RT Journal Article
T1 Impact of molecular size and shape on the supramolecular co-assembly of chiral ticarboxamides: a comparative study
A1 Dorca, Yeray
A1 Sánchez-Naya, Roberto
A1 Cerdá, Jesús
A1 Calbo, Joaquín
A1 Aragó, Juan
A1 Gómez Aspe, Rafael
A1 Ortí, Enrique
A1 Sánchez Martín, Luis
AB A comparative investigation of the chiral amplification features of a series of three families of C3-symmetric tricarboxamides, 1,3,5-triphenylbenzenetricarboxamides (TPBAs), benzenetricarboxamides (BTAs) and oligo(phenylene ethynylene) tricarboxamides (OPE-TAs), is here reported. As previously observed for BTAs and OPE-TAs, a similar dichroic response is obtained for TPBAs decorated with one, two or three chiral side chains bearing stereogenic centers, thus confirming the efficient transfer of point chirality to the supramolecular helical aggregates. Unlike BTAs and OPE-TAs, the chiral amplification ability of TPBAs in majority rules experiments shows a negligible dependence on the number of chiral centers per monomeric unit, and stands the largest among the series of tricarboxamides. Detailed experimental and theoretical studies demonstrate that the rotation angle between the TPBA units in the helical stack is intermediate to that observed for BTAs and OPE-TAs. This feature strongly conditions the steric interactions between vicinal molecules in the stack and the final chiral amplification outcome. Furthermore, theoretical calculations show that achiral side chains favor the interdigitation of the helical aggregates and thereby the formation of bundle superstructures.
PB Wiley-VCH
YR 2020
FD 2020
LK https://hdl.handle.net/20.500.14352/105846
UL https://hdl.handle.net/20.500.14352/105846
LA eng
NO MCIU of Spain
DS Docta Complutense
RD 10 abr 2025