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...
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| Main Authors: | , , , , , , |
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| Format: | Database Research Data |
| Language: | English |
| Published: |
Heidelberg
Universität
2024-01-22
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| DOI: | 10.11588/data/DDJFGS |
| Subjects: | |
| Online Access: | 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 
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| Author Notes: | Nico Zeitter, Nikolai Hippchen, Philipp Baur, Tamara Unterreiner, Jan Freudenberg, Frank Rominger, Uwe Bunz |
| Summary: | 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. |
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| Item Description: | Finanziert durch: DFG: SFB 1249 Gesehen am 14.03.2024 |
| Physical Description: | Online Resource |
| DOI: | 10.11588/data/DDJFGS |