Chiral Assemblies from an Achiral Pyridinium-Tailored Anthracene

Jun Hu; Lei Gao; Youliang Zhu; Peiyi Wang; Yuan Lin; Zhaoyan Sun; Song Yang; Qian Wang

doi:10.1002/chem.201604730

Chiral Assemblies from an Achiral Pyridinium-Tailored Anthracene

Chemistry. 2017 Jan 26;23(6):1422-1426. doi: 10.1002/chem.201604730. Epub 2016 Dec 20.

Authors

Jun Hu¹, Lei Gao², Youliang Zhu¹, Peiyi Wang², Yuan Lin¹, Zhaoyan Sun¹, Song Yang², Qian Wang^{1

3}

Affiliations

¹ State Key Lab of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, P. R. China.
² State Key Laboratory of Breeding Base of Green Pesticide and Agricultural Bioengineering, Center for R&D of Fine Chemicals, Guizhou University, Guiyang, 550025, P. R. China.
³ Department of Chemistry and Biochemistry, University of South Carolina, Columbia, SC, 29208, USA.

PMID: 27859755
DOI: 10.1002/chem.201604730

Abstract

Chiral helical structures have attracted increasing attention in the field of supramolecular assembly because of their critical roles in life and material sciences. In this research, the achiral amphiphile 1-[11-(2-anthracenylmethoxy)-11-oxoundecyl]pyridinium bromide (2-APB), in which the hydrophobic anthracene and the hydrophilic pyridinium units are linked by alkyl chains, was found to form chiral supramolecular assemblies in a cooperative manner in the presence of iodide anion. Moreover, these assemblies show left (L)- or right (R)-handedness randomly, independent of the assembly conditions. By using the same method, 2-APB could assemble together with other pseudo-halogen anions (OCN^- , SCN^- , SeCN^- ) that have similar anionic radius as iodide to form chiral structures. This work illustrates a simple and rational design that can be used to fabricate supramolecular chiral structures from achiral molecules.

Keywords: chirality; helical structures; nanostructures; self-assembly; supramolecular chemistry.