ACS Publications. Most Trusted. Most Cited. Most Read
Near-Infrared, Organic Chiroptic Switch with High Dissymmetry Factors

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Am. Chem. Soc. 2024, 146, 1, 51-56
    Communication

    Near-Infrared, Organic Chiroptic Switch with High Dissymmetry Factors
    Click to copy article linkArticle link copied!

    Other Access OptionsSupporting Information (2)

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2024, 146, 1, 51–56
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.3c10578
    Published December 18, 2023
    Copyright © 2023 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    Here we unveil a chiral molecular redox switch derived from PDI-based twistacenes─chPDI[2] that has the remarkable attributes of high-intensity and a broadband chiral response. This material exhibits facile, stable, and reversible multistate chiroptical switching behavior over a broad active wavelength range close to 700 nm, encompassing ultraviolet, visible, and near-infrared regions. Upon reduction, chPDI[2] exhibits a substantial increase in the amplitude of its circular dichroic response, with an outstanding |ΔΔε| > 300 M–1 cm–1 and a high dissymmetry factor of 3 × 10–2 at 960 nm. DFT calculations suggest that the long wavelength CD signal for doubly reduced chPDI[2] originates from excitation of the PDI backbone to the π* orbital of the bridging alkene. Importantly, the dimer’s molecular contortion facilitates ionic diffusion, enabling chiral switching in solid state films. The high dissymmetry factors and near-infrared response establish chPDI[2] as a unique chiroptic switch.

    Copyright © 2023 American Chemical Society

    Subjects

    what are subjects

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.3c10578.

    • Synthetic details and characterization, 1H NMR studies, 13C NMR studies, EPR studies, electrochemical data, and calculation details (PDF)

    • Film color change between chPDI[2] and chPDI[2]2– on an ITO coated glass slide (MP4)

    Terms & Conditions

    Electronic Supporting Information files are available without a subscription to ACS Web Editions. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Information. Files available from the ACS website may be downloaded for personal use only. Users are not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information from the ACS website, either in whole or in part, in either machine-readable form or any other form without permission from the American Chemical Society. For permission to reproduce, republish and redistribute this material, requesters must process their own requests via the RightsLink permission system. Information about how to use the RightsLink permission system can be found at http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai
    powered by  Scite

    This article is cited by 15 publications.

    1. Haoyu Jiang, Daniel Čavlović, Qifeng Jiang, Fay Ng, Si Tong Bao, Evan J. Telford, Michael L. Steigerwald, Xavier Roy, Colin Nuckolls, Jeffrey M. McNeill. Spin Filtering with Surface-Active Helicene- and Twistacene-Based Perylene Diimides. Journal of the American Chemical Society 2025, 147 (15) , 12982-12988. https://doi.org/10.1021/jacs.5c02723
    2. Abdusalom A. Suleymanov, Yucheng Fu, Peter Müller, Timothy M. Swager. Azacoronene in Helicenes and Conjugated Polymers. Organic Letters 2025, 27 (13) , 3150-3153. https://doi.org/10.1021/acs.orglett.5c00398
    3. Lyndon A. Hall, Hunter J. Windsor, Bun Chan, Deanna M. D’Alessandro, Girish Lakhwani. Chiroptical Switching in an Enantiomeric Pair of Binaphthylenes Based on Redox-Active 1,8-Naphthalimide Substituents. The Journal of Physical Chemistry Letters 2025, 16 (6) , 1529-1534. https://doi.org/10.1021/acs.jpclett.4c03120
    4. Kai Chen, Yujian Liu, Zhaolong Wang, Shunlong Hu, Yilun Zhao, Wei Wang, Guogang Liu, Zhaohui Wang, Wei Jiang. Longitudinal Extension of Double π-Helix Enables Near-Infrared Amplified Dissymmetry and Chiroptical Response. Journal of the American Chemical Society 2024, 146 (19) , 13499-13508. https://doi.org/10.1021/jacs.4c02914
    5. Pingyu Jiang, Alexander S. Mikherdov, Hajime Ito, Mingoo Jin. Crystallization-Induced Chirality Transfer in Conformationally Flexible Azahelicene Au(I) Complexes with Circularly Polarized Luminescence Activation. Journal of the American Chemical Society 2024, 146 (18) , 12463-12472. https://doi.org/10.1021/jacs.4c00345
    6. Si Tong Bao, Qifeng Jiang, Haoyu Jiang, Daniel Čavlović, Colin Nuckolls. Chiral Materials from Twistacenes and Helicenes. 2025, 381-395. https://doi.org/10.1002/9783527845019.ch17
    7. Shayan Louie, Qifeng Jiang, Duncan J. Wisniewski, Si Tong Bao, Honghu Zhang, Kaushik Chivukula, Qiyi Fang, Ashutosh Garudapalli, Scott R. Docherty, Fay Ng, Michael Steigerwald, Yu Zhong, Dion Khodagholy, Colin Nuckolls. Contorted acene ribbons for stable and ultrasensitive neural probes. Science Advances 2025, 11 (14) https://doi.org/10.1126/sciadv.adu2356
    8. Jie Yu, Huijia Yu, Yugui Qiu, Heng‐Yi Zhang, Xiufang Xu, Yu Liu. Biofuel‐Driven Stepping Chiral Supramolecular Transfer Container. Angewandte Chemie International Edition 2025, 64 (5) https://doi.org/10.1002/anie.202418938
    9. Jie Yu, Huijia Yu, Yugui Qiu, Heng‐Yi Zhang, Xiufang Xu, Yu Liu. Biofuel‐Driven Stepping Chiral Supramolecular Transfer Container. Angewandte Chemie 2025, 137 (5) https://doi.org/10.1002/ange.202418938
    10. Takashi Harimoto, Yusuke Ishigaki. Recent Advances in NIR‐Switchable Multi‐Redox Systems Based on Organic Molecules. Chemistry – A European Journal 2025, 31 (3) https://doi.org/10.1002/chem.202403273
    11. Max Coehlo, Lucas Frédéric, Laurélie Poulard, Nawal Ferdi, Lilian Estaque, Alaric Desmarchelier, Gilles Clavier, Jean‐Pierre Dognon, Ludovic Favereau, Michel Giorgi, Jean‐Valère Naubron, Gregory Pieters. Control of Dynamic Chirality in Donor‐Acceptor Fluorophores. Angewandte Chemie 2025, 137 (2) https://doi.org/10.1002/ange.202414490
    12. Max Coehlo, Lucas Frédéric, Laurélie Poulard, Nawal Ferdi, Lilian Estaque, Alaric Desmarchelier, Gilles Clavier, Jean‐Pierre Dognon, Ludovic Favereau, Michel Giorgi, Jean‐Valère Naubron, Gregory Pieters. Control of Dynamic Chirality in Donor‐Acceptor Fluorophores. Angewandte Chemie International Edition 2025, 64 (2) https://doi.org/10.1002/anie.202414490
    13. Kouzou Matsumoto, Rina Tanaka, Kaori Miki, Akihito Konishi, Hiroyuki Kurata, Takashi Kubo, Gennaro Pescitelli, Koichi Matsuo, Tatsuo Nehira. Synthesis, Chiroptical Properties, and Absolute Configuration Determination of Phenyl‐4‐pyridyl‐2,5‐dipyrimidinylmethane. Asian Journal of Organic Chemistry 2025, 14 (1) https://doi.org/10.1002/ajoc.202400577
    14. Zhiyu Zhang, Yoshifumi Hashikawa, Chaolumen. Chemical oxidation of a double-twisted nanographene. Chemical Communications 2024, 60 (94) , 13875-13878. https://doi.org/10.1039/D4CC05264A
    15. Junichiro Hirano, Sayaka Miyoshi, Eiji Yashima, Tomoyuki Ikai, Hiroshi Shinokubo, Norihito Fukui. Synthesis of sterically congested double helicene by alkyne cycloisomerization. Chemical Communications 2024, 60 (47) , 6035-6038. https://doi.org/10.1039/D4CC01573H
    Download PDF
    Go to Journal of the American Chemical Society
    Get e-Alerts
    Get e-Alerts

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2024, 146, 1, 51–56
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.3c10578
    Published December 18, 2023
    Copyright © 2023 American Chemical Society
    Request reuse permissions

    Article Views

    4246

    Altmetric

    -

    Citations

    15
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.