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Preparation and Characterization of Small Molecule Acceptor Materials Based on 11,11,12,12-Tetracyano-9,10-anthraquinodimethane with High Electron Affinity

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Abstract

Three small molecules bearing 11,11,12,12-tetracyano-9,10-anthraquinodimethane (TCAQ) units were successfully prepared by a Knoevenagel condensation reaction. Their chemical structures were confirmed by Fourier transform infrared spectrometry and nuclear magnetic resonance (NMR) spectroscopy. They had good solubility, and their optical properties were studied by utilizing ultraviolet–visible absorption spectra in chloroform (CHCl3) solution and thin films. The two conjugated small molecules that connect the donor unit to the acceptor unit with a double bond exhibited a broad and strong absorption band ranging from 200 to 800 nm; their optical band gaps were calculated to be 1.6 eV, suggesting their good coverage of the solar spectrum. Cyclic voltammetry proved that these compounds possess a high electron affinity of ~ 4.0 eV. The results of the photoluminescence quenching experiment reveal efficient electron transfer from poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene vinylene] (MEH-PPV) to the target small molecules. In conclusion, the properties of these molecules make them potential n-type small molecule organic solar cell materials.

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Acknowledgments

This work was supported by the Henan Academy of Sciences (No. 220608001, 210108004 and YZJD202001025). The authors gratefully thank the Analytical & Testing Center of Zhengzhou University and Henan Province Analysis and Test Center for NMR measurements.

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Authors and Affiliations

  1. Henan Chemical Industry Institute Co., Ltd, Zhengzhou, 450052, China

    Erfu Huo, Weiqin Cheng, Ming Feng, Yanhua Wang, Bonan Wang & Hongli Wang

  2. Quality Inspection and Analytical Test Research Center, Henan Academy of Sciences, Zhengzhou, 450008, China

    Erfu Huo & Bonan Wang

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  1. Erfu Huo
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  2. Weiqin Cheng
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  3. Ming Feng
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  4. Yanhua Wang
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Huo, E., Cheng, W., Feng, M. et al. Preparation and Characterization of Small Molecule Acceptor Materials Based on 11,11,12,12-Tetracyano-9,10-anthraquinodimethane with High Electron Affinity. J. Electron. Mater. 51, 5783–5789 (2022). https://doi.org/10.1007/s11664-022-09814-1

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