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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
Copyright © 2020 American Chemical Society

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    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.

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    • 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)

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    Cited By

    This article is cited by 15 publications.

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    2. Haoke Zhang, Ben Zhong Tang. Through-Space Interactions in Clusteroluminescence. JACS Au 2021, 1 (11) , 1805-1814.
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    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.
    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.
    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.
    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.
    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.
    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.
    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.
    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.
    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)
    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.
    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.
    15. Anasuya Mishra, Anshu Kumar, Anil Kumar, Anindya Dutta, , . Aggregation induced enhanced emission in Dimethyl-2,5-bis(4-methoxyphenylamino)terephthalate. 2020, 16.

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