Direct evidence of charge separation in a metal–organic framework: efficient and selective photocatalytic oxidative coupling of amines via charge and energy transfer
The selective aerobic oxidative coupling of amines under mild conditions is an important laboratory and commercial procedure yet a great challenge. In this work, a porphyrinic metal–organic framework, PCN-222, was employed to catalyze the reaction. Upon visible light irradiation, the semiconductor-l...
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| Published in | Chemical science (Cambridge) Vol. 9; no. 12; pp. 3152 - 3158 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
Royal Society of Chemistry
2018
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| Subjects | |
| Online Access | Get full text |
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| Abstract | The selective aerobic oxidative coupling of amines under mild conditions is an important laboratory and commercial procedure yet a great challenge. In this work, a porphyrinic metal–organic framework, PCN-222, was employed to catalyze the reaction. Upon visible light irradiation, the semiconductor-like behavior of PCN-222 initiates charge separation, evidently generating oxygen-centered active sites in Zr-oxo clusters indicated by enhanced porphyrin π-cation radical signals. The photogenerated electrons and holes further activate oxygen and amines, respectively, to give the corresponding redox products, both of which have been detected for the first time. The porphyrin motifs generate singlet oxygen based on energy transfer to further promote the reaction. As a result, PCN-222 exhibits excellent photocatalytic activity, selectivity and recyclability, far superior to its organic counterpart, for the reaction under ambient conditions
via
combined energy and charge transfer. |
|---|---|
| AbstractList | The selective aerobic oxidative coupling of amines under mild conditions is an important laboratory and commercial procedure yet a great challenge. In this work, a porphyrinic metal-organic framework, PCN-222, was employed to catalyze the reaction. Upon visible light irradiation, the semiconductor-like behavior of PCN-222 initiates charge separation, evidently generating oxygen-centered active sites in Zr-oxo clusters indicated by enhanced porphyrin π-cation radical signals. The photogenerated electrons and holes further activate oxygen and amines, respectively, to give the corresponding redox products, both of which have been detected for the first time. The porphyrin motifs generate singlet oxygen based on energy transfer to further promote the reaction. As a result, PCN-222 exhibits excellent photocatalytic activity, selectivity and recyclability, far superior to its organic counterpart, for the reaction under ambient conditions via combined energy and charge transfer.The selective aerobic oxidative coupling of amines under mild conditions is an important laboratory and commercial procedure yet a great challenge. In this work, a porphyrinic metal-organic framework, PCN-222, was employed to catalyze the reaction. Upon visible light irradiation, the semiconductor-like behavior of PCN-222 initiates charge separation, evidently generating oxygen-centered active sites in Zr-oxo clusters indicated by enhanced porphyrin π-cation radical signals. The photogenerated electrons and holes further activate oxygen and amines, respectively, to give the corresponding redox products, both of which have been detected for the first time. The porphyrin motifs generate singlet oxygen based on energy transfer to further promote the reaction. As a result, PCN-222 exhibits excellent photocatalytic activity, selectivity and recyclability, far superior to its organic counterpart, for the reaction under ambient conditions via combined energy and charge transfer. The selective aerobic oxidative coupling of amines under mild conditions is an important laboratory and commercial procedure yet a great challenge. In this work, a porphyrinic metal-organic framework, PCN-222, was employed to catalyze the reaction. Upon visible light irradiation, the semiconductor-like behavior of PCN-222 initiates charge separation, evidently generating oxygen-centered active sites in Zr-oxo clusters indicated by enhanced porphyrin π-cation radical signals. The photogenerated electrons and holes further activate oxygen and amines, respectively, to give the corresponding redox products, both of which have been detected for the first time. The porphyrin motifs generate singlet oxygen based on energy transfer to further promote the reaction. As a result, PCN-222 exhibits excellent photocatalytic activity, selectivity and recyclability, far superior to its organic counterpart, for the reaction under ambient conditions combined energy and charge transfer. The selective aerobic oxidative coupling of amines under mild conditions is an important laboratory and commercial procedure yet a great challenge. In this work, a porphyrinic metal–organic framework, PCN-222, was employed to catalyze the reaction. Upon visible light irradiation, the semiconductor-like behavior of PCN-222 initiates charge separation, evidently generating oxygen-centered active sites in Zr-oxo clusters indicated by enhanced porphyrin π-cation radical signals. The photogenerated electrons and holes further activate oxygen and amines, respectively, to give the corresponding redox products, both of which have been detected for the first time. The porphyrin motifs generate singlet oxygen based on energy transfer to further promote the reaction. As a result, PCN-222 exhibits excellent photocatalytic activity, selectivity and recyclability, far superior to its organic counterpart, for the reaction under ambient conditions via combined energy and charge transfer. The selective aerobic oxidative coupling of amines under mild conditions is an important laboratory and commercial procedure yet a great challenge. In this work, a porphyrinic metal–organic framework, PCN-222, was employed to catalyze the reaction. Upon visible light irradiation, the semiconductor-like behavior of PCN-222 initiates charge separation, evidently generating oxygen-centered active sites in Zr-oxo clusters indicated by enhanced porphyrin π-cation radical signals. The photogenerated electrons and holes further activate oxygen and amines, respectively, to give the corresponding redox products, both of which have been detected for the first time. The porphyrin motifs generate singlet oxygen based on energy transfer to further promote the reaction. As a result, PCN-222 exhibits excellent photocatalytic activity, selectivity and recyclability, far superior to its organic counterpart, for the reaction under ambient conditions via combined energy and charge transfer. For the first time, the photoexcited charge separation in a metal–organic framework has been evidenced with clear ESR signals, based on efficient and selective photocatalytic oxidative coupling of amines. The selective aerobic oxidative coupling of amines under mild conditions is an important laboratory and commercial procedure yet a great challenge. In this work, a porphyrinic metal–organic framework, PCN-222, was employed to catalyze the reaction. Upon visible light irradiation, the semiconductor-like behavior of PCN-222 initiates charge separation, evidently generating oxygen-centered active sites in Zr-oxo clusters indicated by enhanced porphyrin π-cation radical signals. The photogenerated electrons and holes further activate oxygen and amines, respectively, to give the corresponding redox products, both of which have been detected for the first time. The porphyrin motifs generate singlet oxygen based on energy transfer to further promote the reaction. As a result, PCN-222 exhibits excellent photocatalytic activity, selectivity and recyclability, far superior to its organic counterpart, for the reaction under ambient conditions via combined energy and charge transfer. |
| Author | Liu, Hang Jiang, Hai-Long Su, Ji-Hu Xu, Caiyun Li, Dandan |
| AuthorAffiliation | a Hefei National Laboratory for Physical Sciences at the Microscale , CAS Key Laboratory of Soft Matter Chemistry , Collaborative Innovation Center of Suzhou Nano Science and Technology , Department of Chemistry , University of Science and Technology of China , Hefei , Anhui 230026 , P. R. China . Email: jianglab@ustc.edu.cn ; http://staff.ustc.edu.cn/∼jianglab b CAS Key Laboratory of Microscale Magnetic Resonance , Synergetic Innovation Center of Quantum Information and Quantum Physics , Department of Modern Physics , University of Science and Technology of China , Hefei 230026 , P. R. China |
| AuthorAffiliation_xml | – name: b CAS Key Laboratory of Microscale Magnetic Resonance , Synergetic Innovation Center of Quantum Information and Quantum Physics , Department of Modern Physics , University of Science and Technology of China , Hefei 230026 , P. R. China – name: a Hefei National Laboratory for Physical Sciences at the Microscale , CAS Key Laboratory of Soft Matter Chemistry , Collaborative Innovation Center of Suzhou Nano Science and Technology , Department of Chemistry , University of Science and Technology of China , Hefei , Anhui 230026 , P. R. China . Email: jianglab@ustc.edu.cn ; http://staff.ustc.edu.cn/∼jianglab |
| Author_xml | – sequence: 1 givenname: Caiyun surname: Xu fullname: Xu, Caiyun organization: Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Soft Matter Chemistry, Collaborative Innovation Center of Suzhou Nano Science and Technology, Department of Chemistry, University of Science and Technology of China – sequence: 2 givenname: Hang surname: Liu fullname: Liu, Hang organization: Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Soft Matter Chemistry, Collaborative Innovation Center of Suzhou Nano Science and Technology, Department of Chemistry, University of Science and Technology of China – sequence: 3 givenname: Dandan surname: Li fullname: Li, Dandan organization: Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Soft Matter Chemistry, Collaborative Innovation Center of Suzhou Nano Science and Technology, Department of Chemistry, University of Science and Technology of China – sequence: 4 givenname: Ji-Hu surname: Su fullname: Su, Ji-Hu organization: CAS Key Laboratory of Microscale Magnetic Resonance, Synergetic Innovation Center of Quantum Information and Quantum Physics, Department of Modern Physics, University of Science and Technology of China, Hefei 230026 – sequence: 5 givenname: Hai-Long orcidid: 0000-0002-2975-7977 surname: Jiang fullname: Jiang, Hai-Long organization: Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Soft Matter Chemistry, Collaborative Innovation Center of Suzhou Nano Science and Technology, Department of Chemistry, University of Science and Technology of China |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/29732097$$D View this record in MEDLINE/PubMed |
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| Snippet | The selective aerobic oxidative coupling of amines under mild conditions is an important laboratory and commercial procedure yet a great challenge. In this... For the first time, the photoexcited charge separation in a metal–organic framework has been evidenced with clear ESR signals, based on efficient and selective... |
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| SubjectTerms | Amines Catalytic activity Charge transfer Chemistry Coupling Energy transfer Light irradiation Photocatalysis Recyclability Separation Singlet oxygen Zirconium |
| Title | Direct evidence of charge separation in a metal–organic framework: efficient and selective photocatalytic oxidative coupling of amines via charge and energy transfer |
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