4.8 Article

Solvent-Dependent Disassembly of Amphiphilic OPE-Based Tricarboxamides

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ORGANIC LETTERS
卷 15, 期 22, 页码 5746-5749

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AMER CHEMICAL SOC
DOI: 10.1021/ol402788n

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  1. MINECO of Spain [CTQ2011-22581]
  2. MINECO

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A series of water-compatible C-3-symmetric tricarboxamides endowed with a large number of EO side chains separated from the amide groups by different paraffinic linkers has been synthesized. The addition of a small amount of water breaks the N-H center dot center dot center dot O=C amide H-bonds but induces the formation of aggregates by a solvophobic effect. The lack of highly directional H-bonding interactions results in an isodesmic supramolecular polymerization with a calculated Gibbs free energy of -31.26 and -36.79 kJ mol(-1) for 1 and 3, respectively.

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