Cyclotriveratrylene (CTV)

The bowl-shaped supramolecular scaffold cyclotriveratrylene (CTV) has been studied extensively1 because of its ability to function as a host in host-guest chemistry for C60 as well as a number of small molecules, and its use in construction of cryptands. Our research has focused on apex-modified CTV derivatives and reactivity and their molecular dynamics. The azacyclophane “N3-CTV” is an apex-modified analog of CTV including three amine (aniline) moieties comprising the 9-membered ring.  While exploring metal complexation, we discovered a copper bromide-mediated oxidative rearrangement to a stable cation radical, and separately we demonstrate peripheral functionalization of the azacyclophane.


N3-CTV

The azacyclophane “N3-CTV” is an apex-modified analog of CTV including three amine (aniline) moieties comprising the 9-membered ring.  While exploring metal complexation, we discovered a copper bromide-mediated oxidative rearrangement to a stable cation radical, and separately we demonstrate peripheral functionalization of the azacyclophane.



Synthesis of N3-CTV

The synthesis of N3-CTV proceeds via sequential Buchwald-Hartwig coupling reactions.