Modular-Approach Synthesis of Giant Molecule Acceptors via Lewis-Acid-Catalyzed Knoevenagel Condensation for Stable Polymer Solar Cells
Hongyuan Fu
State Key Laboratory of Chemical Resource Engineering, Beijing Advanced Innovation Center for Soft Matter Science and Engineering, Beijing University of Chemical Technology, 100029 Beijing, China
Search for more papers by this authorMing Zhang
State Key Laboratory of Chemical Resource Engineering, Beijing Advanced Innovation Center for Soft Matter Science and Engineering, Beijing University of Chemical Technology, 100029 Beijing, China
Search for more papers by this authorDr. Youdi Zhang
College of Chemistry, Key Laboratory of Advanced Green Functional Materials, Changchun Normal University, 130032 Changchun, China
Search for more papers by this authorQingyuan Wang
State Key Laboratory of Chemical Resource Engineering, Beijing Advanced Innovation Center for Soft Matter Science and Engineering, Beijing University of Chemical Technology, 100029 Beijing, China
Search for more papers by this authorZheng'ao Xu
State Key Laboratory of Chemical Resource Engineering, Beijing Advanced Innovation Center for Soft Matter Science and Engineering, Beijing University of Chemical Technology, 100029 Beijing, China
Search for more papers by this authorDr. Qiuju Zhou
Analysis & Testing Center, Xinyang Normal University, 464000 Xinyang, Henan, China
Search for more papers by this authorZhengkai Li
State Key Laboratory of Chemical Resource Engineering, Beijing Advanced Innovation Center for Soft Matter Science and Engineering, Beijing University of Chemical Technology, 100029 Beijing, China
Search for more papers by this authorYang Bai
State Key Laboratory of Chemical Resource Engineering, Beijing Advanced Innovation Center for Soft Matter Science and Engineering, Beijing University of Chemical Technology, 100029 Beijing, China
Search for more papers by this authorProf. Yongfang Li
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, 100190 Beijing, China
Search for more papers by this authorCorresponding Author
Prof. Zhi-Guo Zhang
State Key Laboratory of Chemical Resource Engineering, Beijing Advanced Innovation Center for Soft Matter Science and Engineering, Beijing University of Chemical Technology, 100029 Beijing, China
Search for more papers by this authorHongyuan Fu
State Key Laboratory of Chemical Resource Engineering, Beijing Advanced Innovation Center for Soft Matter Science and Engineering, Beijing University of Chemical Technology, 100029 Beijing, China
Search for more papers by this authorMing Zhang
State Key Laboratory of Chemical Resource Engineering, Beijing Advanced Innovation Center for Soft Matter Science and Engineering, Beijing University of Chemical Technology, 100029 Beijing, China
Search for more papers by this authorDr. Youdi Zhang
College of Chemistry, Key Laboratory of Advanced Green Functional Materials, Changchun Normal University, 130032 Changchun, China
Search for more papers by this authorQingyuan Wang
State Key Laboratory of Chemical Resource Engineering, Beijing Advanced Innovation Center for Soft Matter Science and Engineering, Beijing University of Chemical Technology, 100029 Beijing, China
Search for more papers by this authorZheng'ao Xu
State Key Laboratory of Chemical Resource Engineering, Beijing Advanced Innovation Center for Soft Matter Science and Engineering, Beijing University of Chemical Technology, 100029 Beijing, China
Search for more papers by this authorDr. Qiuju Zhou
Analysis & Testing Center, Xinyang Normal University, 464000 Xinyang, Henan, China
Search for more papers by this authorZhengkai Li
State Key Laboratory of Chemical Resource Engineering, Beijing Advanced Innovation Center for Soft Matter Science and Engineering, Beijing University of Chemical Technology, 100029 Beijing, China
Search for more papers by this authorYang Bai
State Key Laboratory of Chemical Resource Engineering, Beijing Advanced Innovation Center for Soft Matter Science and Engineering, Beijing University of Chemical Technology, 100029 Beijing, China
Search for more papers by this authorProf. Yongfang Li
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, 100190 Beijing, China
Search for more papers by this authorCorresponding Author
Prof. Zhi-Guo Zhang
State Key Laboratory of Chemical Resource Engineering, Beijing Advanced Innovation Center for Soft Matter Science and Engineering, Beijing University of Chemical Technology, 100029 Beijing, China
Search for more papers by this authorAbstract
The operational stability of polymer solar cells is a critical concern with respect to the thermodynamic relaxation of acceptor-donor-acceptor (A-D-A) or A-DA'D-A structured small-molecule acceptors (SMAs) within their blends with polymer donors. Giant molecule acceptors (GMAs) bearing SMAs as subunits offer a solution to this issue, while their classical synthesis via the Stille coupling suffers from low reaction efficiency and difficulty in obtaining mono-brominated SMA, rendering the approach impractical for their large-scale and low-cost preparation. In this study, we present a simple and cost-effective solution to this challenge through Lewis acid-catalyzed Knoevenagel condensation with boron trifluoride etherate (BF3 ⋅ OEt2) as catalyst. We demonstrated that the coupling of the monoaldehyde-terminated A-D-CHO unit and the methylene-based A-link-A (or its silyl enol ether counterpart) substrates can be quantitatively achieved within 30 minutes in the presence of acetic anhydride, affording a variety of GMAs connected via the flexible and conjugated linkers. The photophysical properties was fully studied, yielding a high device efficiency of over 18 %. Our findings offer a promising alternative for the modular synthesis of GMAs with high yields, easier work up, and the widespread application of such methodology will undoubtedly accelerate the progress of stable polymer solar cells.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
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