Synthesis of a Tetracorannulene-perylenediimide That Acts as a Selective Receptor for C over C.

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-C molecules by host-guest molecular recognition with preference over C. Titration with fullerene-C is followed by a dramatic shift of the aromatic signals in H NMR and an initial increase in the fluorescence of the system. By this simple mechanism, fluorogenic sensing of fullerene-C is easily accomplished by an unprecedented fluorescent turn-on mechanism.