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Synthesis and Opto-Electrical Properties of Novel Conjugated Small Molecule Bearing a B←N Moiety

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Abstract

Effects of the B←N unit on the energy level of conjugated small molecule were investigated by synthesizing a new small molecule BPDPP (3,8-bis(5-(2,5-dioctyl-3,6-dioxo-4-(thiophen-2-yl)-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrol-1-yl)-thiophen-2-yl)-6,6-dioctyl-6H-benzo[3,4] [1,2]azaborolo[1,5-a]pyridin-5-ium-6-uide) via Suzuki coupling. For comparison, CPDPP (6,6′-(5,5′-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(thiophene-5,2-diyl))bis(2,5-dioctyl-3-(thiophen-2-yl)pyrrolo[3,4-c] pyrrole-1,4(2H,5H)-dione)) having the same chemical structure with BPDPP except the B←N unit is synthesized through the same coupling reaction. Absorption spectra and cyclovoltammetry analysis for these small molecules revealed that the B←N unit reduces the band gap of BPDPP by maintaining large oxidation potential. As a result, the blend film of BPDPP and PC71BM maintained 87.4% of the initial absorption intensity after 1sun light soaking test for 315 h. The photo stability of the BPDPP is significantly higher than the blend film of P3HT: PC71BM, which maintained only 19.8% of the initial absorption intensity only after light soaking for 23 h.

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Acknowledgment

This work was supported by the Ewha Womans University Research Grant of 2018.

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Authors and Affiliations

  1. Department of Chemistry and Nanoscience, Ewha Womans University, Seoul, 03760, Korea

    Ka Yeon Ryu, Dan-Bi Sung, Yong-Ju Kwon, Hyun Yeong Kim, Chongmok Lee, Won-Suk Kim & Kyungkon Kim

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  1. Ka Yeon Ryu
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Correspondence to Won-Suk Kim or Kyungkon Kim.

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Information is available regarding the experimental details for the NMR spectra and MALDI-TOF mass spectra. The materials are available via the Internet at http://www.springer.com/13233.

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Ryu, K.Y., Sung, DB., Kwon, YJ. et al. Synthesis and Opto-Electrical Properties of Novel Conjugated Small Molecule Bearing a B←N Moiety. Macromol. Res. 28, 919–924 (2020). https://doi.org/10.1007/s13233-020-8113-1

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