole and its preparation method and application
  • Near-infrared absorbing phosphorescent material based on rhodium tetraphenylporphyrin-azafluoroboron dipyrrole and its preparation method and application
  • Near-infrared absorbing phosphorescent material based on rhodium tetraphenylporphyrin-azafluoroboron dipyrrole and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The synthesis of embodiment 1. compound A:

[0028] Add rhodium tetraphenyl porphyrin chloride Rh (ttp) Cl (15.8 mg, 0.019 mmol), bromo azafluoro boron dipyrrole aza-BODIPY-a (13.7 mg, 0.021 mmol) in 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 28 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) developer was separated by silica gel column chromatography to obtain 17.1 mg of compound A. Yield: 61%.R f =0.61 (CH 2 Cl 2 / hexane=1:1). 1 H NMR (400MHz, CDCl 3 ):δ0.44(d,J=8.5Hz,2H),2.69(s,12H),5.45(d,J=8.4Hz,2H),5.98(s,1H),6.75(s,1H),7.30 -7.36(m,6H),7.45(d,J=8.0Hz,2H),7.51-7.52(m,9H),7.56-7.63(m,3H),7.80(d,J=3.3Hz,2H), 8.04(d, J=7.7Hz, 4H), 8.09(d, J=7.8Hz, 4H), 8.87(s, 8H).; HRMS(FABMS): Calcd for [C 80 h 56 BBrF 2 RhN 7 ] + ([M] + ): m / z 1347.2903. Fou...

Embodiment 2

[0029] Embodiment 2. Synthesis of compound B:

[0030] Add rhodium tetraphenylporphyrin chloride Rh (ttp) Cl (15.8 mg, 0.019 mmol), bromo azafluoro boron dipyrrole aza-BODIPY-b (13.7 mg, 0.021 mmol) in 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 30 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) developer was separated by silica gel column chromatography to obtain 11.4 mg of compound B. Yield: 66%.R f =0.57(CH 2 Cl 2 / hexane=1:1). 1 H NMR (400MHz, CDCl 3 ):δ0.52(d,J=8.6Hz,2H),2.71(s,12H),5.57(d,J=9.0Hz,2H),6.22(s,1H),6.71(s,1H),7.25 -7.30(m,3H),7.48(d,J=7.8Hz,2H),7.51-7.58(m,9H),7.60-7.67(m,6H),7.82(d,J=7.2Hz,2H), 8.06(d, J=7.6Hz, 8H), 8.83(s, 8H).HRMS(FABMS): Calcd for [C 80 h 56 BBrF 2 RhN 7 ] + ([M] + ):m / z1347.2903.Found:m / z.1347.2908.

[0031] Its U...

Embodiment 3

[0032] Embodiment 3. Synthesis of compound C:

[0033] Add rhodium tetraphenylporphyrin chloride Rh (ttp) Cl (15.8mg, 0.019mmol), bromoazine fluoroboron dipyrrole aza-BODIPY-c (13.7mg, 0.021mmol), 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 32 hours under the protection of nitrogen. After the reaction is finished, the solvent is spin-dried under reduced pressure, and the 2 Cl 2 The developer of / hexane (1:1) was separated by silica gel column chromatography to obtain 6.74 mg of compound B. Yield: 39%. 1 HNMR (400MHz, CDCl 3 ):δ0.40(d,J=8.4Hz,1H),0.44(s,1H),2.67(s,12H),5.00(t,J 1 =4.0Hz,J 2 =7.8Hz,1H),5.51(s,1H),6.33(d,J=7.4Hz,1H),6.69(s,1H),6.88(t,J 1 =7.8Hz,J 2 =7.8Hz,1H),7.17(d,J=7.8Hz,1H),7.37-7.39(m,8H),7.47-7.50(m,2H),7.53-7.55(m,5H),7.71(s, 1H), 7.81-7.82(m, 4H), 7.84(d, J=8.0Hz, 4H), 7.99(d, J=7.4Hz, 4H), 8.08(s, 8H).HRMS(FABMS): Calcd for [C 80 h 56 BBrF 2 RhN 7...

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Abstract

Rhodium tetraphenylporphyrin-aza-BODIPY-based near infrared compounds have a structure shown in the specification. Compared with the prior art, a preparation method of the compounds is characterized in that Rhodium tetraphenylporphyrin-aza-BODIPY compounds {Rh(ttp)-aza-BODIPY} compounds are synthesized in a Rh-C bond axial connection mode. The compounds simultaneously have the optical properties of a transition metal rhodium and aza-BODIPY. The center metal Rh<III> has a unique d<6> electron configuration, so the compounds have a very effective intersystem crossing coefficient, and generate long life phosphorescent light and singlet oxygen. The aza-BODIPY has very strong absorption in the near infrared region, and can successfully shift the absorption wavelength of the compounds into the near infrared region to make the compounds widely applied. The invention also discloses the preparation method of the compounds.

Description

technical field [0001] The invention relates to a near-infrared absorbing phosphorescent material, in particular to a rhodium tetraphenylporphyrin-azafluoroboron dipyrrole {Rh(ttp)-aza-BODIPY} near-infrared absorbing phosphorescent material and its preparation method and use. 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, [cf.: (a) Aubin, J.E. Autofluorescence of viable cultured mammalian cells. J. Histochem. Cytochem., 1979, 27, 36–43.12. (b) Weisleder, R.A clearer vision for in vivo imaging. Nat. biothchnol., 2001, 19, 316-317.] Therefore, it can greatly improve the tissue penetration ability of photons and avoid the influence of autofluorescence interference, reducing the light damage to organisms. [See: (a) Wu, X.M., etal. In vivo and in si...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06A61K41/00A61P35/00
CPCA61K41/0076C07F5/022C09K11/06C09K2211/1029C09K2211/104
Inventor 沈珍陈建成周金风盖立志
Owner NANJING UNIV
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