Pentacene to octacene: the limit of fourfold TIPS-ethynylation
<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...
Gespeichert in:
| Hauptverfasser: | , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
01 Februar 2024
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| In: |
Organic materials
Year: 2024, Jahrgang: 6, Heft: 1, Pages: 12-17 |
| ISSN: | 2625-1825 |
| DOI: | 10.1055/a-2241-0243 |
| Online-Zugang: | Verlag, kostenfrei, Volltext: https://doi.org/10.1055/a-2241-0243 Verlag, kostenfrei, Volltext: http://www.thieme-connect.de/DOI/DOI?10.1055/a-2241-0243 
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| Verfasserangaben: | Nico Zeitter, Nikolai Hippchen, Philipp Baur, Tamara V. Unterreiner, Frank Rominger, Jan Freudenberg, Uwe H. F. Bunz |
MARC
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| 245 | 1 | 0 | |a Pentacene to octacene |b the limit of fourfold TIPS-ethynylation |c Nico Zeitter, Nikolai Hippchen, Philipp Baur, Tamara V. Unterreiner, Frank Rominger, Jan Freudenberg, Uwe H. F. Bunz |
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| 520 | |a <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> | ||
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