Pentacene to octacene

• Verfasst von: Zeitter, Nico [VerfasserIn]
• Verfasst von: Hippchen, Nikolai [VerfasserIn]
• Verfasst von: Baur, Philipp [VerfasserIn]
• Verfasst von: Unterreiner, Tamara [VerfasserIn]
• Verfasst von: Freudenberg, Jan [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Bunz, Uwe H. F. [VerfasserIn]
• Titel: Pentacene to octacene
• Titelzusatz: the limit of fourfold TIPS-ethynylation [data]
• Verf.angabe: Nico Zeitter, Nikolai Hippchen, Philipp Baur, Tamara Unterreiner, Jan Freudenberg, Frank Rominger, Uwe Bunz
• Verlagsort: Heidelberg
• Verlag: Universität
• E-Jahr: 2024
• Jahr: 2024-01-22
• Umfang: 1 Online-Ressource (4 Files)
• Fussnoten: Finanziert durch: DFG: SFB 1249 ; Gesehen am 14.03.2024
• DOI: doi:10.11588/data/DDJFGS
• Datenträger: Online-Ressource
• Dokumenttyp: Forschungsdaten
• Dokumenttyp: Datenbank
• Sprache: eng
• Bibliogr. Hinweis: Forschungsdaten zu: Zeitter, Nico: Pentacene to octacene
• Sonstige Nr.: Grant number: DFG: SFB 1249
• Sach-SW: Chemistry
• K10plus-PPN: 1883465230
• K10plus-PPN:
  Universitätsbibliothek
• Lokale URL UB: Zum Volltext

Abstract

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.