Abstract
Exchanging 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.
| Original language | English |
|---|---|
| Article number | e202304361 |
| Pages (from-to) | 1-6 |
| Number of pages | 6 |
| Journal | Chemistry - A European Journal |
| Volume | 30 |
| Issue number | 24 |
| Early online date | 29 Jan 2024 |
| DOIs | |
| Publication status | Published - 25 Apr 2024 |
Bibliographical note
Publisher Copyright:© 2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Funding
The authors thank the Dutch Research Council (NWO) for financial support. The ball-and-stick structures in this article were created using the CYLview20[19] visualization software.
| Funders | Funder number |
|---|---|
| Nederlandse Organisatie voor Wetenschappelijk Onderzoek |
Keywords
- Carbonyl chemistry
- Chalcogens
- Organocatalysis
- Photochemistry
- Supramolecular chemistry