Porous Crystalline Olefin-Linked Covalent Organic Frameworks
The first unsubstituted olefin-linked covalent organic framework, termed COF-701, was made by linking 2,4,6-trimethyl-1,3,5-triazine (TMT) and 4,4′-biphenyldicarbaldehyde (BPDA) through Aldol condensation. Formation of the unsubstituted olefin (-CHCH-) linkage upon reticulation is confirmed by Four...
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| Published in | Journal of the American Chemical Society Vol. 141; no. 17; pp. 6848 - 6852 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
01.05.2019
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| Subjects | |
| Online Access | Get full text |
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| Abstract | The first unsubstituted olefin-linked covalent organic framework, termed COF-701, was made by linking 2,4,6-trimethyl-1,3,5-triazine (TMT) and 4,4′-biphenyldicarbaldehyde (BPDA) through Aldol condensation. Formation of the unsubstituted olefin (-CHCH-) linkage upon reticulation is confirmed by Fourier transform infrared (FT-IR) spectroscopy and solid-state 13C cross-polarization magic angle spinning (CP-MAS) NMR spectroscopy of the framework and of its 13C-isotope-labeled analogue. COF-701 is found to be porous (1715 m2 g–1) and to retain its composition and crystallinity under both strongly acidic and basic conditions. The high chemical robustness is attributed to the unsubstituted olefin linkages. Immobilization of the strong Lewis acid BF3·OEt2 in the pores of the structure yields BF3⊂COF-701. In the material, the catalytic activity of the guest is retained, as evidenced in a benchmark Diels–Alder reaction. |
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| AbstractList | The first unsubstituted olefin-linked covalent organic framework, termed COF-701, was made by linking 2,4,6-trimethyl-1,3,5-triazine (TMT) and 4,4'-biphenyldicarbaldehyde (BPDA) through Aldol condensation. Formation of the unsubstituted olefin (-CH═CH-) linkage upon reticulation is confirmed by Fourier transform infrared (FT-IR) spectroscopy and solid-state
C cross-polarization magic angle spinning (CP-MAS) NMR spectroscopy of the framework and of its
C-isotope-labeled analogue. COF-701 is found to be porous (1715 m
g
) and to retain its composition and crystallinity under both strongly acidic and basic conditions. The high chemical robustness is attributed to the unsubstituted olefin linkages. Immobilization of the strong Lewis acid BF
·OEt
in the pores of the structure yields BF
⊂COF-701. In the material, the catalytic activity of the guest is retained, as evidenced in a benchmark Diels-Alder reaction. The first unsubstituted olefin-linked covalent organic framework, termed COF-701, was made by linking 2,4,6-trimethyl-1,3,5-triazine (TMT) and 4,4'-biphenyldicarbaldehyde (BPDA) through Aldol condensation. Formation of the unsubstituted olefin (-CH═CH-) linkage upon reticulation is confirmed by Fourier transform infrared (FT-IR) spectroscopy and solid-state 13C cross-polarization magic angle spinning (CP-MAS) NMR spectroscopy of the framework and of its 13C-isotope-labeled analogue. COF-701 is found to be porous (1715 m2 g-1) and to retain its composition and crystallinity under both strongly acidic and basic conditions. The high chemical robustness is attributed to the unsubstituted olefin linkages. Immobilization of the strong Lewis acid BF3·OEt2 in the pores of the structure yields BF3⊂COF-701. In the material, the catalytic activity of the guest is retained, as evidenced in a benchmark Diels-Alder reaction.The first unsubstituted olefin-linked covalent organic framework, termed COF-701, was made by linking 2,4,6-trimethyl-1,3,5-triazine (TMT) and 4,4'-biphenyldicarbaldehyde (BPDA) through Aldol condensation. Formation of the unsubstituted olefin (-CH═CH-) linkage upon reticulation is confirmed by Fourier transform infrared (FT-IR) spectroscopy and solid-state 13C cross-polarization magic angle spinning (CP-MAS) NMR spectroscopy of the framework and of its 13C-isotope-labeled analogue. COF-701 is found to be porous (1715 m2 g-1) and to retain its composition and crystallinity under both strongly acidic and basic conditions. The high chemical robustness is attributed to the unsubstituted olefin linkages. Immobilization of the strong Lewis acid BF3·OEt2 in the pores of the structure yields BF3⊂COF-701. In the material, the catalytic activity of the guest is retained, as evidenced in a benchmark Diels-Alder reaction. The first unsubstituted olefin-linked covalent organic framework, termed COF-701, was made by linking 2,4,6-trimethyl-1,3,5-triazine (TMT) and 4,4′-biphenyldicarbaldehyde (BPDA) through Aldol condensation. Formation of the unsubstituted olefin (-CHCH-) linkage upon reticulation is confirmed by Fourier transform infrared (FT-IR) spectroscopy and solid-state 13C cross-polarization magic angle spinning (CP-MAS) NMR spectroscopy of the framework and of its 13C-isotope-labeled analogue. COF-701 is found to be porous (1715 m2 g–1) and to retain its composition and crystallinity under both strongly acidic and basic conditions. The high chemical robustness is attributed to the unsubstituted olefin linkages. Immobilization of the strong Lewis acid BF3·OEt2 in the pores of the structure yields BF3⊂COF-701. In the material, the catalytic activity of the guest is retained, as evidenced in a benchmark Diels–Alder reaction. The first unsubstituted olefin-linked covalent organic framework, termed COF-701, was made by linking 2,4,6-trimethyl-1,3,5-triazine (TMT) and 4,4′-biphenyldicarbaldehyde (BPDA) through Aldol condensation. Formation of the unsubstituted olefin (-CH═CH-) linkage upon reticulation is confirmed by Fourier transform infrared (FT-IR) spectroscopy and solid-state ¹³C cross-polarization magic angle spinning (CP-MAS) NMR spectroscopy of the framework and of its ¹³C-isotope-labeled analogue. COF-701 is found to be porous (1715 m² g–¹) and to retain its composition and crystallinity under both strongly acidic and basic conditions. The high chemical robustness is attributed to the unsubstituted olefin linkages. Immobilization of the strong Lewis acid BF₃·OEt₂ in the pores of the structure yields BF₃⊂COF-701. In the material, the catalytic activity of the guest is retained, as evidenced in a benchmark Diels–Alder reaction. |
| Author | Yaghi, Omar M Zhu, Chenhui Diercks, Christian S Lyu, Hao |
| AuthorAffiliation | Department of Chemistry UC Berkeley-KACST Joint Center of Excellence for Nanomaterials for Clean Energy Applications Advanced Light Source King Abdulaziz City for Science and Technology |
| AuthorAffiliation_xml | – name: UC Berkeley-KACST Joint Center of Excellence for Nanomaterials for Clean Energy Applications – name: Advanced Light Source – name: Department of Chemistry – name: King Abdulaziz City for Science and Technology |
| Author_xml | – sequence: 1 givenname: Hao orcidid: 0000-0001-7393-2456 surname: Lyu fullname: Lyu, Hao organization: Department of Chemistry – sequence: 2 givenname: Christian S orcidid: 0000-0002-7813-0302 surname: Diercks fullname: Diercks, Christian S organization: Department of Chemistry – sequence: 3 givenname: Chenhui surname: Zhu fullname: Zhu, Chenhui organization: Advanced Light Source – sequence: 4 givenname: Omar M orcidid: 0000-0002-5611-3325 surname: Yaghi fullname: Yaghi, Omar M email: yaghi@berkeley.edu organization: King Abdulaziz City for Science and Technology |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31017397$$D View this record in MEDLINE/PubMed |
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