Issue 43, 2014

Aggregation-induced chiral symmetry breaking of a naphthalimide–cyanostilbene dyad

Abstract

Spontaneously emerged supramolecular chirality and chiral symmetry breaking from achiral/racemic constituents remain poorly understood. We here report that supramolecular chirality may emerge from the structural flexibility of achiral aryl nitrogen centres which provide instantaneous chirality. Employing a naphthalimide–cyanostilbene dyad as a model, we explored the underlying mechanism of aggregation-induced chiral symmetry breaking and found that the conformations of the N-naphthylpiperazine and the N,N-dimethylaniline units facilitate the formation of ordered supramolecular structures and offer opposite handedness. Furthermore, chiral symmetry breaking of the monomers was amplified by the formation of dimers. The microscopic and the macroscopic observations from the theoretical simulations and experimental measurements are thus rationalized by connecting the population of the dihedral angles of the aryl nitrogen centres, the morphology of the self-assemblies, and the observed circular dichroism spectra.

Graphical abstract: Aggregation-induced chiral symmetry breaking of a naphthalimide–cyanostilbene dyad

Supplementary files

Article information

Article type
Paper
Submitted
10 Sep 2014
Accepted
25 Sep 2014
First published
26 Sep 2014

Phys. Chem. Chem. Phys., 2014,16, 23854-23860

Aggregation-induced chiral symmetry breaking of a naphthalimide–cyanostilbene dyad

X. Li, L. Zhu, S. Duan, Y. Zhao and H. Ågren, Phys. Chem. Chem. Phys., 2014, 16, 23854 DOI: 10.1039/C4CP04070H

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