Dimerization control in the self-assembly behavior of copillar[5]arenes bearing ω-hydroxyalkoxy groups

Luzhi Liu; Lingyun Wang; Changchun Liu; Zhiyong Fu; Herbert Meier; Derong Cao

doi:10.1021/jo301779y

Dimerization control in the self-assembly behavior of copillar[5]arenes bearing ω-hydroxyalkoxy groups

J Org Chem. 2012 Oct 19;77(20):9413-7. doi: 10.1021/jo301779y. Epub 2012 Oct 4.

Authors

Luzhi Liu¹, Lingyun Wang, Changchun Liu, Zhiyong Fu, Herbert Meier, Derong Cao

Affiliation

¹ School of Chemistry and Chemical Engineering, State Key Lab of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510641, China.

PMID: 22998632
DOI: 10.1021/jo301779y

Abstract

Two novel copillar[5]arenes bearing ω-hydroxyalkoxy groups are synthesized and their self-assembly properties are studied by (1)H NMR spectroscopy, specific viscosity, and X-ray measurements. The copillar[5]arene 2b bearing a 6-hydroxyhexyloxy group exhibits a reversible self-assembly behavior, leading to the formation of the self-inclusion monomer and hugging dimers. The reversible self-assembly behavior can be controlled by tuning solvent, temperature, guest, and H-bond interaction. However, the copillar[5]arene 2a bearing a short 4-hydroxybutyloxy group does not show such a self-assembly behavior to the formation of the self-inclusion monomer and hugging dimers.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alcohols / chemistry*
Benzene Derivatives / chemical synthesis*
Benzene Derivatives / chemistry
Bridged-Ring Compounds / chemical synthesis*
Bridged-Ring Compounds / chemistry
Dimerization
Models, Molecular
Molecular Structure

Substances

Alcohols
Benzene Derivatives
Bridged-Ring Compounds
alkoxyl radical