π‐Extended Heli(aminoborane)s with Highly Bright Circularly Polarized Luminescence and Narrowband Emission

Helical molecular carbons (HMCs) possess high absorption/luminescence dissymmetry factors (g<sub>abs</sub>/g<sub>lum</sub>) and significant luminescence quantum yield (Φ<sub>lum</sub>), resulting in a high circularly polarized luminescence (CPL) brightness (B<sub>CPL</sub>), which is essential for the development of CPL materials for practical applications. Herein, we designed and synthesized a series of boron-nitrogen (BN)-doped HMCs, named π-extended heli(aminoborane)s (E[10]HAB-A, E[10]HAB-B and E[10]HAB-C), consisting of laterally π-extended [10]helicene skeleton with alternating N and B atoms at the inner rim. The aromaticity, electronic structures, and photophysical properties of E[10]HAB-A/B/C were systematically investigated through experiments and theoretical calculations. E[10]HAB-A/B/C displayed remarkable photophysical properties, including high molar extinction coefficient and bright narrowband emission. The isolated enantiomers of E[10]HAB-A/B/C exhibited intense circular dichroism (CD) and CPL, in which E[10]HAB-A shows g<sub>abs</sub> and g<sub>lum</sub> values up to 0.024 and 0.017, simultaneously with high Φ<sub>lum</sub> of 82 % and a narrow full width at half maximum of 16 nm. Accordingly, E[10]HAB-A exhibits a B<sub>CPL</sub> as high as 583 M<sup>-1</sup> cm<sup>-1</sup>, which is the largest value among the reported BN-doped HMCs. Our study indicates that inner rim BN-doping and π-extension are effective strategies to achieve high Φ<sub>lum</sub> and balanced g<sub>lum</sub> values in HMCs.

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Publication Details

Journal
Angewandte Chemie International Edition
Published
2025-02-20
DOI
https://doi.org/10.1002/anie.202501645
Citations
26
Primary Topic
Synthesis and Properties of Aromatic Compounds
Type
article
Field-Weighted Citation Impact
24.34

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article

π‐Extended Heli(aminoborane)s with Highly Bright Circularly Polarized Luminescence and Narrowband Emission

Long Jiang, Faan-Fung Hung, Junzhi Liu, Chi‐Ming Che et al.
26 citations
Angewandte Chemie International Edition
Synthesis and Properties of Aromatic Compounds
24.34
article

π‐Extended Heli(aminoborane)s with Highly Bright Circularly Polarized Luminescence and Narrowband Emission

Long Jiang, Faan-Fung Hung, Junzhi Liu, Chi‐Ming Che, Chang Wang, Yang Yu
article en
26 citations

Abstract

Helical molecular carbons (HMCs) possess high absorption/luminescence dissymmetry factors (g<sub>abs</sub>/g<sub>lum</sub>) and significant luminescence quantum yield (Φ<sub>lum</sub>), resulting in a high circularly polarized luminescence (CPL) brightness (B<sub>CPL</sub>), which is essential for the development of CPL materials for practical applications. Herein, we designed and synthesized a series of boron-nitrogen (BN)-doped HMCs, named π-extended heli(aminoborane)s (E[10]HAB-A, E[10]HAB-B and E[10]HAB-C), consisting of laterally π-extended [10]helicene skeleton with alternating N and B atoms at the inner rim. The aromaticity, electronic structures, and photophysical properties of E[10]HAB-A/B/C were systematically investigated through experiments and theoretical calculations. E[10]HAB-A/B/C displayed remarkable photophysical properties, including high molar extinction coefficient and bright narrowband emission. The isolated enantiomers of E[10]HAB-A/B/C exhibited intense circular dichroism (CD) and CPL, in which E[10]HAB-A shows g<sub>abs</sub> and g<sub>lum</sub> values up to 0.024 and 0.017, simultaneously with high Φ<sub>lum</sub> of 82 % and a narrow full width at half maximum of 16 nm. Accordingly, E[10]HAB-A exhibits a B<sub>CPL</sub> as high as 583 M<sup>-1</sup> cm<sup>-1</sup>, which is the largest value among the reported BN-doped HMCs. Our study indicates that inner rim BN-doping and π-extension are effective strategies to achieve high Φ<sub>lum</sub> and balanced g<sub>lum</sub> values in HMCs.

Angewandte Chemie International EditionVol. 64(18)
Sun Yat-sen University (CN), Chinese University of Hong Kong (HK), State Key Laboratory of Synthetic Chemistry (CN), Institut de Recherche et d’Innovation (FR), University of Hong Kong (HK)
National Natural Science Foundation of China, Chinese Academy of Sciences, Innovation and Technology Commission, University of Hong Kong
Openalex Percentile: Top 0%
Synthesis and Properties of Aromatic Compounds
24.34
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