π-Truncation of a Parent Nanographene: Chirally Twisted Green Fluorophores

The twist operation of the π-skeleton would induce left or right handedness. Herein, we report two chirally twisted C<sub>64</sub> nanographenes designed by formally erasing two fused benzenes from a parent C<sub>76</sub> nanographene. These C<sub>64</sub> nanographenes possess two [6]helical units implemented around a central pyrene core in a different arrangement. The π-truncation pulls the emission bands hypsochromically from the red (C<sub>76</sub>, λ<sub>max</sub> = 612 nm) to green (C<sub>64</sub>, λ<sub>max</sub> = 505 and 506 nm) region. Curiously, the +/- sign of circularly polarized luminescence at the S<sub>1</sub> → S<sub>0</sub> transition was reversed between the two C<sub>64</sub> nanographenes despite them possessing the same handedness. This is attributed to the slight difference in the arrangement of the two transition dipole moments fluctuating at around 90°, as suggested computationally.

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Publication Details

Journal
Organic Letters
Published
2025-06-18
DOI
https://doi.org/10.1021/acs.orglett.5c01902
Citations
2
Primary Topic
Synthesis and Properties of Aromatic Compounds
Type
article
Field-Weighted Citation Impact
1.87

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article

π-Truncation of a Parent Nanographene: Chirally Twisted Green Fluorophores

Ziqiang Xu, Huricha Baigude, Shuqin Han, Chaolumen Chaolumen et al.
2 citations
Organic Letters
Synthesis and Properties of Aromatic Compounds
1.87
article

π-Truncation of a Parent Nanographene: Chirally Twisted Green Fluorophores

Ziqiang Xu, Huricha Baigude, Shuqin Han, Chaolumen Chaolumen, Yoshifumi Hashikawa, Meng He, Tianyu Zhang
article en
2 citations

Abstract

The twist operation of the π-skeleton would induce left or right handedness. Herein, we report two chirally twisted C<sub>64</sub> nanographenes designed by formally erasing two fused benzenes from a parent C<sub>76</sub> nanographene. These C<sub>64</sub> nanographenes possess two [6]helical units implemented around a central pyrene core in a different arrangement. The π-truncation pulls the emission bands hypsochromically from the red (C<sub>76</sub>, λ<sub>max</sub> = 612 nm) to green (C<sub>64</sub>, λ<sub>max</sub> = 505 and 506 nm) region. Curiously, the +/- sign of circularly polarized luminescence at the S<sub>1</sub> → S<sub>0</sub> transition was reversed between the two C<sub>64</sub> nanographenes despite them possessing the same handedness. This is attributed to the slight difference in the arrangement of the two transition dipole moments fluctuating at around 90°, as suggested computationally.

Organic LettersVol. 27(26)
Kyoto University (JP), Inner Mongolia University (CN), Kyoto Bunkyo University (JP), Kyoto University Institute for Chemical Research
Asahi Glass Foundation, Takahashi Industrial and Economic Research Foundation, Japan Association for Chemical Innovation, Education Department of Inner Mongolia Autonomous Region, National Natural Science Foundation of China, Yazaki Memorial Foundation for Science and Technology, Institute for Chemical Research, Kyoto University
Openalex Percentile: Top 15%
Synthesis and Properties of Aromatic Compounds
1.87
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π-Truncation of a Parent Nanographene: Chirally Twisted Green Fluorophores — Ziqiang Xu, Huricha Baigude, et al. · Organic Letters (2025) | TGRS Research Map | TGRS