The stereocontrol of chemical reactions on surfaces is one of the most challenging tasks in developing new generations of highly selective heterogeneous asymmetric catalysts. STM imaging coupled with DFT calculations provides a uniquely powerful method for addressing the current lack of a detailed molecular understanding of catalytic asymmetric induction on surfaces. In combination, these techniques can be used to observe and define transient chemisorbed pre-organization complexes operating the chirality transfer. We present sub-molecularly resolved regiospecific and stereospecific data for isolated bimolecular and termolecular assemblies formed between chiral and prochiral molecules on a platinum surface. The studies were performed using a combination of variable temperature STM imaging, DFT calculations, catalytic tests, and organic chemistry approaches. The results show how site-specific chemisorption can cooperate with multiple non-covalent bonding in the formation of stereodirecting complexes. They also show how surface analysis at the molecular scale can be bridged to organic chemistry problems.

Designing and imaging isolated bimolecular stereospecific structures on a platinum surface

245th National Meeting (2013)

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