Observing the intricate chemical transformation of an individual molecule as it undergoes a complex reaction is a longstanding challenge in molecular imaging. Advances in scanned probe microscopy now provide the tools to visualize not only the frontier orbitals of chemical reaction partners and products, but their internal covalent bond configurations as well. Here we demonstrate the use of noncontact atomic force microscopy to investigate reaction-induced changes in the detailed internal bond structure of individual oligo-(phenylene-1,2-ethynylenes) on Ag(100) as they undergo a series of cyclization processes. Our images reveal the complex surface reaction mechanisms underlying thermally induced cyclization cascades of enediynes. Additional evidence for the proposed reaction pathways is obtained using ab initio density functional theory.

Atomic resolution imaging of the covalent assembly of organic nanomaterials on surfaces

246th National Meeting (2013)

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