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From sequence-defined macromolecules to macromolecular pin codes

Joshua Holloway (UGent) , Filip Van Lysebetten (UGent) , Nezha Badi (UGent) , Hannes Houck (UGent) and Filip Du Prez (UGent)
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Organization
Abstract
Dynamic sequence-defined oligomers carrying a chemically written pin code are obtained through a strategy combining multicomponent reactions with the thermoreversible addition of 1,2,4-triazoline-3,5-diones (TADs) to indole substrates. The precision oligomers are specifically designed to be encrypted upon heating as a result of the random reshuffling of the TAD-indole covalent bonds within the backbone, thereby resulting in the scrambling of the encoded information. The encrypted pin code can eventually be decrypted following a second heating step that enables the macromolecular pin code to be deciphered using 1D electrospray ionization-mass spectrometry (ESI-MS). The herein introduced concept of encryption/decryption represents a key advancement compared with current strategies that typically use uncontrolled degradation to erase and tandem mass spectrometry (MS/MS) to analyze, decipher, and read-out chemically encrypted information. Additionally, the synthesized macromolecules are coated onto a high-value polymer material, which demonstrates their potential application as coded product tags for anti-counterfeiting purposes.
Keywords
NEXT-GENERATION, STORAGE, INFORMATION, DESIGN, CLICK, 1, 2, 4-triazoline-3, 5-dione, chemical encryption, multicomponent, reactions, sequence-defined macromolecules

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Citation

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MLA
Holloway, Joshua, et al. “From Sequence-Defined Macromolecules to Macromolecular Pin Codes.” ADVANCED SCIENCE, vol. 7, no. 8, 2020, doi:10.1002/advs.201903698.
APA
Holloway, J., Van Lysebetten, F., Badi, N., Houck, H., & Du Prez, F. (2020). From sequence-defined macromolecules to macromolecular pin codes. ADVANCED SCIENCE, 7(8). https://doi.org/10.1002/advs.201903698
Chicago author-date
Holloway, Joshua, Filip Van Lysebetten, Nezha Badi, Hannes Houck, and Filip Du Prez. 2020. “From Sequence-Defined Macromolecules to Macromolecular Pin Codes.” ADVANCED SCIENCE 7 (8). https://doi.org/10.1002/advs.201903698.
Chicago author-date (all authors)
Holloway, Joshua, Filip Van Lysebetten, Nezha Badi, Hannes Houck, and Filip Du Prez. 2020. “From Sequence-Defined Macromolecules to Macromolecular Pin Codes.” ADVANCED SCIENCE 7 (8). doi:10.1002/advs.201903698.
Vancouver
1.
Holloway J, Van Lysebetten F, Badi N, Houck H, Du Prez F. From sequence-defined macromolecules to macromolecular pin codes. ADVANCED SCIENCE. 2020;7(8).
IEEE
[1]
J. Holloway, F. Van Lysebetten, N. Badi, H. Houck, and F. Du Prez, “From sequence-defined macromolecules to macromolecular pin codes,” ADVANCED SCIENCE, vol. 7, no. 8, 2020.
@article{8658537,
  abstract     = {Dynamic sequence-defined oligomers carrying a chemically written pin code are obtained through a strategy combining multicomponent reactions with the thermoreversible addition of 1,2,4-triazoline-3,5-diones (TADs) to indole substrates. The precision oligomers are specifically designed to be encrypted upon heating as a result of the random reshuffling of the TAD-indole covalent bonds within the backbone, thereby resulting in the scrambling of the encoded information. The encrypted pin code can eventually be decrypted following a second heating step that enables the macromolecular pin code to be deciphered using 1D electrospray ionization-mass spectrometry (ESI-MS). The herein introduced concept of encryption/decryption represents a key advancement compared with current strategies that typically use uncontrolled degradation to erase and tandem mass spectrometry (MS/MS) to analyze, decipher, and read-out chemically encrypted information. Additionally, the synthesized macromolecules are coated onto a high-value polymer material, which demonstrates their potential application as coded product tags for anti-counterfeiting purposes.},
  articleno    = {1903698},
  author       = {Holloway, Joshua and Van Lysebetten, Filip and Badi, Nezha and Houck, Hannes and Du Prez, Filip},
  issn         = {2198-3844},
  journal      = {ADVANCED SCIENCE},
  keywords     = {NEXT-GENERATION,STORAGE,INFORMATION,DESIGN,CLICK,1,2,4-triazoline-3,5-dione,chemical encryption,multicomponent,reactions,sequence-defined macromolecules},
  language     = {eng},
  number       = {8},
  pages        = {7},
  title        = {From sequence-defined macromolecules to macromolecular pin codes},
  url          = {http://dx.doi.org/10.1002/advs.201903698},
  volume       = {7},
  year         = {2020},
}

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