Facile Covalent Modification of a Highly Ordered Pyrolytic Graphite Surface via an Inverse Electron Demand Diels–Alder Reaction under Ambient Conditions

Chemical derivatization of an sp 2 -hybridized carbon surface under ambient conditions is a challenge. Tetrazine-linked compounds are shown to react with an sp 2 -hybridized 2D carbon surface (highly ordered pyrolytic graphite) under ambient conditions, via an inverse electron demand Diels–Alder reaction. Taking advantage of the facile derivatization of dichlorotetrazine with thiol- or hydroxyl-containing molecules, a variety of tetrazine-terminated functional molecules can be prepared and applied to the preparation of functional carbon materials. The methodology described here is the mildest approach reported to date for the derivatization of an sp 2 -hybridized carbon surface.