Porous organic polymers (POPs), owing to their abundant porosity, high stability and well-tunable properties, are promising candidates as heterogeneous photocatalysts for organic transformations. Here we report two vinylene-bridged donor-acceptor (D-A) structural POPs (TpTc-POP and TbTc-POP) that are facilely constructed by the electron-rich triarylamine and electron-deficient tricyanomesitylene as key building blocks by the organic base catalyzed Knoevenagel condensation. Both TpTc-POP and TbTc-POP possess hierarchical meso- and micro-pores with a high surface area. Furthermore, the unsubstituted vinylene linkages of D-A moieties in their polymer backbones extend their π-conjugation and render their broad absorption range in the visible-light region. Thus, these DA-POPs exhibited highly effective photocatalytic activities for aerobic oxidative coupling of amines to imines under visible light irradiation. This study shows the great potential of conjugated POPs with a D-A structural feature in designing highly efficient and active heterogeneous photocatalytic systems.
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http://dx.doi.org/10.1039/d1ra06118f | DOI Listing |
Chempluschem
May 2023
State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Center of Smart Materials and Devices, Wuhan University of Technology, Wuhan, 430070, China.
The vinylene-bridged helical perylene diimide (PDI) dimer (PDI2) with a build-in twisted configuration is an alternative building block to the parent PDI for the construction of efficient non-fullerene acceptor (NFAs). Moreover, it has been proved asymmetric strategy plays a vital role in the development of NFAs. Herein, we designed and synthesized a pair of acceptor-donor-acceptor (A-D-A) type PDI2 derivatives, namely IDTIC-PDI and IDT-diPDI2, which contain asymmetric and symmetric end-cap units, respectively.
View Article and Find Full Text PDFChem Asian J
February 2023
State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Center of Smart Materials and Devices, Wuhan University of Technology, Wuhan, 430070, P. R. China.
The vinylene-bridged helical PDI dimer (PDI2) has been an alternative PDI building block for non-fullerene acceptor (NFAs). However, the development of PDI2 derivatives still lag behind, and most of PDI2 derivatives based organic solar cells (OSCs) only achieved a moderate power conversion efficiencies (PCE) of less than 8%. In this contribution, an acceptor-donor-acceptor-donor-acceptor (A-D-A'-D-A) architecture was introduced to facilitate the improvement of photovoltaic properties.
View Article and Find Full Text PDFRSC Adv
October 2021
Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University Xuzhou 221116 P. R. China
Porous organic polymers (POPs), owing to their abundant porosity, high stability and well-tunable properties, are promising candidates as heterogeneous photocatalysts for organic transformations. Here we report two vinylene-bridged donor-acceptor (D-A) structural POPs (TpTc-POP and TbTc-POP) that are facilely constructed by the electron-rich triarylamine and electron-deficient tricyanomesitylene as key building blocks by the organic base catalyzed Knoevenagel condensation. Both TpTc-POP and TbTc-POP possess hierarchical meso- and micro-pores with a high surface area.
View Article and Find Full Text PDFChemistry
June 2022
Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
A family of fully bridged triphenylamines with embedded 5- and 7-membered rings is presented. The compounds are potent electron donors capable to undergo donor/acceptor interactions with strong cyano-based acceptors both in the solid state and solution. These interactions were evaluated by IR and UV/vis spectroscopy as well as X-ray crystallography.
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