Organosulfonates aid argentophilic forces in the crystal engineering of [2+2] photodimerisations: reactivity involving 3-pyridyl groups

Abstract

Photoreactive Ag(I) organosulfonate complexes involving (E)-methyl-3-(pyridin-3-yl)prop-2-enoate (3-PAMe) are reported. Argentophilic interactions stack 3-PAMe to undergo a head-to-head intermolecular [2+2] photodimerisation to generate (rctt)-dimethyl-3,4-bis(pyridine-3-yl)cyclobutane-1,2-dicarboxylate (3,3′-MeBPCD) in the solid state regioselectively and in quantitative yield. The organosulfonate participates in C–H…O interactions with the coordinated 3-pyridyl groups to effectively aid in crystal engineering of the reactivity.

Keywords::

• supramolecular chemistry
• [2+2] photodimerisation
• crystal engineering

Additional information

Funding

We are grateful to the National Science Foundation (L.R.M., DMR-1104650) for funding.