Affiliation:
1. Department of Chemistry and Pharmaceutical Sciences Amsterdam Institute of Molecular and Life Sciences (AIMMS), Vrije Universiteit Amsterdam De Boelelaan 1108 1081 HZ Amsterdam, The Netherlands
Abstract
AbstractExchanging oxygen in the functional group C=O (i. e., carbonyl) for the less electronegative Group 16 elements, sulfur or selenium, unexpectedly enhances the electronegativity of the C=X group in π‐conjugated molecules and reduces the molecular π HOMO–LUMO energy gap. Quantum‐chemical analyses revealed that the steric size of the chalcogen atom X is at the origin of this seemingly counterintuitive behavior. This tuning of the chemical properties of carbonyl compounds by varying the chalcogen atom size in the C=X bond can be applied in many fields of chemistry. This concept article delineates several useful applications in the fields of organocatalysis, supramolecular chemistry, and photo(electro)chemistry.
Funder
Nederlandse Organisatie voor Wetenschappelijk Onderzoek