Macrocyclic extended porphyrin compound containing carbazole unit and preparation method thereof

A technology of porphyrin compound and carbazole unit, applied in macrocyclic extended porphyrin compound and its synthesis, extended porphyrin and its preparation field, can solve the problems such as few reports of meso-position unsubstituted extended porphyrin and the like, and achieve excellent Solubility, easy control, effect of simple purification method

Active Publication Date: 2020-06-09
SHANGHAI UNIV
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  • Abstract
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Problems solved by technology

[0003] For the study of macrocyclic extended porphyrin chemistry, although important progress has been made, most of the extended porphyrin compounds reported in the literature are extended porphyrins substituted at the meso-position, and relatively unsubstituted extended porphyrins reported at the meso-position less

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  • Macrocyclic extended porphyrin compound containing carbazole unit and preparation method thereof
  • Macrocyclic extended porphyrin compound containing carbazole unit and preparation method thereof
  • Macrocyclic extended porphyrin compound containing carbazole unit and preparation method thereof

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Embodiment 1

[0068] In this embodiment, a macrocyclic extended porphyrin compound containing a carbazole unit has a chemical structure of the general formula 1,

[0069]

[0070] . Its synthetic route is as follows:

[0071]

[0072] see Figure 1-10 and Figure 21 . Synthesis of intermediate 1-2

[0073]

[0074] Add compound Ⅰ-1 (2.0g, 6.2mmol), bis-pinacol boroester (3.6g, 14.3mmol), potassium acetate (3.1g, 31.0mmol) and 1,1' - Bisdiphenylphosphinoferrocenepalladium dichloride (226.0 mg, 0.3 mmol). Vacuum and replace with argon protection. Add 60 mL of 1,4-dioxane with a syringe, and place it in an oil bath at 95°C for 24 hours to react. Stop the reaction, spin off the solvent under reduced pressure, dissolve the residue in 120 mL of ethyl acetate, wash the organic phase with water, wash with saturated brine, dry over anhydrous sodium sulfate, and filter. The organic phase was spin-off, and the residue was separated by silica gel column chromatography using petroleum e...

Embodiment 2

[0085] This embodiment is basically the same as Embodiment 1, especially in that:

[0086] In this embodiment, a macrocyclic extended porphyrin compound containing a carbazole unit has a chemical structure of the general formula 2,

[0087]

[0088] . Its synthetic route is as follows:

[0089]

[0090] Synthesis of intermediate 2-2

[0091]

[0092] Add compound Ⅰ-1 (5.8g, 15.2mmol), bis-pinacol boroester (8.9g, 35.0mmol), potassium acetate (7.5g, 76.5mmol) and 1,1' - Bisdiphenylphosphinoferrocenepalladium dichloride (556.0 mg, 0.7 mmol). Vacuum and replace with argon protection. Add 120 mL of 1,4-dioxane with a syringe, and place it in an oil bath at 95°C for 24 hours to react. Stop the reaction, spin off the solvent under reduced pressure, dissolve the residue in 300 mL ethyl acetate, wash the organic phase with water, wash with saturated brine, dry over anhydrous sodium sulfate, and filter. The organic phase was spin-off, and the residue was separated by sil...

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Abstract

The invention discloses macrocyclic extended porphyrin containing a carbazole unit and a preparation method of the macrocyclic extended porphyrin. The extended porphyrin is a member of the isoporphyrin family, and the skeleton of the extended porphyrin is generally composed of more than 4 conjugated pyrrole rings / heterocycles. Compared with a traditional porphyrin structure, the macrocyclic extended porphyrin has more coordination atoms, a larger cavity and rich conformations. The extended porphyrin can be complexed with larger metal ions or form a host-guest complex with multiple transition metal ions, so that the extended porphyrin has excellent coordination ability. Meanwhile, because of a larger pi-electron conjugate path of the expanded porphyrin, the expanded porphyrin can show different topological aromaticity and excellent photoelectric and magnetic properties. The macrocyclic extended porphyrin synthesis method is simple, the raw materials are cheap and easy to obtain, the reaction is easy to control, and efficient and large-scale preparation can be realized. The expanded porphyrin supramolecular host has potential application value in the fields of organic catalysis, lifescience, material science, environmental energy and the like.

Description

technical field [0001] The invention relates to an extended porphyrin compound and a preparation method thereof, in particular to a macrocyclic extended porphyrin compound and a synthesis method thereof, which is applied in the technical field of isoporphyrin compound chemistry. Background technique [0002] Extended porphyrins belong to a large family of isoporphyrins. About 40 years ago, Woodward et al. first reported the construction of extended porphyrins based on the total synthesis of vitamin B12. Different from the porphyrin parent, the conjugated ring system of the macrocyclic extended porphyrin consists of more than 18 π electrons, has a larger cavity structure and a variety of π-conjugated configurations. In recent years, based on the synthesis of a series of macrocyclic extended porphyrins, the excellent photophysical, electrochemical and coordination properties of extended porphyrins have been reported successively. As an important class of supramolecular hosts, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22
CPCC07D487/22Y02E10/549
Inventor 雷川虎周伟男郝梦娣
Owner SHANGHAI UNIV
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