Fulvalene‐Based Polycyclic Aromatic Hydrocarbon Ladder‐Type Structures: Synthesis and Properties
| Autor: | Mogens Nielsen, Anders Kadziola, Andreas Erbs Hillers-Bendtsen, Kurt V. Mikkelsen, Viktor Bliksted Roug Pedersen, Jeppe Granhøj |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
Fulvalene 010405 organic chemistry Chemistry Graphene Organic Chemistry Thio Polycyclic aromatic hydrocarbon General Chemistry 010402 general chemistry Electrochemistry 01 natural sciences Catalysis 0104 chemical sciences law.invention chemistry.chemical_compound Computational chemistry law Reagent Absorption (chemistry) Tetrathiafulvalene |
| Zdroj: | Chemistry – A European Journal. 27:8315-8324 |
| ISSN: | 1521-3765 0947-6539 |
| Popis: | Polycyclic aromatic hydrocarbons (PAHs) have found strong interest for their electronic properties and as model systems for graphene. While PAHs have been studied intensively as single units, here PAHs were constructed in ladder-type arrangements using cross-conjugated fulvalene and dithiafulvalene motifs as connecting units and moving forward a convenient synthetic approach for dimerizing (thio)ketones into olefins by the action of Lawesson's reagent. Some of the PAHs can also be regarded as "super-extended" tetrathiafulvalenes (TTFs) with some of the largest cores ever explored, being multi-redox systems that exhibit both reversible oxidations and reductions. Concomitant absorption redshifts were observed when expanding the ladder-type structures from one to two to three indenofluorene units, and optical and electrochemical HOMO-LUMO gaps were found to correlate linearly. Various conformations (and solid-state packing arrangements) were studied by X-ray crystallography and computations. |
| Databáze: | OpenAIRE |
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