3 years ago

Solvent-Directed Helical Stereomutation Discloses Pathway Complexity on N-Heterotriangulene-Based Organogelators

Solvent-Directed Helical Stereomutation Discloses Pathway Complexity on N-Heterotriangulene-Based Organogelators
Luis Sánchez, Francisco J. Ramírez, Juan Casado, Rafael Gómez, Roberto Sánchez-Naya, Jorge S. Valera, José L. Zafra
The chiroptical features of supramolecular polymers formed from N-heterotriangulenes 1–3 have been investigated by circular dichroism (ECD) and vibrational circular dichroism (VCD) techniques. In solution, the CD spectra demonstrate that the helicity of the aggregates depends on only the stereogenic centres located at the peripheral chains. In the gel state, the chiroptical features are conditioned by the point chirality of the stereogenic centres and by the achiral solvent utilised. Sonication of the gels formed in CCl4 reveals both kinetic and thermodynamic phases. These findings reveal the presence of pathway complexity in the gel state triggered by sonication. The described solvent-induced helical stereomutation demonstrates that the gel state can be utilised as an outstanding benchmark for investigating uncommon chiroptical effects and to explore the rules of chirality transmission. Twists and turns: The chiroptical features of supramolecular polymers formed from N-heterotriangulenes 1–3 have been investigated by circular dichroism and vibrational circular dichroism techniques. Solvent-directed pathway complexity, yielding kinetic or thermodynamic aggregates, is observed for N-heterotriangulenes 1–3 in the gel state (see figure).

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201702391

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