Abstract
A couple of novel electrochromic materials poly(2,3,4,5-tetrakis(2,3-hydrothieno[3,4-b]dixin-5-yl)-1-methyl-1H-pyrrole) (P(t-EDOT-mPy)) and poly(5,5′,5′′,5′′′-(thiophene-2,3,4,5-tetrayl)tetrakis(2,3-dihydrothieno[3,4-b][1,4]dioxine)) (P(t-EDOT-Th)) are electrodeposited via multi-position polymerization of their tetra-EDOT substituted monomers t-EDOT-mPy and t-EDOT-Th, respectively. Compared with the linear 2D structured poly(thiophene) (E g=2.2 eV) and poly(2,5-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)thiophene) (E g=1.7 eV), P(t-EDOT-Th) (E g=1.62 eV) has the lowest band gap. Hence, we speculate that the band gaps of the two polymers, having 3D structures, are decreased in contrast to non-substituted polymers or bi-EDOT substituted polymers, thiophene and 1-methyl-1H-pyrrole. The results indicated that P(t-EDOT-Th) thin films are more stable and show higher transmittance amid two polymers, which may find their utilization in organic optoelectronics.
Similar content being viewed by others
References
Mortimer RJ. Annu Rev Mater Res, 2011, 41: 241–268
Remmele J, Shen DE, Mustonen T, Fruehauf N. ACS Appl Mater Interfaces, 2015, 7: 12001–12008
(a)_Yeh MH, Lin L, Yang PK, Wang ZL. ACS Nano, 2015, 9: 4757–4765
Wang Y, Runnerstrom EL, Milliron DJ. Annu Rev Chem Biomol Eng, 2016, 7: 283–304
Mortimer RJ, Dyer AL, Reynolds JR. Displays, 2006, 27: 2–18
Yu H, Shao S, Yan L, Meng H, He Y, Yao C, Xu P, Zhang X, Hu W, Huang W. J Mater Chem C, 2016, 4: 2269–2273
Lehtimäki S, Suominen M, Damlin P, Tuukkanen S, Kvarnström C, Lupo D. ACS Appl Mater Interfaces, 2015, 7: 22137–22147
Sonmez G, Meng H, Wudl F. Chem Mater, 2004, 16: 574–580
Wang C, Gu P, Hu B, Zhang Q. J Mater Chem C, 2015, 3: 10055–10065
Jensen J, Hösel M, Dyer AL, Krebs FC. Adv Funct Mater, 2015, 25: 2073–2090
Beaujuge PM, Reynolds JR. Chem Rev, 2010, 110: 268–320
Tagmouti S, Outzourhit A, Oueriagli A, Khaidar M, Elyacoubi M, Evrard R, Ameziane EL. Sol Energ Mat Sol C, 2002, 71: 9–18
Lin R, Stokbro K, Madsen DN, Boubour E, Bøggild P. Thin Solid Films, 2005, 484: 334–340
Roncali J, Blanchard P, Frère P. J Mater Chem, 2005, 15: 1589–1610
Huang JH, Hsu CY, Hu CW, Chu CW, Ho KC. ACS Appl Mater Interfaces, 2010, 2: 351–359
Agrawal V, Shahjad V, Bhardwaj D, Bhargav R, Sharma GD, Bhardwaj RK, Patra A, Chand S. Electrochim Acta, 2016, 192: 52–60
Shi J, Zhu X, Xu P, Zhu M, Guo Y, He Y, Hu Z, Murtaza I, Yu H, Yan L, Goto O, Meng H. Macromol Rapid Commun, 2016, 37: 1344–1351
Taerum T, Lukoyanova O, Wylie RG, Perepichka DF. Org Lett, 2009, 11: 3230–3233
Xu C, Zhao J, Cui C, Wang M, Kong Y, Zhang X. J Electroanal Chem, 2012, 682: 29–36
Piron F, Leriche P, Mabon G, Grosu I, Roncali J. Electrochem Commun, 2008, 10: 1427–1430
Zhong YP, Gao JM, Liu P, Deng WJ. Mater Res Innov, 2015, 19: 51–54
Zhang K, Tieke B, Forgie JC, Vilela F, Parkinson JA, Skabara PJ. Polymer, 2010, 51: 6107–6114
Vilela F, Zhang K, Antonietti M. Energ Environ Sci, 2012, 5: 7819–7832
Liu Y, Kanhere PD, Ling Wong C, Tian Y, Feng Y, Boey F, Wu T, Chen H, White TJ, Chen Z, Zhang Q. J Solid State Chem, 2010, 183: 2644–2649
Gilow HM, Burton DE. J Org Chem, 1981, 46: 2221–2225
Sadekar AG, Mohite D, Mulik S, Chandrasekaran N, Sotiriou-Leventis C, Leventis N. J Mater Chem, 2012, 22: 100–108
Meng H, Perepichka DF, Wudl F. Angew Chem Int Ed, 2003, 42: 658–661
Sotzing GA, Reddinger JL, Katritzky AR, Soloducho J, Musgrave R, Reynolds JR, Steel PJ. Chem Mater, 1997, 9: 1578–1587
Li Y. J Electroanal Chem, 1997, 433: 181–186
Poverenov E, Li M, Bitler A, Bendikov M. Chem Mater, 2010, 22: 4019–4025
Evans DH. Chem Rev, 1990, 90: 739–751
Roncali J. Chem Rev, 1992, 92: 711–738
Andrieux CP, Audebert P, Hapiot P, Saveant JM. J Am Chem Soc, 1990, 112: 2439–2440
Kumar A, Welsh DM, Morvant MC, Piroux F, Abboud KA, Reynolds JR. Chem Mater, 1998, 10: 896–902
San Miguel L, Porter WW, Matzger AJ. Org Lett, 2007, 9: 1005–1008
Durmus A, Gunbas GE, Toppare L. Chem Mater, 2007, 19: 6247–6251
Sotzing GA, Reddinger JL, Reynolds JR, Steel PJ. Synth Met, 1997, 84: 199–201
Ak M, Ak MS, Kurtay G, Güllü M, Toppare L. Solid State Sci, 2010, 12: 1199–1204
Li M, Wei Y, Zheng J, Zhu D, Xu C. Org Electron, 2014, 15: 428–434
Kim HN, Cho SM, Ah CS, Song J, Ryu H, Kim YH, Kim TY. Mater Res Bull, 2016, 82: 16–21
Kim H, Park Y, Choi D, Ahn SH, Lee CS. Appl Surface Sci, 2016, 377: 370–375
Knott EP, Craig MR, Liu DY, Babiarz JE, Dyer AL, Reynolds JR. J Mater Chem, 2012, 22: 4953–4962
Guan S, Elmezayyen AS, Zhang F, Zheng J, Xu C. J Mater Chem C, 2016, 4: 4584–4591
Acknowledgments
This work was supported by the Shenzhen Key Laboratory of Organic Optoelectromagnetic Functional Materials of Shenzhen Science and Technology Plan (ZDSYS20140509094114164), the Shenzhen Peacock Program (KQTD2014062714543296), Shenzhen Science and Technology Research Grant (JCYJ20140509093817690), the Nanshan Innovation Agency Grant (KC2015ZDYF0016A), the Guangdong Key Research Project (2014B090914003, 2015B090914002), the Guangdong Talents Project, the National Basic Research Program of China (2015CB856505), the National Natural Science Foundation of China (51373075), the Guangdong Academician Workstation (2013B090400016), and the Natural Science Foundation of Guangdong Province (2014A030313800).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Shi, J., Murtaza, I., Shao, S. et al. Tetra-EDOT substituted 3D electrochromic polymers with lower band gaps. Sci. China Chem. 60, 90–98 (2017). https://doi.org/10.1007/s11426-016-0303-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-016-0303-0