Design, Synthesis, and Photovoltaic Performance of Asymmetric Non-fused Ring Electron Acceptors Based on 3-Cyanothiophene

Xue-yan Ding; Tian-yi Chen; Shui-xing Li; Min-min Shi; Hong-zheng Chen

doi:10.11777/j.issn1000-3304.2024.24266

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Design, Synthesis, and Photovoltaic Performance of Asymmetric Non-fused Ring Electron Acceptors Based on 3-Cyanothiophene

Research Article | 更新时间：2025-04-01

- Design, Synthesis, and Photovoltaic Performance of Asymmetric Non-fused Ring Electron Acceptors Based on 3-Cyanothiophene
- Acta Polymerica Sinica Vol. 56, Issue 4, Pages: 515-526(2025)
- 作者机构：
  
  1.浙江大学硅及先进半导体材料全国重点实验室高分子科学与工程学系杭州 310058
  2.浙江大学杭州国际科创中心信息与功能材料研究院杭州 311200
- 作者简介：
  
  Shui-xing Li, E-mail: lishuixing89@zju.edu.cn
  Hong-zheng Chen, E-mail: hzchen@zju.edu.cn
- 基金信息：
- DOI：10.11777/j.issn1000-3304.2024.24266
  CLC：
- CSTR：32057.14.GFZXB.2024.7328
- Received：29 October 2024，
  
  Accepted：2024-12-06，
  
  Published Online：13 February 2025，
  
  Published：20 April 2025
- 稿件说明：
移动端阅览
丁学妍, 陈天一, 李水兴, 施敏敏, 陈红征. 基于3-氰基噻吩的不对称非稠环电子受体材料的设计合成及其光伏性能研究. 高分子学报, 2025, 56(4), 515-526

Ding, X. Y.; Chen, T. Y.; Li, S. X.; Shi, M. M.; Chen, H. Z. Design, synthesis, and photovoltaic performance of asymmetric non-fused ring electron acceptors based on 3-cyanothiophene. Acta Polymerica Sinica, 2025, 56(4), 515-526
丁学妍, 陈天一, 李水兴, 施敏敏, 陈红征. 基于3-氰基噻吩的不对称非稠环电子受体材料的设计合成及其光伏性能研究. 高分子学报, 2025, 56(4), 515-526 DOI： 10.11777/j.issn1000-3304.2024.24266. CSTR： 32057.14.GFZXB.2024.7328.

Ding, X. Y.; Chen, T. Y.; Li, S. X.; Shi, M. M.; Chen, H. Z. Design, synthesis, and photovoltaic performance of asymmetric non-fused ring electron acceptors based on 3-cyanothiophene. Acta Polymerica Sinica, 2025, 56(4), 515-526 DOI： 10.11777/j.issn1000-3304.2024.24266. CSTR： 32057.14.GFZXB.2024.7328.

摘要

建立晶体结构、分子堆积和光伏性能之间的内在联系，对于推动非稠环电子受体材料的发展具有重要意义，而偶极矩是调控分子堆积方式的手段之一. 为此，本研究基于强偶极的3-氰基噻吩构筑单元，开发了一系列不对称非稠环电子受体(X4、X5和X6)，并深入研究了末端基团结构的差异对分子光电特性及有机太阳能电池性能的影响. 氰基的强吸电子性，有效削弱了噻吩的给电子效应，从而使受体保持较深的HOMO能级，与给体材料PM6实现了良好的能级匹配. 单晶结构解析显示，分子中心的强偶极驱使分子采取面对面的二聚体排布，而分子末端的差异化改变了二聚体之间的堆叠方式，其中氟代X4的二聚体之间以J聚集的形式排列，氯代X5的二聚体之间以H聚集和J聚集共存的形式排列. 最终，基于具有更大共轭末端基团的X6制备的器件实现了19.90 mA·cm

-2

的短路电流密度(sho

rt-circuit current density

)、72.38%的填充因子(fill factor

FF)和12.05%的能量转化效率(power conversion efficiency

PCE)，优于X4 (11.81%)和X5 (11.87%)的器件效率.

Abstract

Establishing the intrinsic relationship among crystal structure

molecular packing

and photovoltaic performance is crucial for advancing non-fused ring electron acceptor (NFREA) materials

while dipole moment serves as one of the key factors in regulating molecular packing. In this work

based on the large dipole 3-cyanothiophene building block

a series of asymmetric NFREAs (X4

and X6) were developed

for which the impacts of varied terminal groups on the molecular optoelectronic properties and photovoltaic performance were systematically investigated. The strong electron-withdrawing ability of the cyano-group significantly weakens the electron-donating effect of the thiophene unit

resulting in relatively deep HOMO levels for the acceptors

thus enabling favorable energy level alignment with the donor PM6. Single-crystal analysis revealed that the strong dipole moment at the molecular core drives the dimer formed in face-to-face arrang

ement

while variations in terminal groups alter the stacking arrangements between dimers. Specifically

the fluorinated X4 adopts J-aggregation packing between dimers

while the chlorinated X5 tends to the co-existence of H-aggregation and J-aggregation packing between dimers. Ultimately

organic solar cells based on X6

which bears larger conjugated terminal groups

achieved a short-circuit current density (

) of 19.90 mA·cm

-2

a fill factor (FF) of 72.38%

and a power conversion efficiency (PCE) of 12.05%

outperforming those based on X4 (11.81%) and X5 (11.87%).

关键词

Keywords

references

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