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Red-to-black electrochromism of 4,9-dihydro-s-indaceno[1,2-b:5,6-b’]dithiophene-embedded conjugated polymers

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Abstract

A series of 4,9-dihydro-s-indaceno[1,2-b:5,6-b′]dithiophene-based conjugated polymers with 3,4-bis(dodecyloxy)thiophene, 3,3-bis((dodecyloxy)methyl)-3,4-dihydro-2H-thieno[3,4-b] [1, 4] dioxepine and 3,4-ethylenedioxythiophene as co-monomers were synthesized via Stille coupling reaction in more than 50 % yields. These polymers possess relatively high number-average molecular weights of 14,900–21,000 g mol−1 and exhibit good solubility in common organic solvents. The physical and electrochemical properties of these polymers were studied, and the polymers showed optical bandgap between 2.04 and 2.08 eV. Electrochromic devices showed a rare and reversible colour change between dark red at neutral state and black at oxidized state with optical switching contrast ratios of up to 50 % at λ max and 90 % at 1500 nm in the visible and NIR regions, respectively.

Graphical abstract

4,9-dihydro-s-indaceno[1,2-b:5,6-b’]dithiophene-based conjugated polymers showing rare and reversible colour change between dark red at neutral state and black at oxidized state were synthesized via Stille coupling. These polymers possess high optical contrast in both the visible and NIR regions.

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Acknowledgements

The authors would like to thank the Agency for Science, Technology and Research (A*STAR) and Minister of National Development (MND) for financial support (Grant No.: 1321760011). The TD-DFT calculations were supported by the A*STAR computational resource centre through the use of its high-performance computing facilities.

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Authors and Affiliations

  1. Institute of Materials Research and Engineering, A*STAR, 3 Research Link, Singapore, 117602, Singapore

    Ching Mui Cho, Qun Ye, Wei Teng Neo, Tingting Lin, Jing Song & Jianwei Xu

  2. NUS Graduate School for Integrative Sciences and Engineering, National University of Singapore, 28 Medical Drive, Singapore, 117456, Singapore

    Wei Teng Neo

  3. Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543, Singapore

    Jianwei Xu

  4. School of Materials Science and Engineering, Nanyang Technological University, 50 Nanyang Avenue, Singapore, 639798, Singapore

    Ching Mui Cho & Xuehong Lu

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  1. Ching Mui Cho
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Correspondence to Jianwei Xu.

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Cho, C.M., Ye, Q., Neo, W.T. et al. Red-to-black electrochromism of 4,9-dihydro-s-indaceno[1,2-b:5,6-b’]dithiophene-embedded conjugated polymers. J Mater Sci 50, 5856–5864 (2015). https://doi.org/10.1007/s10853-015-9135-5

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