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Prevalent intrinsic emission from nonaromatic amino acids and poly(amino acids)

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Abstract

Nonaromatic amino acids are generally believed to be nonemissive, owing to their lack of apparently remarkable conjugation within individual molecules. Here we report the intrinsic visible emission of nonaromatic amino acids and poly(amino acids) in concentrated solutions and solid powders. This unique and widespread luminescent characteristic can be well rationalized by the clustering-triggered emission (CTE) mechanism, namely the clustering of nonconventional chromophores (i.e. amino, carbonyl, and hydroxyl) and subsequent electron cloud overlap with simultaneous conformation rigidification. Such CTE mechanism is further supported by the single crystal structure analysis, from which 3D through space electronic communications are uncovered. Besides prompt fluorescence, room temperature phosphorescence (RTP) is also detected from the solids. Moreover, persistent RTP is observed in the powders of exampled poly(amino acids) of ε-poly-L-lysine (ɛ-PLL) after ceasing UV irradiation. These results not only illustrate the feasibility of employing the building blocks of nonaromatic amino acids in the exploration of new luminescent biomolecules, but also provide significant implications for the emissions of peptides and proteins at aggregated or crystalline states. Meanwhile, they may also shed lights on further understanding of autofluorescence from biological systems.

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Acknowledgments

This work was supported by the National Natural Science Foundation of China (51473092), and the Shanghai Rising-Star Program (15QA1402500). The authors appreciate Ms Xiaoli Bao and Ms Lingling Li at the Instrumental Analysis Center of Shanghai Jiao Tong University for the single-crystal structure determination of L-Ile.

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Shanghai Key Laboratory of Electrical Insulation and Thermal Aging, Shanghai Electrochemical Energy Devices Research Center, Shanghai Jiao Tong University, Shanghai, 200240, China

    Xiaohong Chen, Weijian Luo, Wang Zhang Yuan & Yongming Zhang

  2. Department of Chemistry, Tsinghua University, Beijing, 100084, China

    Huili Ma

  3. Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China

    Qian Peng

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  1. Xiaohong Chen
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  2. Weijian Luo
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Correspondence to Wang Zhang Yuan or Yongming Zhang.

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Chen, X., Luo, W., Ma, H. et al. Prevalent intrinsic emission from nonaromatic amino acids and poly(amino acids). Sci. China Chem. 61, 351–359 (2018). https://doi.org/10.1007/s11426-017-9114-4

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  • DOI: https://doi.org/10.1007/s11426-017-9114-4

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