CC BY-NC-ND 4.0 · Organic Materials 2021; 03(02): 204-213
DOI: 10.1055/a-1472-7109
Focus Issue: Peter Bäuerle 65th Birthday
Original Article

Influence of the Location of Electron-Donating 3,4-Ethylenedioxythiophene (EDOT) Moiety in the A–π–D–π–A Type Conjugated Molecules on the Optoelectronic Properties and Photovoltaic Performances

Lilei Wang
a   Printable Electronics Research Center, Suzhou Institute of Nano-Tech and Nano-Bionics (SINANO), Chinese Academy of Sciences, 398 Ruo Shui Road, SEID SIP, Suzhou, Jiangsu, 215123, P. R. China
b   Department of Chemistry, Shanghai Key Laboratory of Green Chemistry and Chemical, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. China
,
Ying Zhang
c   College of Chemistry, Beijing Normal University, 19 XinJieKouWai Street, HaiDian District Beijing 100875, P. R. China
,
Xiang Guan
a   Printable Electronics Research Center, Suzhou Institute of Nano-Tech and Nano-Bionics (SINANO), Chinese Academy of Sciences, 398 Ruo Shui Road, SEID SIP, Suzhou, Jiangsu, 215123, P. R. China
,
Wei Gao
a   Printable Electronics Research Center, Suzhou Institute of Nano-Tech and Nano-Bionics (SINANO), Chinese Academy of Sciences, 398 Ruo Shui Road, SEID SIP, Suzhou, Jiangsu, 215123, P. R. China
,
Yi Lin 
d   Department of Chemistry, Xi'an Jiaotong Liverpool University, 111 Ren Ai Road, SEID SIP, Suzhou, Jiangsu, 215123, P. R. China
,
Qun Luo 
a   Printable Electronics Research Center, Suzhou Institute of Nano-Tech and Nano-Bionics (SINANO), Chinese Academy of Sciences, 398 Ruo Shui Road, SEID SIP, Suzhou, Jiangsu, 215123, P. R. China
,
Hongwei Tan
c   College of Chemistry, Beijing Normal University, 19 XinJieKouWai Street, HaiDian District Beijing 100875, P. R. China
,
Hai-Bo Yang 
b   Department of Chemistry, Shanghai Key Laboratory of Green Chemistry and Chemical, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. China
,
Chang-Qi Ma 
a   Printable Electronics Research Center, Suzhou Institute of Nano-Tech and Nano-Bionics (SINANO), Chinese Academy of Sciences, 398 Ruo Shui Road, SEID SIP, Suzhou, Jiangsu, 215123, P. R. China
› Author Affiliations Funding Information Financial support for this project was provided by the National Natural Science Foundation of China (22075315) and by Xi'an Jiaotong-Liverpool University Research Development Fund (RDF-14-02-46).
› Further Information
   Permissions and Reprints All articles of this category


Abstract

A–π–D–π–A type conjugated small molecules play an indispensable role in organic photovoltaics. Understanding the relationship between the molecular structure and performance is a fundamental question for the further rational design of high-performance organic materials. To red-shift the absorption spectrum of benzo[1,2-b:4,5-b']dithiophene (BDT) based A–π–D–π–A type compounds, an electron-donating 3,4-ethylenedioxythiophene (EDOT) moiety was introduced into the π-conjugation bridge unit. Two new compounds with EDOT next to the central BDT core (COOP-2HT-EDOT-BDT) or next to the terminal electron acceptor unit (COOP-EDOT-2HT-BDT) were synthesized and characterized. The compound COOP-2HT-EDOT-BDT showed higher molar extinction coefficient (εabs max = 1.06 × 105 L mol−1 cm−1), lower optical band gap (E g = 1.56 eV) and high HOMO energy level (E HOMO = −5.08 eV) than COOP-EDOT-2HT-BDT (εabs max = 0.96 × 105 L mol−1 cm−1, E g = 1.71 eV, E HOMO = −5.26 eV), which is attributed to the intensive interaction between the EDOT unit and the HOMO orbital, as confirmed by the theoretical calculation results. However, the higher power conversion efficiency of 3.58% was achieved for the COOP-EDOT-2HT-BDT:PC61BM-based solar cells, demonstrating that the electron-donating EDOT unit adjacent to the electron-withdrawing end-capped group (COOP) is a better way to achieve high-performance photovoltaic materials.

Key words

organic solar cells - organic semiconductors - A–π–D–π–A small molecules - benzo[1,2-b:4,5-b′]dithiophene derivatives - 3,4-ethylenedioxythiophene

Supporting Information

Supporting information for this article is available online at https://doi.org/10.1055/a-1472-7109.


Dedication to Prof. Peter Bäuerle on the occasion of his 65th birthday.


Supporting Information



Publication History

Received: 11 February 2021

Accepted: 16 March 2021

Accepted Manuscript online:
01 April 2021

Article published online:
26 May 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

    • 1a Lin Y, Zhan X. Acc. Chem. Res. 2016; 49: 175
      CrossrefPubMed
    • 1b Hou J, Inganäs O, Friend RH, Gao F. Nat. Mater. 2018; 17: 119
      CrossrefPubMed
    • 1c Ye W, Yang Y, Zhang Z, Zhu Y, Ye L, Miao C, Lin Y, Zhang S. Sol. RRL 2020; 4: 2000258
      CrossrefPubMed
    • 1d Kan B, Kan Y, Zuo L, Shi X, Gao K. InfoMat 2021; 3: 175
      CrossrefPubMed
    • 2a Tang H, Yan C, Huang J, Kan Z, Xiao Z, Sun K, Li G, Lu S. Matter 2020; 3: 1403
      CrossrefPubMed
    • 2b Zheng B, Huo L. Sci. China Chem. 2021; 64: 358
      CrossrefPubMed
    • 3a Min J, Cui C, Heumueller T, Fladischer S, Cheng X, Spiecker E, Li Y, Brabec CJ. Adv. Energy Mater. 2016; 6: 1600515
      CrossrefPubMed
    • 3b Lee CJ, Mitchell VD, White J, Jiao X, McNeill CR, Subbiah J, Jones DJ. J. Mater. Chem. A 2019; 7: 6312
      CrossrefPubMed
    • 3c Subbiah J, Lee CJ, Mitchell VD, Jones DJ. ACS Appl. Mater. Interfaces 2021; 13: 1086
      CrossrefPubMed
    • 4a Qiu B, Xue L, Yang Y, Bin H, Zhang Y, Zhang C, Xiao M, Park K, Morrison W, Zhang Z.-G, Li Y. Chem. Mater. 2017; 29: 7543
      CrossrefPubMed
    • 4b Bin H, Yang Y, Zhang Z.-G, Ye L, Ghasemi M, Chen S, Zhang Y, Zhang C, Sun C, Xue L, Yang C, Ade H, Li Y. J. Am. Chem. Soc. 2017; 139: 5085
      CrossrefPubMed
    • 4c Duan T, Tang H, Liang R.-Z, Lv J, Kan Z, Singh R, Kumar M, Xiao Z, Lu S, Laquai F. J. Mater. Chem. A 2019; 7: 2541
      CrossrefPubMed
    • 5a Wang L, Zhang Y, Yin N, Lin Y, Gao W, Luo Q, Tan H, Yang H.-B, Ma C.-Q. Sol. Energy Mater. Sol. Cells 2016; 157: 831
      CrossrefPubMed
    • 5b Wang K, Liang R.-Z, Wolf J, Saleem Q, Babics M, Wucher P, Abdelsamie M, Amassian A, Hansen MR, Beaujuge PM. Adv. Funct. Mater. 2016; 26: 7103
      CrossrefPubMed
    • 5c Wan J, Xu X, Zhang G, Li Y, Feng K, Peng Q. Energy Environ. Sci. 2017; 10: 1739
      CrossrefPubMed
    • 5d Huo Y, Gong X.-T, Lau T.-K, Xiao T, Yan C, Lu X, Lu G, Zhan X, Zhang H.-L. Chem. Mater. 2018; 30: 8661
      CrossrefPubMed
    • 5e Wu Q, Deng D, Zhang J, Zou W, Yang Y, Wang Z, Li H, Zhou R, Lu K, Wei Z. Sci. China Chem. 2019; 62: 837
      CrossrefPubMed
  • 6 Qin J, An C, Zhang J, Ma K, Yang Y, Zhang T, Li S, Xian K, Cui Y, Tang Y, Ma W, Yao H, Zhang S, Xu B, He C, Hou J. Sci. China Mater. 2020; 63: 1142
    CrossrefPubMed
    • 7a Roncali J, Blanchard P, Frère P. J. Mater. Chem. 2005; 15: 1589
      CrossrefPubMed
    • 7b Wang Q, Zeng Z, Li Y, Chen X. Sol. Energy 2020; 208: 10
      CrossrefPubMed
    • 7c Ming S, Li Z, Zhen S, Liu P, Jiang F, Nie G, Xu J. Chem. Eng. J. 2020; 390: 124572
      CrossrefPubMed
  • 8 Beaujuge PM, Amb CM, Reynolds JR. Acc. Chem. Res. 2010; 43: 1396
    CrossrefPubMed
  • 9 Montcada NF, Domínguez R, Pelado B, Cruz Pl, Palomares E, Langa F. J. Mater. Chem. A 2015; 3: 11340
    CrossrefPubMed
  • 10 Hwang Y.-J, Li H, Courtright BA. E, Subramaniyan S, Jenekhe SA. Adv. Mater. 2016; 28: 124
    CrossrefPubMed
  • 11 Wu Y, Wang Z, Liang M, Cheng H, Li M, Liu L, Wang B, Wu J, Prasad Ghimire R, Wang X, Sun Z, Xue S, Qiao Q. ACS Appl. Mater. Interfaces 2018; 10: 17883
    CrossrefPubMed
  • 12 Trippé-Allard G, Lacroix J.-C. Tetrahedron 2013; 69: 861
    CrossrefPubMed
    • 13a Cremer J, Mena-Osteritz E, Pschierer NG, Müllen K, Bäuerle P. Org. Biomol. Chem. 2005; 3: 985
      CrossrefPubMed
    • 13b Weidelener M, Wessendorf CD, Hanisch J, Ahlswede E, Götz G, Lindén M, Schulz G, Mena-Osteritz E, Mishra A, Bäuerle P. Chem. Commun. 2013; 49: 10865
      CrossrefPubMed
  • 14 Jessing M, Brandt M, Jensen KJ, Christensen JB, Boas U. J. Org. Chem. 2006; 71: 6734
    CrossrefPubMed
  • 15 Medlej H, Awada H, Abbas M, Wantz G, Bousquet A, Grelet E, Hariri K, Hamieh T, Hiorns RC, Dagron-Lartigau C. Eur. Polym. J. 2013; 49: 4176
    CrossrefPubMed
  • 16 Marques dos Santos J, Neophytou M, Wiles A, Howells CT, Ashraf RS, McCulloch I, Cooke G. Dyes Pigm. 2021; 188: 109152
    CrossrefPubMed
    • 17a Li Z, He G, Wan X, Liu Y, Zhou J, Long G, Zuo Y, Zhang M, Chen Y. Adv. Energy Mater. 2012; 2: 74
      CrossrefPubMed
    • 17b Long G, Wan X, Kan B, Liu Y, He G, Li Z, Zhang Y, Zhang Y, Zhang Q, Zhang M, Chen Y. Adv. Energy Mater. 2013; 3: 639
      CrossrefPubMed
    • 18a Yao Z.-F, Wang J.-Y, Pei J. Cryst. Growth Des. 2018; 18: 7
      CrossrefPubMed
    • 18b Li Y, Lee DH, Lee J, Nguyen TL, Hwang S, Park MJ, Choi DH, Woo HY. Adv. Funct. Mater. 2017; 27: 1701942
      CrossrefPubMed
    • 19a Ma C.-Q, Mena-Osteritz E, Wunderlin M, Schulz G, Bäuerle P. Chem. Eur. J. 2012; 18: 12880
      CrossrefPubMed
    • 19b Adams RN. Electrochemistry at Solid electrode. Marcel Dekker, Inc.; New York: 1969
      Google Scholar
  • 20 Cardona CM, Li W, Kaifer AE, Stockdale D, Bazan GC. Adv. Mater. 2011; 23: 2367
    CrossrefPubMed
  • 21 Yin N, Wang L, Lin Y, Yi J, Yan L, Dou J, Yang H.-B, Zhao X, Ma C.-Q. Beilstein J. Org. Chem. 2016; 12: 1788
    CrossrefPubMed
    • 22a Yan C, Barlow S, Wang Z, Yan H, Jen AK. Y, Marder SR, Zhan X. Nat. Rev. Mater. 2018; 3: 18003
      CrossrefPubMed
    • 22b Wadsworth A, Moser M, Marks A, Little MS, Gasparini N, Brabec CJ, Baran D, McCulloch I. Chem. Soc. Rev. 2019; 48: 1596
      CrossrefPubMed
    • 22c Meredith P, Li W, Armin A. Adv. Energy Mater. 2020; 10: 2001788
      CrossrefPubMed
    • 23a Liu Q, Jiang Y, Jin K, Qin J, Xu J, Li W, Xiong J, Liu J, Xiao Z, Sun K, Yang S, Zhang X, Ding L. Sci. Bull. 2020; 65: 272
      CrossrefPubMed
    • 23b Zhang M, Zhu L, Zhou G, Hao T, Qiu C, Zhao Z, Hu Q, Larson BW, Zhu H, Ma Z, Tang Z, Feng W, Zhang Y, Russell TP, Liu F. Nat. Commun. 2021; 12: 309
      CrossrefPubMed
  • 24 Bi P, Hao X. Sol. RRL 2019; 3: 1800263
    CrossrefPubMed