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<p>Helicene-based materials hold substantial promise for circularly polarized light (CPL) detection owing to their large absorption asymmetry factors (<i>g</i><sub>abs</sub>). However, their synthesis and chiral resolution remain experimentally challenging. Herein, we synthesized a pair of diastereoisomers: (<i>SSSS</i>)-diPDI-(<i>S</i>)-MP and (<i>SSSS</i>)-diPDI-(<i>R</i>)-MP, through synergistic chiral induction at both the imide and bay positions. Density functional theory (DFT) calculations reveal that these (<i>SSSS</i>)-diPDI-(<i>S</i>)-MP and (<i>SSSS</i>)-diPDI-(<i>R</i>)-MP exhibit distinct angles between their electric and magnetic transition dipoles (130° and 61°, respectively), which gives rise to opposite <i>g</i><sub>abs</sub> signals. The agreement between the simulated circular dichroism (CD) and the experimental data in the monomeric state further confirms that (<i>SSSS</i>)-diPDI-(<i>S</i>)-MP possesses an M-configuration and (<i>SSSS</i>)-diPDI-(<i>R</i>)-MP possesses a <i>P</i>-configuration. Thin film-based organic phototransistors (OPTs) fabricated using (<i>SSSS</i>)-diPDI-(<i>S</i>)-MP and (<i>SSSS</i>)-diPDI-(<i>R</i>)-MP also exhibit opposite photocurrent asymmetry factors (<i>g</i><sub>ph</sub>) of −0.26 and 0.25, respectively. Besides, the OPTs based on (<i>SSSS</i>)-diPDI-(<i>R</i>)-MP thin films enable sensitive CPL imaging application. Notably, this study not only presents a novel strategy for synthesizing helicene-based materials without the need for chiral resolution but also provides critical insights for the development of chiral optoelectronics.</p>

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Synergistic chiral induction within diperylene diimide diastereoisomers for high-performance circularly polarized light detection

  • 期刊论文

  • 发表日期：

    2026年3月19日

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  • Jinhang Liu,
  • Chao Zhang,
  • Lixuan Liu,
  • Wenkai Zhao,
  • Lei Ma,
  • Ke Gao,
  • Zhiwei Wang,
  • Zhenping Li,
  • Huagui Zhuo,
  • Zhuofan Wang,
  • Gang Chang,
  • Yuchen Wu,
  • Hanfei Gao,
  • Guankui Long,
  • Xiaobo Shang,
  • Wei Ma

摘要

Helicene-based materials hold substantial promise for circularly polarized light (CPL) detection owing to their large absorption asymmetry factors (gabs). However, their synthesis and chiral resolution remain experimentally challenging. Herein, we synthesized a pair of diastereoisomers: (SSSS)-diPDI-(S)-MP and (SSSS)-diPDI-(R)-MP, through synergistic chiral induction at both the imide and bay positions. Density functional theory (DFT) calculations reveal that these (SSSS)-diPDI-(S)-MP and (SSSS)-diPDI-(R)-MP exhibit distinct angles between their electric and magnetic transition dipoles (130° and 61°, respectively), which gives rise to opposite gabs signals. The agreement between the simulated circular dichroism (CD) and the experimental data in the monomeric state further confirms that (SSSS)-diPDI-(S)-MP possesses an M-configuration and (SSSS)-diPDI-(R)-MP possesses a P-configuration. Thin film-based organic phototransistors (OPTs) fabricated using (SSSS)-diPDI-(S)-MP and (SSSS)-diPDI-(R)-MP also exhibit opposite photocurrent asymmetry factors (gph) of −0.26 and 0.25, respectively. Besides, the OPTs based on (SSSS)-diPDI-(R)-MP thin films enable sensitive CPL imaging application. Notably, this study not only presents a novel strategy for synthesizing helicene-based materials without the need for chiral resolution but also provides critical insights for the development of chiral optoelectronics.