Amphiphilic Organic Cages: Self-Assembly into Nanotubes and Enhanced Anion-π Interactions

Zi-Ying Li; Chuanlong Li; Pan Li; Yong Zuo; Xiaoning Liu; Shijun Xu; Lingyi Zou; Qixin Zhuang; Shan Gao; Xiaoyun Liu; Shaodong Zhang

doi:10.1002/cplu.202000143

Amphiphilic Organic Cages: Self-Assembly into Nanotubes and Enhanced Anion-π Interactions

Chempluschem. 2020 May;85(5):906-909. doi: 10.1002/cplu.202000143.

Authors

Zi-Ying Li¹, Chuanlong Li², Pan Li², Yong Zuo², Xiaoning Liu², Shijun Xu¹, Lingyi Zou², Qixin Zhuang¹, Shan Gao³, Xiaoyun Liu¹, Shaodong Zhang²

Affiliations

¹ Key Laboratory of Specially Functional Polymeric Materials and Related Technology (ECUST) Ministry of Education, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, P. R. China.
² Frontiers Science Centre for Transformative Molecules Shanghai Key Laboratory of Electrical Insulation and Thermal Aging School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, P. R. China.
³ Neurological Department, Shanghai Jiao Tong University Affiliated Sixth People Hospital South Campus, Shanghai, 200240, P. R. China.

PMID: 32401409
DOI: 10.1002/cplu.202000143

Abstract

An amphiphilic organic cage was synthesized and used as self-assembly synthon for the fabrication of novel functional supramolecular structures in solution. The transmission electron microscopy (TEM) results showed that this amphiphilic cage self-assembled in aqueous solution into unilamellar nanotubes with a diameter of 29±4 nm at a concentration of 0.05 mg mL^-1 . Interestingly, the self-assembly of this cage significantly enhanced the anion-π interactions as indicated by a remarkable increasement of association constant (K_a ) between Cl^- and this amphiphilic cage after self-assembly. In specific, K_a was increased from 223 M^-1 for discrete cages in methanol to 6800 M^-1 for aggregated cages after self-assembly in water at the same concentration of 2.26×10^-5 M. A mechanism based on a synergistic effect was proposed in order to explain this self-assembly process through enhanced anion-π interactions.

Keywords: amphiphiles; anion-π interactions; nanotubes; organic cages; self-assembly.

Publication types

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