Synthesis of a Tetracorannulene-perylenediimide That Acts as a Selective Receptor for C60 over C70

Org Lett. 2019 Aug 2;21(15):5803-5807. doi: 10.1021/acs.orglett.9b01729. Epub 2019 Jun 26.

Abstract

We report the use of a tetraborylated perylenediimide as starting material for the preparation of a tetracorannulene-perylenediimide that is able to bind up to two fullerene-C60 molecules by host-guest molecular recognition with preference over C70. Titration with fullerene-C60 is followed by a dramatic shift of the aromatic signals in 1H NMR and an initial increase in the fluorescence of the system. By this simple mechanism, fluorogenic sensing of fullerene-C60 is easily accomplished by an unprecedented fluorescent turn-on mechanism.

Publication types

  • Research Support, Non-U.S. Gov't