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Influences of molecular structures on the spectral properties and photostability of rhodamine dyes

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Abstract

Although the syntheses and applications of rhodamine dyes have been extensively researched, their photophysical properties and photostability have rarely been studied. In this study, we systematically investigated the photophysical properties and photostability of six rhodamine dyes by the spectrum measurements, photodegradation experiments and theoretical calculations. It was found that the following structural modifications can lead to the redshift of absorption and fluorescence emission spectra: increasing the alkyls of amino on xanthene; forming rigid ring between the N-linked alkyl and xanthene; and esterification of –COOH on benzene ring. The degradation experiments under 525-nm light irradiation indicated that increasing the alkyls of amino on xanthene improves the photostability, fixing the N-linked alkyls on the xanthene ring to form rigid rings significantly reduces the photostability of rhodamine dyes, and the esterification of –COOH on benzene ring can increase their photostability to some extent. The results of DFT calculations showed that the esterification of –COOH decreases the dihedral angle D1 and increases D2, the variation trends of calculated absorption and emission wavelengths are consistent with the measured results, and the rhodamine dyes with higher electrophilic index usually have higher photostability.

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Acknowledgements

All authors gratefully acknowledge the support of Science and Technology on Particle Transport and Separation Laboratory.

Funding

This research was funded by the Shanghai Industrial Collaborative Innovation Project (XTCX-KJ-2022-2-01), the Science and Technology Commission of Shanghai Municipality (20DZ2250400), the National Natural Science Foundation of China (U1862112), and the Fundamental Research Funds for the Central Universities (JKD01211701, 222201717003, 50321041917001, 50321042017001).

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Authors and Affiliations

  1. Shanghai Engineering Research Center for Multi-Media Environmental Catalysis and Resource Utilization, Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, Key Laboratory of Specially Functional Polymeric Materials and Related Technology (Ministry of Education), School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, People’s Republic of China

    Yudong Liu, Fan Chen, Jinlong Zhang & Baozhu Tian

  2. Research Institute of Physical and Chemical Engineering of Nuclear Industry, 168 Jintang Road, Tianjin, 300180, People’s Republic of China

    Yudong Liu, Liang Sun, Zhizhong Zhang & Shunzhou Chang

Authors
  1. Yudong Liu
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  2. Fan Chen
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  3. Liang Sun
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  4. Zhizhong Zhang
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  5. Shunzhou Chang
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  6. Jinlong Zhang
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  7. Baozhu Tian
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Contributions

FC and YDL did the experiments; LS, SZC, and ZZZ analyzed the data; YDL and BZT wrote the manuscript; JLZ revised the manuscript. All authors reviewed the manuscript.

Corresponding authors

Correspondence to Jinlong Zhang or Baozhu Tian.

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Liu, Y., Chen, F., Sun, L. et al. Influences of molecular structures on the spectral properties and photostability of rhodamine dyes. Res Chem Intermed 49, 2417–2432 (2023). https://doi.org/10.1007/s11164-023-05016-4

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