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• W2047669007 abstract "We report the synthesis and characterization of 12 C-shaped methylene-bridged glycoluril dimers (1−12) 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 1−12 as robust, functionalizable, self-sorting modules to control the noncovalent interaction network in systems chemistry studies is described." @default.
• W2047669007 created "2016-06-24" @default.
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• W2047669007 date "2008-06-28" @default.
• W2047669007 modified "2023-10-15" @default.
• W2047669007 title "Self-Sorting Molecular Clips" @default.
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• W2047669007 doi "https://doi.org/10.1021/jo8009424" @default.
• W2047669007 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/18588344" @default.
• W2047669007 hasPublicationYear "2008" @default.
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