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.