Open AccessFrom Sequence‐Defined Macromolecules to Macromolecular Pin Codes
Author(s) -
Holloway Joshua O.,
Van Lijsebetten Filip,
Badi Nezha,
Houck Hannes A.,
Du Prez Filip E.
Publication year - 2020
Publication title -
advanced science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.388
H-Index - 100
ISSN - 2198-3844
DOI - 10.1002/advs.201903698
Subject(s) - scrambling , macromolecule , electrospray ionization , encryption , sequence (biology) , covalent bond , mass spectrometry , chemistry , polymer , combinatorial chemistry , code (set theory) , decipher , computer science , materials science , nanotechnology , biological system , bioinformatics , algorithm , chromatography , organic chemistry , biochemistry , biology , set (abstract data type) , programming language , operating system
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.