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Two-Step, One-Pot Synthesis of Visible-Light-Responsive 6-Azopurines.

ABSTRACT: The first general two-step, one-pot synthetic route to 6-azopurines is presented. Microwave-assisted nucleophilic aromatic substitution of protected 6-chloropurines with hydrazines or hydrazides, followed by metal-free oxidation with oxygen, gives 6-azopurines in high to excellent yields. Photophysical studies revealed intensive n-?* absorption band that makes trans-to-cis photoswitching possible using visible light (? = 530 nm).

SUBMITTER: Kolarski D

PROVIDER: S-EPMC5633830 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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Two-Step, One-Pot Synthesis of Visible-Light-Responsive 6-Azopurines.

Kolarski Dušan D Szymanski Wiktor W Feringa Ben L BL

Organic letters 20170911 19

The first general two-step, one-pot synthetic route to 6-azopurines is presented. Microwave-assisted nucleophilic aromatic substitution of protected 6-chloropurines with hydrazines or hydrazides, followed by metal-free oxidation with oxygen, gives 6-azopurines in high to excellent yields. Photophysical studies revealed intensive n-π* absorption band that makes trans-to-cis photoswitching possible using visible light (λ = 530 nm). ...[more]

PMID: 28891651

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Project description:A magnesium-based metal-organic framework (Mg-MOF-74) exhibits excellent CO2 adsorption under ambient conditions. However, the photostability of Mg-MOF-74 for CO2 adsorption is poor. In this study, Mg x Cu1-x -MOF-74 was synthesized by using a facile "one-pot" method. Furthermore, the effects of synthesis conditions on the CO2 adsorption capacity were investigated comprehensively. X-ray diffraction, Fourier transform infrared, scanning electron microscopy, thermo gravimetric analysis, inductively coupled plasma atomic emission spectroscopy, ultraviolet-visible spectroscopy and photoluminescence spectroscopy, and CO2 static adsorption-desorption techniques were used to characterize the structures, morphology, and physicochemical properties of Mg x Cu1-x -MOF-74. CO2 uptake of Mg x Cu1-x -MOF-74 under visible light illumination was measured by the CO2 static adsorption test combined with the Xe lamp. The results revealed that Mg x Cu1-x -MOF-74 exhibited excellent photocatalytic activity. Furthermore, the CO2 adsorption capacity of Mg x Cu1-x -MOF-74 was excellent at a synthesis temperature and time of 398 K and 24 h in dimethylformamide (DMF)-EtOH-MeOH mixing solvents, respectively. Mg x Cu1-x -MOF-74 retained a crystal structure similar to that of the corresponding monometallic MOF-74, and its CO2 uptake under visible light was superior to that of the corresponding monometallic MOF-74. Particularly, the CO2 uptake of Mg0.4Cu0.6-MOF-74 under Xe lamp illumination for 24 h was the highest, up to 3.52 mmol·g-1, which was 1.18 and 2.09 times higher than that of Mg- and Cu-MOF-74, respectively. The yield of the photocatalytic reduction of CO2 to CO was 49.44 μmol·gcat -1 over Mg0.4Cu0.6-MOF-74 under visible light for 8 h. Mg2+ and Cu2+ functioned as open alkali metal that could adsorb and activate CO2. The synergistic effect between Mg and Cu metal strengthened Mg x Cu1-x -MOF-74 photostability for CO2 adsorption and broadened the scope of its photocatalytic application. The "bimetallic" strategy exhibits considerable potential for use in MOF-based semiconductor composites and provides a feasible method for catalyst design with remarkable CO2 adsorption capacity and photocatalytic activity.

Dataset Information

Two-Step, One-Pot Synthesis of Visible-Light-Responsive 6-Azopurines.

Publications

Two-Step, One-Pot Synthesis of Visible-Light-Responsive 6-Azopurines.

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