From Sequence-Defined Macromolecules to Macromolecular Pin Codes.
1,2,4‐triazoline‐3,5‐dione
chemical encryption
multicomponent reactions
sequence‐defined macromolecules
Journal
Advanced science (Weinheim, Baden-Wurttemberg, Germany)
ISSN: 2198-3844
Titre abrégé: Adv Sci (Weinh)
Pays: Germany
ID NLM: 101664569
Informations de publication
Date de publication:
Apr 2020
Apr 2020
Historique:
received:
19
12
2019
revised:
10
02
2020
entrez:
25
4
2020
pubmed:
25
4
2020
medline:
25
4
2020
Statut:
epublish
Résumé
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.
Identifiants
pubmed: 32328435
doi: 10.1002/advs.201903698
pii: ADVS1632
pmc: PMC7175230
doi:
Types de publication
Journal Article
Langues
eng
Pagination
1903698Informations de copyright
© 2020 The Authors. Published by WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim.
Déclaration de conflit d'intérêts
The authors declare no conflict of interest.
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