Pentacene to octacene: the limit of fourfold TIPS-ethynylation [data]
Soluble acenes beyond hexacene are rare. Their sensitivity complicates isolation, purification and application in devices. To increase the stability of acenes, functionalization with trialkylsilylethynyl substituents prevents [4+4] dimerization and oxidation. At the same time such acenes are soluble...
Gespeichert in:
| Hauptverfasser: | , , , , , , |
|---|---|
| Dokumenttyp: | Datenbank Forschungsdaten |
| Sprache: | Englisch |
| Veröffentlicht: |
Heidelberg
Universität
2024-01-22
|
| DOI: | 10.11588/data/DDJFGS |
| Schlagworte: | |
| Online-Zugang: | Verlag, kostenfrei, Volltext: https://doi.org/10.11588/data/DDJFGS Verlag, kostenfrei, Volltext: https://heidata.uni-heidelberg.de/dataset.xhtml?persistentId=doi:10.11588/data/DDJFGS 
|
| Verfasserangaben: | Nico Zeitter, Nikolai Hippchen, Philipp Baur, Tamara Unterreiner, Jan Freudenberg, Frank Rominger, Uwe Bunz |
| Zusammenfassung: | Soluble acenes beyond hexacene are rare. Their sensitivity complicates isolation, purification and application in devices. To increase the stability of acenes, functionalization with trialkylsilylethynyl substituents prevents [4+4] dimerization and oxidation. At the same time such acenes are soluble and processible. Here we present the modular synthesis of fourfold TIPS-ethynylated pentacenes to octacenes and investigate their optical and redox properties, frontier orbital positions (CV, DFT calculations) as well as their stability in solution (UV/vis, NMR spectroscopy). We also investigated their magnetic properties as a function of acene length. Pentacene, hexacene and heptacene are sufficiently stable to serve as semiconductors in thin-film transistors - the octacene rapidly decays to its butterfly dimer evidence by time-dependent NMR spectroscopy and crystal structure analysis. |
|---|---|
| Beschreibung: | Finanziert durch: DFG: SFB 1249 Gesehen am 14.03.2024 |
| Beschreibung: | Online Resource |
| DOI: | 10.11588/data/DDJFGS |