Pyrrole PMOs, incorporating new N-heterocyclic compounds on an ethene-PMO through Diels–Alder reactions

•Chemical modification of the double bonds on an ethene-PMO through the Diels–Alder reaction.•A family of pyrrole derivatives act as dienes in the Diels–Alder reaction.•Well-ordering and mesoporosity are retained after the post-functionalization.•N-containing compounds on the surface of ethene-PMO are present after the Diels–Alder reaction.

The ethenylene bridges on the walls of an ethenylene-bridged periodic mesoporous organosilica were successfully modified with a variety of pyrrole derivatives – pyrrole, methylpyrrole, dimethylpyrrole, trimethylpyrrole and 1-phenylpyrrole – through Diels–Alder reactions. X-ray diffraction measurements and N2 adsorption–desorption analysis confirmed the preservation of the ordering and mesoporosity of the parent material as well as the decoration of the pores with the surface Diels–Alder adducts. Moreover, other techniques such as DRIFT, 13C and 29Si nuclear magnetic resonances revealed the formation of the surface N-heterocyclic compounds at the parent ethenylene sites.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide