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Download Hi-Res ImageDownload to MS-PowerPointCite This:ACS Appl. Mater. Interfaces 2022, 14, 18, 20790-20801
    Biological and Medical Applications of Materials and Interfaces

    Hydroporphyrin-Doped Near-Infrared-Emitting Polymer Dots for Cellular Fluorescence Imaging
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    • Connor Riahin
      Connor Riahin
      Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, Maryland 21250, United States
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    • Adam Meares
      Adam Meares
      Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, Maryland 21250, United States
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    • Nopondo N. Esemoto
      Nopondo N. Esemoto
      Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, Maryland 21250, United States
      More by Nopondo N. Esemoto
      Orcidhttps://orcid.org/0000-0001-5212-4484
    • Marcin Ptaszek
      Marcin Ptaszek
      Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, Maryland 21250, United States
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      Orcidhttps://orcid.org/0000-0001-6468-6900
    • Michael LaScola
      Michael LaScola
      Department of Chemical, Biological and Environmental Engineering, University of Maryland, Baltimore County, Baltimore, Maryland 21250, United States
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    • Narendra Pandala
      Narendra Pandala
      Department of Chemical, Biological and Environmental Engineering, University of Maryland, Baltimore County, Baltimore, Maryland 21250, United States
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    • Erin Lavik
      Erin Lavik
      Department of Chemical, Biological and Environmental Engineering, University of Maryland, Baltimore County, Baltimore, Maryland 21250, United States
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      Orcidhttps://orcid.org/0000-0002-0644-744X
    • Mengran Yang
      Mengran Yang
      Division of Plant Sciences and Biochemistry, University of Missouri, Columbia, Missouri 65211, United States
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    • Gary Stacey
      Gary Stacey
      Division of Plant Sciences and Biochemistry, University of Missouri, Columbia, Missouri 65211, United States
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    • Dehong Hu
      Dehong Hu
      Environmental Molecular Sciences Laboratory, Pacific Northwest National Laboratory, Richland, Washington 99354, United States
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      Orcidhttps://orcid.org/0000-0002-3974-2963
    • Jeremiah C. Traeger
      Jeremiah C. Traeger
      Environmental Molecular Sciences Laboratory, Pacific Northwest National Laboratory, Richland, Washington 99354, United States
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    • Galya Orr
      Galya Orr
      Environmental Molecular Sciences Laboratory, Pacific Northwest National Laboratory, Richland, Washington 99354, United States
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      Orcidhttps://orcid.org/0000-0002-5552-2151
    • Zeev Rosenzweig*
      Zeev Rosenzweig
      Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, Maryland 21250, United States
      *Email: [email protected]
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      Orcidhttps://orcid.org/0000-0001-6098-3932
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    ACS Applied Materials & Interfaces

    Cite this: ACS Appl. Mater. Interfaces 2022, 14, 18, 20790–20801
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    https://doi.org/10.1021/acsami.2c02551
    Published April 22, 2022
    Copyright © 2022 American Chemical Society
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    Abstract

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    Near-infrared (NIR) fluorescent semiconductor polymer dots (Pdots) have shown great potential for fluorescence imaging due to their exceptional chemical and photophysical properties. This paper describes the synthesis of NIR-emitting Pdots with great control and tunability of emission peak wavelength. The Pdots were prepared by doping poly[(9,9-dioctylfluorenyl-2,7-diyl)-alt-co-(1,4-benzo-(2,1′,3)-thiadiazole)] (PFBT), a semiconducting polymer commonly used as a host polymer in luminescent Pdots, with a series of chlorins and bacteriochlorins with varying functional groups. Chlorins and bacteriochlorins are ideal dopants due to their high hydrophobicity, which precludes their use as molecular probes in aqueous biological media but on the other hand prevents their leakage when doped into Pdots. Additionally, chlorins and bacteriochlorins have narrow deep red to NIR-emission bands and the wide array of synthetic modifications available for modifying their molecular structure enables tuning their emission predictably and systematically. Transmission electron microscopy (TEM) and dynamic light scattering (DLS) measurements show the chlorin- and bacteriochlorin-doped Pdots to be nearly spherical with an average diameter of 46 ± 12 nm. Efficient energy transfer between PFBT and the doped chlorins or bacteriochlorins decreases the PFBT donor emission to near baseline level and increases the emission of the doped dyes that serve as acceptors. The chlorin- and bacteriochlorin-doped Pdots show narrow emission bands ranging from 640 to 820 nm depending on the doped dye. The paper demonstrates the utility of the systematic chlorin and bacteriochlorin synthesis approach by preparing Pdots of varying emission peak wavelength, utilizing them to visualize multiple targets using wide-field fluorescence microscopy, binding them to secondary antibodies, and determining the binding of secondary antibody-conjugated Pdots to primary antibody-labeled receptors in plant cells. Additionally, the chlorin- and bacteriochlorin-doped Pdots show a blinking behavior that could enable their use in super-resolution imaging methods like STORM.

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsami.2c02551.

    • Detailed information about the synthesis and characterization of bacteriochlorin P790 (Scheme S1 and Section 1.1), the absorption and emission spectra of the chlorin and bacteriochlorin dyes used in the study (Figures S1–S6 in Section 1.2), and ζ-potential of the Pdots (Figure S7 in Section 1.3) (PDF)

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    Cited By

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    This article is cited by 3 publications.

    1. Carl C. Wamser, Abhik Ghosh. The Hyperporphyrin Concept: A Contemporary Perspective. JACS Au 2022, 2 (7) , 1543-1560. https://doi.org/10.1021/jacsau.2c00255
    2. Sile Deng, Lingfeng Li, Jiaxi Zhang, Yongjun Wang, Zhongchao Huang, Haobin Chen. Semiconducting Polymer Dots for Point-of-Care Biosensing and In Vivo Bioimaging: A Concise Review. Biosensors 2023, 13 (1) , 137. https://doi.org/10.3390/bios13010137
    3. Connor Riahin, Kushani Mendis, Brandon Busick, Marcin Ptaszek, Mengran Yang, Gary Stacey, Amar Parvate, James E. Evans, Jeremiah Traeger, Dehong Hu, Galya Orr, Zeev Rosenzweig. Near Infrared Emitting Semiconductor Polymer Dots for Bioimaging and Sensing. Sensors 2022, 22 (19) , 7218. https://doi.org/10.3390/s22197218
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    ACS Applied Materials & Interfaces

    Cite this: ACS Appl. Mater. Interfaces 2022, 14, 18, 20790–20801
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acsami.2c02551
    Published April 22, 2022
    Copyright © 2022 American Chemical Society
    Request reuse permissions

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