Cation-Assisted Reversible Folding and Anion Binding by a Naphthalenediimide-Based Ditopic Ion-Pair Receptor

Krishnendu Maity; Dillip K Panda; Robert J Gallup; Chandan K Choudhury; Sourav Saha

doi:10.1021/acs.orglett.7b03861

Cation-Assisted Reversible Folding and Anion Binding by a Naphthalenediimide-Based Ditopic Ion-Pair Receptor

Org Lett. 2018 Feb 16;20(4):962-965. doi: 10.1021/acs.orglett.7b03861. Epub 2018 Feb 6.

Authors

Krishnendu Maity¹, Dillip K Panda¹, Robert J Gallup¹, Chandan K Choudhury², Sourav Saha¹

Affiliations

¹ Department of Chemistry, Clemson University , Clemson, South Carolina 29634, United States.
² Department of Materials Science and Engineering, Clemson University , Clemson, South Carolina 29634, United States.

PMID: 29406725
DOI: 10.1021/acs.orglett.7b03861

Abstract

A novel heteroditopic ion-pair receptor was synthesized by tethering two π-acidic naphthalenediimide units with a tridentate bisimine linker. Upon chelating a Zn^II or Cd^II ion with the linker, it adopts a U-conformation allowing the parallel NDI arms to sandwich charge-diffuse anions, and two such folded receptor molecules interlock with each other forming an [R3·M^II·R3·X^-] ion-pair complex. Extraction of the guest cation with a tetraazacrown ether returns the receptor to its original unfolded form.

Publication types

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