Carbamate-Protected (BOC and O‑NB) 2‑Aminopyrimidinedione-Based Janus G‑C Nucleobase Motifs as Building Blocks for Supramolecular Assembly and Smart Polymers

In this paper, we report “carbamate protected” 2-aminopyrimidinedione-based Janus G-C nucleobases (2-APD Janus G-C nucleobases) featuring polymerizable groups and self-complementary triple H-bonding motifs DDA and AAD as building blocks for developing smart polymers and self-healing materials. The c...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-11, Vol.88 (21), p.14953-14959
Main Authors: Singh, Dharmendra, Lakshmi, Durga, Meena, Chhuttan L., Krishna, Gamidi Rama, Sanjayan, Gangadhar J.
Format: Article
Language:English
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Summary:In this paper, we report “carbamate protected” 2-aminopyrimidinedione-based Janus G-C nucleobases (2-APD Janus G-C nucleobases) featuring polymerizable groups and self-complementary triple H-bonding motifs DDA and AAD as building blocks for developing smart polymers and self-healing materials. The carbamate-masked H-bonding motif, cleavable under acidic (BOC group) or photocleavable (O-nitrobenzyl group) conditions, would facilitate the synthesis of smart polymers by alleviating aggregation during polymerization which in turn would exclude self-assembly-assisted solubility issues. Ready accessibility in excellent yields coupled with the possibility for facile introduction of polymerizable groups would make these building blocks excellent candidates for diverse polymerization applications.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c01318