Molecular Tetris by sequence-specific stacking of hydrogen bonding molecular clips.

ABSTRACT: A face-to-face stacking of aromatic rings is an effective non-covalent strategy to build functional architectures, as elegantly exemplified with protein folding and polynucleotide assembly. However, weak, non-directional, and context-sensitive van der Waals forces pose a significant challenge if one wishes to construct well-organized π-stacks outside the confines of the biological matrix. To meet this design challenge, we have devised a rigid polycyclic template to create a non-collapsible void between two parallel oriented π-faces. In solution, these shape-persistent aromatic clips self-dimerize to form quadruple π-stacks, the thermodynamic stability of which is enhanced by self-complementary N-H···N hydrogen bonds, and finely regulated by the regioisomerism of the π-canopy unit. With ass

SUBMITTER: Lee H 

PROVIDER: S-EPMC9814962 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature