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Triarylmethane Mechanophores Enable Full-Visible Spectrum Mechanochromism

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Download Hi-Res ImageDownload to MS-PowerPointCite This:Macromolecules 2023, 56, 21, 8614-8622
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    Triarylmethane Mechanophores Enable Full-Visible Spectrum Mechanochromism
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    • James R. Hemmer
      James R. Hemmer
      Adolphe Merkle Institute (AMI), University of Fribourg, Chemin des Verdiers 4, Fribourg 1700, Switzerland
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    • Viola Bauernfeind
      Viola Bauernfeind
      Adolphe Merkle Institute (AMI), University of Fribourg, Chemin des Verdiers 4, Fribourg 1700, Switzerland
      More by Viola Bauernfeind
      Orcidhttps://orcid.org/0000-0001-6612-5883
    • Chris Rader
      Chris Rader
      Adolphe Merkle Institute (AMI), University of Fribourg, Chemin des Verdiers 4, Fribourg 1700, Switzerland
      Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans, 16, Tarragona E-43007, Spain
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      Orcidhttps://orcid.org/0000-0002-5211-7628
    • Manuel Petroselli
      Manuel Petroselli
      Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans, 16, Tarragona E-43007, Spain
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    • Christoph Weder
      Christoph Weder
      Adolphe Merkle Institute (AMI), University of Fribourg, Chemin des Verdiers 4, Fribourg 1700, Switzerland
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      Orcidhttps://orcid.org/0000-0001-7183-1790
    • José Augusto Berrocal*
      José Augusto Berrocal
      Adolphe Merkle Institute (AMI), University of Fribourg, Chemin des Verdiers 4, Fribourg 1700, Switzerland
      Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans, 16, Tarragona E-43007, Spain
      *Email: [email protected]
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      Orcidhttps://orcid.org/0000-0003-3435-8310
    Other Access OptionsSupporting Information (6)

    Macromolecules

    Cite this: Macromolecules 2023, 56, 21, 8614–8622
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    https://doi.org/10.1021/acs.macromol.3c01521
    Published November 1, 2023
    Copyright © 2023 American Chemical Society
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    Abstract

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    Covalent mechanophores are molecular motifs that contain weak bonds, which are preferentially cleaved in response to the application of a mechanical force. Specially designed motifs can signal such bond scission events by changing their optical absorption or emission characteristics and thus exhibit mechanochromism. Here, we report the synthesis of three triarylmethane benzyl ether derivatives and their use as mechanochromic cross-linkers in elastomeric networks. Mechanical stimulation of these polymers triggers the heterolytic cleavage of the C–O ether bond of the triarylmethanes, which leads to the formation of resonance-stabilized carbocations that absorb light in the visible range. The materials adopt blue, yellow, or red coloration depending on the chemical design of the triarylmethane mechanophore. The color palette can be further expanded by simple combinations of these three colors. Thus, our work demonstrates the versatility of the triarylmethane platform in polymer mechanochemistry.

    Copyright © 2023 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.macromol.3c01521.

    • Methods, synthetic procedures, compounds characterization (1H and 13C NMR spectra and FT-IR spectra), thermomechanical characterization of the polymer networks (TGA, DSC, and DMA), spectroscopic and photochemical data, photographs before and after manual pulling, and photographs before and after irradiation with UV light (PDF)

    • Mechanical activation upon manual deformation of P(MA-co-HEA)-Tr-1 (MP4)

    • Mechanical activation upon manual deformation of P(MA-co-HEA)-Tr-2 (MP4)

    • Mechanical activation upon manual deformation of P(MA-co-HEA)-Tr-3 (MP4)

    • Mechanical activation upon manual deformation of P(MA-co-HEA)-(Tr-1+Tr-3) MP4

    • Mechanical activation upon manual deformation of P(MA-co-HEA)-(Tr-2+Tr-3) MP4

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    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

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    This article is cited by 5 publications.

    1. Minghan Hu, Zhongqi Ma, Minsoo Kim, Donghoon Kim, Suiying Ye, Salvador Pané, Yinyin Bao, Robert W. Style, Lucio Isa. Self‐Reporting Multiple Microscopic Stresses Through Tunable Microcapsule Arrays. Advanced Materials 2024, 59 https://doi.org/10.1002/adma.202410945
    2. Niamh Willis-Fox. In-situ monitoring of polymer mechanochemistry: what can be learned from small molecule systems. Frontiers in Chemistry 2024, 12 https://doi.org/10.3389/fchem.2024.1490847
    3. Liang Dong, Luofei Li, Huiyan Chen, Yi Cao, Hai Lei. Mechanochemistry: Fundamental Principles and Applications. Advanced Science 2024, 16 https://doi.org/10.1002/advs.202403949
    4. Xinlei Fu, Longhui Wu, Xiaohua Guo, Kai Yang, Zhaowen Liu. Transition-metal-free synthesis of triarylmethanes via Friedel-Crafts reactions of imidazo[1,2-a]pyridines with chlorohydrocarbon derivatives. Journal of Saudi Chemical Society 2024, 28 (4) , 101883. https://doi.org/10.1016/j.jscs.2024.101883
    5. Kai Yang, Longhui Wu, Xinlei Fu, Weiming Chen, Zhaowen Liu, Xiaopeng Peng. HFIP promoted cyclization of o-hydroxyaryl enaminones with chlorohydrocarbon for synthesis of chromone-containing triarylmethanes. Tetrahedron 2024, 156 , 133948. https://doi.org/10.1016/j.tet.2024.133948
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    Macromolecules

    Cite this: Macromolecules 2023, 56, 21, 8614–8622
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.macromol.3c01521
    Published November 1, 2023
    Copyright © 2023 American Chemical Society
    Request reuse permissions

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