Synthesis and electrochromic properties of a carbazole and diketopyrrolopyrrole-based small molecule semiconductor

Bogyu Lim; Song-Yi Han; Seo-Hyun Jung; Yu Jin Jung; Jong Mok Park; Wonjoo Lee; Hee-Sang Shim; Yoon-Chae Nah

Journal of Industrial and Engineering Chemistry, Vol.80, 93-97, December, 2019

DOI10.1016/j.jiec.2019.07.035 Export Citation

Synthesis and electrochromic properties of a carbazole and diketopyrrolopyrrole-based small molecule semiconductor

Bogyu Lim^{1, 2}, Song-Yi Han³, Seo-Hyun Jung¹, Yu Jin Jung¹, Jong Mok Park¹, Wonjoo Lee⁴, Hee-Sang Shim⁵, and Yoon-Chae Nah^{3, †}

¹Green Fine Chemical Research Center, Advanced Convergent Chemistry Division, Korea Research Institute of Chemical Technology (KRICT), 45 Jongga-ro, Jung-gu, Ulsan, 44412, Republic of Korea
²Future Technology Research Center, Corporate R&D, LG Chem R&D Campus Seoul, LG Science Park, 30 Magokjungang 10-ro, Gangseo-gu, Seoul 07796, Republic of Korea
³IPCE, School of Energy, Materials, and Chemical Engineering, Korea University of Technology and Education, 1600 Chungjeol-ro, Cheonan, Chungnam 31253, Republic of Korea
⁴Department of Military Science, Daeduk University, 68 Gajeongbuk-ro, Yuseong-gu, Daejeon 34111, Republic of Korea
⁵Nuclear Materials Research Division, Korea Atomic Energy Research Institute, 989-111 Daedeok-daero, Yuseong-gu, Daejeon 34057, Republic of Korea

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Carbazoles are excellent chromophores for electrochromic (EC) applications owing to their exceptional oxidation properties. Herein, we synthesized a donor-acceptor-type small molecule semiconductor, named LGC-D023, containing carbazole as a core donor, diketopyrrolopyrrole as a weak-acceptor π-linker, and 3-octylrhodanine as an electron-acceptor end-unit; and characterized its optical, thermal, and EC properties. LGC-D023 exhibited good organic solvent solubility, as well as distinct melting and crystallization transitions above 200 °C. Spectroelectrochemical spectra showed blue (L*: 88.28, a*: -6.56, b*: -1.29)-to-red (L*: 93.61, a*: 2.94, b*: -0.75) color switching with a high optical contrast (35.3%), fast response time (>0.3 s), and desirable coloration efficiency (91.9 cm2/C). These results confirmed that this donor-acceptor small molecule could be a new promising candidate for an EC material.

Keywords:Small molecule;Donor-Acceptor;Carbazole;Diketopyrrolopyrrole;Electrochromism

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[1] Monk PMS, Mortimer RJ, Rosseinsky DR, Electrochromism, Wiley-VCH Verlag GmbH, pp.22 2007.

[2] Granqvist CG, Thin Solid Films, 564, 1 (2014)

[3] Mortimer RJ, Dyer AL, Reynolds JR, Displays, 27, 2 (2006)

[4] Richardson TJ, Slack JL, Armitage RD, Kostecki R, Farangis B, Rubin MD, Appl. Phys. Lett., 78, 3047 (2001)

[5] Invernale MA, Ding Y, Sotzing GA, ACS Appl. Mater. Interfaces, 2, 296 (2010)

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[7] Beaujuge PM, Reynolds JR, Chem. Rev., 110(1), 268 (2010)

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[9] Iqbal S, Ahmad S, J. Ind. Eng. Chem., 60, 53 (2018)

[10] Rajamalli P, Senthilkumar N, Gandeepan P, Huang PY, Huang MJ, Ren-Wu CZ, Yang CY, Chiu MJ, Chu LK, Lin HW, Cheng CH, J. Am. Chem. Soc., 138(2), 628 (2016)

[11] Li J, Liu D, Li Y, Lee CS, Kwong HL, Lee S, Chem. Mater., 17, 1208 (2005)

[12] Im Y, Han SH, Lee JY, J. Ind. Eng. Chem., 66, 381 (2018)

[13] Li J, Grimsdale AC, Chem. Soc. Rev., 39, 2399 (2010)

[14] Sathiyan G, Sivakumar EKT, Ganesamoorthy R, Thangamuthu R, Sakthivel R, Tetrahedron Lett., 57, 243 (2016)

[15] Song KW, Choi MH, Lee JY, Moon DK, J. Ind. Eng. Chem., 20(1), 290 (2014)

[16] Wu YL, Li YN, Gardner S, Ong BS, J. Am. Chem. Soc., 127(2), 614 (2005)

[17] Reig M, Puigdollers J, Velasco D, J. Mater. Chem. C, 3, 506 (2015)

[18] Xu JW, Chua MH, Shah KW, Electrochromic Smart Materials: Royal Society of Chemistry, London, 2019.

[19] Pang YH, Li XY, Ding HL, Shi GY, Jin LT, Electrochim. Acta, 52(20), 6172 (2007)

[20] Poverenov E, Li M, Bitler A, Bendikov M, Chem. Mater., 22, 4019 (2010)

[21] Wei HG, Zhu JH, Wu SJ, Wei SY, Guo ZH, Polymer, 54(7), 1820 (2013)

[22] Camurlu P, RSC Adv., 4, 55832 (2014)

[23] Xu Z, Zhang YL, Wang BZ, Liu Z, Zhao JS, Xie Y, Electrochim. Acta, 302, 373 (2019)

[24] Guzel M, Jaratas E, Ak M, Smart Mater. Struc., 28, 025015 (2019)

[25] Kocaeren AA, Org. Electron., 24, 219 (2015)

[26] Usluer O, Koyuncu S, Demic S, Janssen RAJ, J. Polym. Sci. B: Polym. Phys., 49(5), 333 (2011)

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[28] Witker D, Reynolds JR, Macromolecules, 38(18), 7636 (2005)

[29] Lim B, Han SY, Nah YC, Org. Electron, 63, 23 (2018)

[30] Nho S, Kim DH, Park S, Tran HN, Lim B, Cho S, Dyes Pigment., 151, 272 (2018)

[31] Sun JP, Hendsbee AD, Eftaiha AF, Macaulay C, Rutledge LR, Welch GC, Hill IG, J. Mater. Chem. C, 2, 2612 (2014)

[32] Zhang Y, Kong L, Ju X, Du H, Zhao J, Xie Y, RSC Adv., 8, 21252 (2018)