ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Figure 1Loading Img

Structural Chemistry Enables Fluorescence of Amino Acids in the Crystalline Solid State

  • Raheleh Ravanfar
    Raheleh Ravanfar
    Department of Food Science, Cornell University, Ithaca, New York 14853, United States
  • Carol J. Bayles
    Carol J. Bayles
    Department of Biomedical Engineering, Cornell University, Ithaca, New York 14853, United States
  • , and 
  • Alireza Abbaspourrad*
    Alireza Abbaspourrad
    Department of Food Science, Cornell University, Ithaca, New York 14853, United States
    *E-mail for A.A.: [email protected]
Cite this: Cryst. Growth Des. 2020, 20, 3, 1673–1680
Publication Date (Web):January 30, 2020
https://doi.org/10.1021/acs.cgd.9b01430
Copyright © 2020 American Chemical Society

    Article Views

    1156

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (1)»

    Abstract

    Abstract Image

    Nonaromatic luminogens have recently emerged as highly attractive materials for biological imaging and sensing applications, due to their good hydrophilicity and biocompatibility. Here, we report that natural nonaromatic and aromatic amino acids, including l-histidine, l-glutamine, l-isoleucine, l-asparagine, l-valine, l-threonine, and l-methionine, exhibit crystallization-induced emission. The crystalline state of these amino acids shows a wide range of fluorescence emission, in striking contrast to barely any emission in the solution phase. We determined the atomic structure of these amino acids in crystalline state using X-ray crystallography. A structural analysis implies that the compact interactions through the hydrogen-bonding network of the crystallized amino acids potentially restrict intramolecular rotations and vibrations and thus enhance the radiative transitions in the crystalline state. Because these noncovalent interactions can be easily modulated by varying the chemical environment, this phenomenon of crystallization-induced emission may represent a general strategy to induce fluorescence from weakly emissive or nonemissive nonaromatic molecules.

    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. You can change your affiliated institution below.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.cgd.9b01430.

    • Chemical structures of the amino acids, confocal λ scans of amino acid crystals, emission spectra, fluorescence lifetimes, the residuals of fluorescence lifetimes of amino acid crystals, FLIM data of a histidine crystal, crystalline structures of the amino acids, FTIR spectra, XRD spectra, and SEM images of amino acid crystals (PDF)

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 15 publications.

    1. Amrendra Kumar, Shah Ekramul Alom, Dileep Ahari, Anurag Priyadarshi, Mohd. Ziauddin Ansari, Rajaram Swaminathan. Role of Charged Amino Acids in Sullying the Fluorescence of Tryptophan or Conjugated Dansyl Probe in Monomeric Proteins. Biochemistry 2022, 61 (5) , 339-353. https://doi.org/10.1021/acs.biochem.1c00753
    2. Haoke Zhang, Ben Zhong Tang. Through-Space Interactions in Clusteroluminescence. JACS Au 2021, 1 (11) , 1805-1814. https://doi.org/10.1021/jacsau.1c00311
    3. Oktaviana Dewi Indah Prasiwi, Teguh Endah Saraswati, Miftahul Anwar, Abu Masykur. Magnetic Carbon Nanofibers Prepared with Ni and Ni/Graphitic Carbon Nanoparticle Catalysts for Glycine Detection Using Surface-Enhanced Raman Spectroscopy. ACS Applied Nano Materials 2021, 4 (7) , 6594-6608. https://doi.org/10.1021/acsanm.1c00111
    4. Soumya Kanti De, Avijit Maity, Anjan Chakraborty. Underlying Mechanisms for the Modulation of Self-Assembly and the Intrinsic Fluorescent Properties of Amino Acid-Functionalized Gold Nanoparticles. Langmuir 2021, 37 (16) , 5022-5033. https://doi.org/10.1021/acs.langmuir.1c00431
    5. Yingchen Wang, Kai Lin, Wanying Jia, Qiushuo Yu. Measurement and Correlation of Solubility of l-Valine, l-Isoleucine, l-Methionine, and l-Threonine in Water + tert-Butanol from 283.15 to 328.15 K. Journal of Chemical & Engineering Data 2021, 66 (1) , 677-683. https://doi.org/10.1021/acs.jced.0c00821
    6. Roger Bresolí-Obach, José A. Castro-Osma, Santi Nonell, Agustín Lara-Sánchez, Cristina Martín. Polymers showing cluster triggered emission as potential materials in biophotonic applications. Journal of Photochemistry and Photobiology C: Photochemistry Reviews 2024, 58 , 100653. https://doi.org/10.1016/j.jphotochemrev.2024.100653
    7. M. A. Baranov, E. K. Karseeva, O. Yu. Tsybin. Prototypes of Devices for Heterogeneous Hybrid Semiconductor Electronics with an Embedded Biomolecular Domain. Russian Microelectronics 2023, 52 (6) , 517-526. https://doi.org/10.1134/S1063739723700725
    8. Ruth Aizen, Zohar A. Arnon, Or Berger, Antonella Ruggiero, Dor Zaguri, Noam Brown, Evgeny Shirshin, Inna Slutsky, Ehud Gazit. Intrinsic fluorescence of nucleobase crystals. Nanoscale Advances 2023, 5 (2) , 344-348. https://doi.org/10.1039/D2NA00551D
    9. T. V. Sakhno, Yu.E. Sakhno, S. Ya. Kuchmiy. Clusteroluminescence in Organic, Inorganic, and Hybrid Systems: A Review. Theoretical and Experimental Chemistry 2022, 58 (5) , 297-327. https://doi.org/10.1007/s11237-023-09747-8
    10. Mengjiao Yi, Ping Qi, Qi Fan, Jingcheng Hao. Ionic liquid crystals based on amino acids and gemini surfactants: tunable phase structure, circularly polarized luminescence and emission color. Journal of Materials Chemistry C 2022, 10 (5) , 1645-1652. https://doi.org/10.1039/D1TC05265A
    11. Saixing Tang, Tianjia Yang, Zihao Zhao, Tianwen Zhu, Qiang Zhang, Wubeiwen Hou, Wang Zhang Yuan. Nonconventional luminophores: characteristics, advancements and perspectives. Chemical Society Reviews 2021, 50 (22) , 12616-12655. https://doi.org/10.1039/D0CS01087A
    12. Luigi Stagi, Luca Malfatti, Francesca Caboi, Plinio Innocenzi. Thermal Induced Polymerization of l ‐Lysine forms Branched Particles with Blue Fluorescence. Macromolecular Chemistry and Physics 2021, 222 (20) https://doi.org/10.1002/macp.202100242
    13. Yunqian Ma, Hao Zhang, Kexin Wang, Duxia Cao, Kaiming Wang, Ruifang Guan, Chuanjian Zhou. The bright fluorescence of non-aromatic molecules in aqueous solution originates from pH-induced CTE behavior. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2021, 254 , 119604. https://doi.org/10.1016/j.saa.2021.119604
    14. Raheleh Ravanfar, Alireza Abbaspourrad. The molecular mechanism of the photocatalytic oxidation reactions by horseradish peroxidase in the presence of histidine. Green Chemistry 2020, 22 (18) , 6105-6114. https://doi.org/10.1039/D0GC01972K
    15. Anasuya Mishra, Anshu Kumar, Anil Kumar, Anindya Dutta, , . Aggregation induced enhanced emission in Dimethyl-2,5-bis(4-methoxyphenylamino)terephthalate. 2020, 16. https://doi.org/10.1117/12.2548917

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect