%0 Generic %A Ghosh, Soumyadip %A Wu, Anxin %A Fettinger, James C. %A Zavalij, Peter Y. %A Isaacs, Lyle %D 2008 %T Self-Sorting Molecular Clips %U https://acs.figshare.com/articles/dataset/Self_Sorting_Molecular_Clips/2924272 %R 10.1021/jo8009424.s002 %2 https://acs.figshare.com/ndownloader/files/5339497 %K mixture %K noncovalent interaction network %K Compound %K side chain steric bulk %K systems chemistry studies %K e.g %K homodimer %K clip %K CDCl 3 %X We report the synthesis and characterization of 12 C-shaped methylene-bridged glycoluril dimers (112) bearing H-bonding groups on their aromatic rings. Compounds 1, 2, (±)-4a, (±)-5, (±)-7, and 8 form tightly associated homodimers in CDCl3, due to the combined driving force of π−π and H-bonding interactions. Compounds 2, (±)-5, and 8, having disparate spatial distribution of their H-bonding groups, display the ability to efficiently distinguish between self and nonself even within three-component mixtures in CDCl3. When the spatial distributions of the H-bonding groups of the molecular clips are similar (e.g., 1 and 2), a mixture of homodimers and heterodimers is formed. The effect of various structural modifications (e.g., chirality, side chain steric bulk, number and pattern of H-bonds) on the strength of self-assembly and the fidelity of self-sorting are presented. On the basis of these results we prepared self-sorting systems comprising three (e.g., 1, (±)-5, and (±)-7) and even four (2, (±)-5, 9, and 10) components. The potential of molecular clips 112 as robust, functionalizable, self-sorting modules to control the noncovalent interaction network in systems chemistry studies is described. %I ACS Publications