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: Rominger, Frank [VerfasserIn]
• Verfasst von: Freudenberg, Jan [VerfasserIn]
• Verfasst von: Bunz, Uwe H. F. [VerfasserIn]
• Titel: Pentacene to octacene
• Titelzusatz: the limit of fourfold TIPS-ethynylation
• Verf.angabe: Nico Zeitter, Nikolai Hippchen, Philipp Baur, Tamara V. Unterreiner, Frank Rominger, Jan Freudenberg, Uwe H. F. Bunz
• E-Jahr: 2024
• Jahr: 01 Februar 2024
• Umfang: 6 S.
• Illustrationen: Illustrationen
• Fussnoten: Gesehen am 14.03.2024
• Titel Quelle: Enthalten in: Organic materials
• Ort Quelle: Stuttgart : Georg Thieme Verlag KG, 2019
• Jahr Quelle: 2024
• Band/Heft Quelle: 6(2024), 1, Seite 12-17
• ISSN Quelle: 2625-1825
• DOI: doi:10.1055/a-2241-0243
• Datenträger: Online-Ressource
• Sprache: eng
• Bibliogr. Hinweis: Forschungsdaten: Zeitter, Nico, 1993 - : Pentacene to octacene
• K10plus-PPN: 1883465931

Abstract

<p>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 tri-<i>iso</i>-propylsilylethynyl-ethynylated pentacenes to octacenes and investigate their optical and redox properties, frontier orbital positions (CV, density functional theory 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.</p>