Photoactive Donor–Acceptor Covalent Organic Framework Material for Synergistic Cyclization Approach to Imidazole Derivatives
Xiaoman Sun
College of Chemistry, Jilin University, Changchun, P. R. China
Contribution: Investigation, Methodology, Formal analysis, Writing - original draft
Search for more papers by this authorQing Su
College of Chemistry, Jilin University, Changchun, P. R. China
Contribution: Data curation, Validation, Funding acquisition, Writing - review & editing
Search for more papers by this authorKexin Luo
College of Chemistry, Jilin University, Changchun, P. R. China
Contribution: Investigation, Validation, Formal analysis
Search for more papers by this authorShufang Liu
College of Chemistry, Jilin University, Changchun, P. R. China
Contribution: Software, Methodology, Visualization, Writing - original draft
Search for more papers by this authorHao Ren
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Jilin University, Changchun, P. R. China
Contribution: Conceptualization, Software
Search for more papers by this authorCorresponding Author
Qiaolin Wu
College of Chemistry, Jilin University, Changchun, P. R. China
Correspondence:
Qiaolin Wu ([email protected])
Contribution: Conceptualization, Supervision, Visualization, Funding acquisition, Writing - review & editing
Search for more papers by this authorXiaoman Sun
College of Chemistry, Jilin University, Changchun, P. R. China
Contribution: Investigation, Methodology, Formal analysis, Writing - original draft
Search for more papers by this authorQing Su
College of Chemistry, Jilin University, Changchun, P. R. China
Contribution: Data curation, Validation, Funding acquisition, Writing - review & editing
Search for more papers by this authorKexin Luo
College of Chemistry, Jilin University, Changchun, P. R. China
Contribution: Investigation, Validation, Formal analysis
Search for more papers by this authorShufang Liu
College of Chemistry, Jilin University, Changchun, P. R. China
Contribution: Software, Methodology, Visualization, Writing - original draft
Search for more papers by this authorHao Ren
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Jilin University, Changchun, P. R. China
Contribution: Conceptualization, Software
Search for more papers by this authorCorresponding Author
Qiaolin Wu
College of Chemistry, Jilin University, Changchun, P. R. China
Correspondence:
Qiaolin Wu ([email protected])
Contribution: Conceptualization, Supervision, Visualization, Funding acquisition, Writing - review & editing
Search for more papers by this authorFunding: This work was supported by the National Natural Science Foundation of China (No. 51703076)
ABSTRACT
As one of the most potential platforms for heterogeneous catalysis, two-dimensional porphyrin-based covalent organic frameworks (COFs) have attracted great research interests. In this work, following the correlation of COF structure and their performance, a type of donor–acceptor 2D COF (Por-COF-Zn) based on porphyrin and thiophene units was designed and easily constructed by one-pot method using 5,10,15,20-tetra-(4-aminophenyl)porphyrin (TAPP), thieno[3,2-b]thiophene-2,5-dicarbaldehyde, and zinc acetate. The as-synthesized COF material is tested to show high crystallinity and good thermal and chemical stability. The Brunauer–Emmett–Teller (BET) measure results show that the specific surface area of Por-COF-Zn is 413.6 m2g−1, and the pore volume is 0.279 cm3g−1. Transient photocurrent response and EIS measurement also demonstrate that Por-COF-Zn exhibits an efficient separation of photogenerated electron/hole pairs. The photocatalytic performance of the resulted COF was further evaluated by using intramolecular cyclization of N-phenyl-o-phenylenediamine and benzaldehyde to form benzimidazole derivative. The catalyst system exhibited good to high conversion efficiency, moderate substrate applicability, and excellent stability and recyclability for the catalytic cyclization approach of benzimidazoles. The catalytic mechanism should be contributed to the synergistic effect of organic framework and metallic zinc. Our current work also provides valuable information for understanding COF-based photocatalytic systems and further highlight new insights to meet new challenges of heterogeneous photocatalysis.
Conflicts of Interest
The authors declare no conflicts of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the Supporting Information of this article.
Supporting Information
| Filename | Description |
|---|---|
| aoc7671-sup-0001-Supporting_Information.docxWord 2007 document , 3.2 MB |
Figure S1. The SEM of Por-COF-Zn. Figure S2. The TEM of Por-COF-Zn. Figure S3. TGA of Por-COF-Zn. Figure S4. PXRD patterns of Por–COF–Zn before (black) and after treatments by 12 M HCl (red), 9 M NaOH (Cyan), methanol (blue) and THF (green). Figure S5. FT-IR spectra of Por–COF–Zn before (black) and after treatments by 12 M HCl (red), 9 M NaOH (Cyan), methanol (blue) and THF (green). Figure S6. XPS survey scan of Por-COF-Zn. Figure S7. The PXRD pattern of Por–COF–Zn after 10 catalytic cycles. Figure S8. The FT-IR spectra of Por–COF–Zn before (black) and after (red) 10 catalytic cycles. Figure S9. The PXRD pattern of Por–COF. Figure S10. The FT-IR spectra of Por–COF–Zn (blue) and Por-COF (red). 1H NMR data for benzimidazole derivatives. 1H NMR spectra. References. |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
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