Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 12, Pages 2826-2831Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201706070
Keywords
amplification of chirality; helicity; self-sorting; supramolecular polymers; theoretical calculations
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Funding
- MINECO of Spain [CTQ2014-53046-P, CTQ2015-71154-P]
- MINECO of Spain (Unidad de Excelencia Maria de Maeztu) [MDM-2015-0538]
- Generalitat Valenciana [PROMETEO/2016/ 135, APOSTD/2017/081]
- Comunidad de Madrid (NanoBIOSOMA) [S2013/MIT-2807]
- European FEDER funds [CTQ2015-71154-P]
- MINECO
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A detailed investigation of the hierarchy of asymmetry operating in the self-assembly of achiral (1) and chiral ((S)-2 and (R)-3) 1,3,5-triphenylbenzenetricar-boxamides (TPBAs) is reported. The aggregation of these TPBAs is conditioned by the point chirality at the peripheral side chains for (S)-2 and (R)-3. An efficient helix-tohelix interaction that goes further in the organization of fibrillar bundles is experimentally detected and theoretically supported only for the achiral TPBA 1. The effective interdigitation of the achiral aliphatic side chains produces a social self-sorting to form preferentially heterochiral macromolecular aggregates.
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