End-cap Group Engineering of a Small Molecule Non-Fullerene Acceptor: The Influence of Benzothiophene DioxideClick to copy article linkArticle link copied!
- Hongda CaoHongda CaoDepartment of Chemistry and Biochemistry, The University of Alabama, Tuscaloosa, Alabama 35487, United StatesMore by Hongda Cao
- Nicole BauerNicole BauerDepartment of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United StatesMore by Nicole Bauer
- Chao PangChao PangState Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Nanjing Tech University, Nanjing, Jiangsu 210009, P. R. ChinaCenter for Materials for Information Technology (MINT), The University of Alabama, Tuscaloosa, Alabama 35487, United StatesMore by Chao Pang
- Jeromy RechJeromy RechDepartment of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United StatesMore by Jeromy Rech
- Wei YouWei YouDepartment of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United StatesMore by Wei You
- Paul A. Rupar*Paul A. Rupar*E-mail: [email protected]Department of Chemistry and Biochemistry, The University of Alabama, Tuscaloosa, Alabama 35487, United StatesMore by Paul A. Rupar
Abstract
![Abstract Image](/cms/10.1021/acsaem.8b01576/asset/images/medium/ae-2018-01576v_0008.gif)
In this study, a sulfonyl-containing end-capping moiety, benzothiophene dioxide, was selected to prepare the nonfullerene acceptor ITBC. ITBC has an acceptor–donor–acceptor (A-D-A) structure, with indacenodithieno[3,2-b]thiophene (IDTT) as the electron-rich core moiety. The strong electron-withdrawing sulfonyl acceptor units leads to extended UV–vis absorption into the near-IR region and relatively low frontier molecular orbital energy levels (LUMO/HOMO: −4.13 eV/–5.61 eV) with a narrow bandgap of 1.48 eV. These values compare favorably to the well-studied small molecule acceptor 2-(3-oxo-2,3-dihydroinden-1-ylidene)malononitrile end-capped indacenodithieno[3,2-b]thiophene (ITIC). A power conversion efficiency of 4.17% was achieved by fabricating organic solar cells with the fluorinated conjugated polymer FTAZ as the donor and ITBC as the acceptor. These results indicate that benzothiophene dioxide is a novel electron-withdrawing end-capping unit for ITBC, and can be used as an electron acceptor for organic solar cells.
Cited By
This article is cited by 13 publications.
- Azzaya Khasbaatar, Zhuang Xu, Jong-Hoon Lee, Gonzalo Campillo-Alvarado, Changhyun Hwang, Brandon N. Onusaitis, Ying Diao. From Solution to Thin Film: Molecular Assembly of π-Conjugated Systems and Impact on (Opto)electronic Properties. Chemical Reviews 2023, 123
(13)
, 8395-8487. https://doi.org/10.1021/acs.chemrev.2c00905
- Bettina Schweda, Matiss Reinfelds, Petra Hofstadler, Gregor Trimmel, Thomas Rath. Recent Progress in the Design of Fused-Ring Non-Fullerene Acceptors─Relations between Molecular Structure and Optical, Electronic, and Photovoltaic Properties. ACS Applied Energy Materials 2021, 4
(11)
, 11899-11981. https://doi.org/10.1021/acsaem.1c01737
- Lupiao Tao, Xiaohui Liu, Changbo Deng, Wenjun Zhang, Weijie Song. Highly Efficient Nonfullerene Acceptor with Sulfonyl-Based Ending Groups. ACS Applied Materials & Interfaces 2020, 12
(44)
, 49659-49665. https://doi.org/10.1021/acsami.0c14774
- Taylor G. Allen, Sepehr Benis, Natalia Munera, Junxiang Zhang, Shuixing Dai, Tengfei Li, Boyu Jia, Wei Wang, Stephen Barlow, David J. Hagan, Eric W. Van Stryland, Xiaowei Zhan, Joseph W. Perry, Seth R. Marder. Highly Conjugated, Fused-Ring, Quadrupolar Organic Chromophores with Large Two-Photon Absorption Cross-Sections in the Near-Infrared. The Journal of Physical Chemistry A 2020, 124
(22)
, 4367-4378. https://doi.org/10.1021/acs.jpca.0c02572
- Francis Lin, Lijian Zuo, Ke Gao, Ming Zhang, Sae Byeok Jo, Feng Liu, Alex K.-Y. Jen. Regio-Specific Selenium Substitution in Non-Fullerene Acceptors for Efficient Organic Solar Cells. Chemistry of Materials 2019, 31
(17)
, 6770-6778. https://doi.org/10.1021/acs.chemmater.9b01242
- Muhammad Khalid, Gang Wu, Areeha Umber, Mashal Khan, Ataualpa A.C. Braga, Norah Alhokbany, Suvash Chandra Ojha. Impact of extended π-conjugated acceptor moieties on non-linear optical behavior in polar medium for designed 4,4-dimethyl-4H-indeno[1,2-b] thiophene based materials. Journal of Molecular Liquids 2024, 401 , 124608. https://doi.org/10.1016/j.molliq.2024.124608
- Sheik Haseena, Mahesh Kumar Ravva. Application of Newly Designed Y‐Series Nonfullerene Acceptors for High‐Efficient Organic Solar Cells. Advanced Theory and Simulations 2023, 6
(6)
https://doi.org/10.1002/adts.202200898
- Rudranarayan Khatua, Bibhas Das, Anirban Mondal. Rational design of non-fullerene acceptors
via
side-chain and terminal group engineering: a computational study. Physical Chemistry Chemical Physics 2023, 25
(11)
, 7994-8004. https://doi.org/10.1039/D2CP05958D
- Seungyun Baik, Dong Won Kim, Hyun-Sik Kang, Seung Hwa Hong, Sungjin Park, Byeong-Kwan An, Soo Young Park. ITIC derivative acceptors for ternary organic solar cells: fine-tuning of absorption bands, LUMO energy levels, and cascade charge transfer. Sustainable Energy & Fuels 2021, 6
(1)
, 110-120. https://doi.org/10.1039/D1SE01429C
- Martina Marinelli, Andrea Candini, Filippo Monti, Alex Boschi, Mattia Zangoli, Elisabetta Salatelli, Filippo Pierini, Massimiliano Lanzi, Alberto Zanelli, Massimo Gazzano, Francesca Di Maria. Push–pull thiophene-based small molecules with donor and acceptor units of varying strength for photovoltaic application: beyond P3HT and PCBM. Journal of Materials Chemistry C 2021, 9
(34)
, 11216-11228. https://doi.org/10.1039/D1TC02641K
- Thu Trang Do, Meera Stephen, Khai Leok Chan, Sergei Manzhos, Paul L. Burn, Prashant Sonar. Pyrrolo[3,2-b]pyrrole-1,4-dione (IsoDPP) End Capped with Napthalimide or Phthalimide: Novel Small Molecular Acceptors for Organic Solar Cells. Molecules 2020, 25
(20)
, 4700. https://doi.org/10.3390/molecules25204700
- Jian Cao, Shiqi Li, Hua-Chun Wang, Si-Jie Bai, Zhangyan Wang, Xiancheng Ren, Yun-Xiang Xu. Distinct luminescent properties between thiophene-S-oxide and Thiophene-S, S-dioxides incorporated ladder-type molecules. Dyes and Pigments 2020, 175 , 108147. https://doi.org/10.1016/j.dyepig.2019.108147
- Ratna Dewi Maduwu, Ho Cheol Jin, Joo Hyun Kim. Synthesis and Characterization of Benzothiadiazole and Dicyanovinylindandione Based Small-Molecular Conjugated Materials and Their Photovoltaic Properties. Macromolecular Research 2019, 27
(12)
, 1261-1267. https://doi.org/10.1007/s13233-019-7174-5
Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.
Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.
The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.