Volume 63, Issue 41 e202409713
Research Article

The Effects of Pore Defects in π-Extended Pentadecabenzo[9]helicene

Ke-Lin Zhu

Ke-Lin Zhu

College of Chemistry, Beijing Normal University, No. 19, XinWai St, HaiDian District, Beijing, 100875 China

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Zhi-Ao Li

Zhi-Ao Li

College of Chemistry, Beijing Normal University, No. 19, XinWai St, HaiDian District, Beijing, 100875 China

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Dr. Jiaqi Liang

Dr. Jiaqi Liang

College of Chemistry, Beijing Normal University, No. 19, XinWai St, HaiDian District, Beijing, 100875 China

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Kang-Li Zou

Kang-Li Zou

College of Chemistry, Beijing Normal University, No. 19, XinWai St, HaiDian District, Beijing, 100875 China

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Dr. Yun-Jia Shen

Dr. Yun-Jia Shen

College of Chemistry, Beijing Normal University, No. 19, XinWai St, HaiDian District, Beijing, 100875 China

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Prof. Han-Yuan Gong

Corresponding Author

Prof. Han-Yuan Gong

College of Chemistry, Beijing Normal University, No. 19, XinWai St, HaiDian District, Beijing, 100875 China

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First published: 19 July 2024
Citations: 6

Graphical Abstract

A bottom-up synthesis strategy was used to introduce pore defects into the fully conjugated π-extended helicene. This modification transformed the helicene with original aggregation-caused quenching (ACQ) characteristics into a series of novel helicenes with dual-state emission (DSE) and circularly polarized luminescence (CPL) properties. Consequently, the application range of the helicene in chiral luminescent materials was expanded.

Abstract

The introduction of precise pore defects into nanocarbon structures results in the emergence of distinct physicochemical characteristics. However, there is a lack of research on non-planar chiral nanographene involving precise pore defects. Herein, we have developed two analogues to the π-extended pentadecabenzo[9]helicene (EP9H) containing embedded pore defects. Each molecules, namely extended dodecabenzo[7]helicene (ED7H; 1) or extended nonabenzo[5]helicene (EN5H; 2), exhibits dual-state emission. Significantly, the value of |glum| of 1 is exceptionally high at 1.41×10−2 in solution and BCPL as 254 M−1 cm−1. In PMMA film, |glum| of 1 is 8.56×10−3, and in powder film, it is 5.00×10−3. This study demonstrates that nanocarbon molecules with pore defects exhibit dual-state emission properties while maintaining quite good chiral luminescence properties. It was distinguished from the aggregation-caused quenching (ACQ) effect corresponding to the nanocarbon without embedded defect. Incorporating pore defects into chiral nanocarbon molecules also simplifies the synthesis process and enhances the solubility of the resulting product. These findings suggest that the introduction of pore defects can be a viable approach to improve nanocarbon molecules.

Conflict of Interests

The authors declare no conflict of interest.

Data Availability Statement

The data that support the findings of this study are available in the supplementary material of this article.

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