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Reversible coloring/decoloring reactions of thermochromic leuco dyes controlled by a macrocyclic compound developer

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Abstract

In this study, we examine macrocyclic compounds to determine whether they can provide a safer replacement and stable complex for BPA in thermochromic dyes. To achieve this objective, a series of macrocyclic compounds, Methyl-N-benzylhexahomotriazacalix[3]arene (MeAC3), p-Chloro-N-benzylhexahomo-triazacalix[3]arene (ClAC3), α-Cyclodexdrin (α-CD), β-Cyclodexdrin (β-CD), p-tert-Butylthiacalix[4]arene (TC4), Calix[4]arene (C4), and Resorcin[4]arene (RC4), were synthesized. Among these macrocyclic compounds, RC4 was determined to be the most appropriate candidate to replace BPA as the developer material used in thermochromic dyes. In tests of prepared thermochromic dyes, RC4 had results similar to those of BPA, achieving the best protonation/deprotonation equilibria and providing a dark contrast with the thermochromic dye. DFT calculations also showed stable complexes between RC4 and CVL via hydrogen-bond interactions.

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Funding

This research project was financially supported by Mahasarakham University 2021 and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Office of the Higher Education Commission, Ministry of Education. This research work also was partially supported by Chiang Mai University and the Graduate School, Chiang Mai University.

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Authors and Affiliations

  1. Department of Industrial Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand

    Sanguansak Sriphalang & Datchanee Pattavarakorn

  2. Graduate School, Chiang Mai University, Chiang Mai, 50200, Thailand

    Sanguansak Sriphalang

  3. Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Srinakharinwirot University, Bangkok, 10110, Thailand

    Audchara Saenkham

  4. Center of Excellence in Materials Science and Technology, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand

    Datchanee Pattavarakorn

  5. Nanotechnology Research Unit and Supramolecular Chemistry Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahasarakham University, Mahasarakham, 44150, Thailand

    Tawatchai Chaodongbung, Banchob Wanno & Chatthai Kaewtong

Authors
  1. Sanguansak Sriphalang
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  2. Audchara Saenkham
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  3. Tawatchai Chaodongbung
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  4. Banchob Wanno
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  5. Chatthai Kaewtong
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  6. Datchanee Pattavarakorn
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Contributions

S. Sriphalang, C. Kaewtong, and D. Pattavarakorn contributed to the study conception and design. The DFT calculations were performed by S. Sriphalang and B. Wanno. The experimental procedures were performed by S. Sriphalang, A. Saenkham, T. Chaodongbung, C. Kaewtong, and D. Pattavarakorn. The data analysis and the first draft of the manuscript were made by S. Sriphalang, C. Kaewtong, D. Pattavarakorn, and B. Wanno. Revising the manuscript critically for important intellectual content on subsequent versions of the manuscript has been done by S. Sriphalang, A. Saenkham, T. Chaodongbung, C. Kaewtong, and D. Pattavarakorn. All the authors read and approved the final manuscript.

Corresponding authors

Correspondence to Chatthai Kaewtong or Datchanee Pattavarakorn.

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The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

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Sriphalang, S., Saenkham, A., Chaodongbung, T. et al. Reversible coloring/decoloring reactions of thermochromic leuco dyes controlled by a macrocyclic compound developer. Struct Chem 33, 1085–1095 (2022). https://doi.org/10.1007/s11224-022-01922-2

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  • DOI: https://doi.org/10.1007/s11224-022-01922-2

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