Stabilizing azaheptacenes
The symmetrical 7,16-diaza-6,8,15,17-tetrakis(triisopropylsilylethynyl)heptacene was obtained by a Pd-catalyzed reaction of a 2,3-diamino-1,4-diethynylanthracene with a 2,3-dibromo-1,4-diethynyl anthracene. Positioning the TIPS-ethynyl groups adjacent to the central ring suppresses dimerization via...
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| Main Authors: | , , , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
6 March 2024
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| In: |
Journal of the American Chemical Society
Year: 2024, Volume: 146, Issue: 9, Pages: 5793-5798 |
| ISSN: | 1520-5126 |
| DOI: | 10.1021/jacs.3c13629 |
| Online Access: | Verlag, kostenfrei, Volltext: https://doi.org/10.1021/jacs.3c13629
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| Author Notes: | Wansheng Zong, Nikolai Hippchen, Nico Zeitter, Steffen Maier, Philipp Ludwig, Frank Rominger, Jan Freudenberg, and Uwe H.F. Bunz |
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| 520 | |a The symmetrical 7,16-diaza-6,8,15,17-tetrakis(triisopropylsilylethynyl)heptacene was obtained by a Pd-catalyzed reaction of a 2,3-diamino-1,4-diethynylanthracene with a 2,3-dibromo-1,4-diethynyl anthracene. Positioning the TIPS-ethynyl groups adjacent to the central ring suppresses dimerization via [4+4] cycloadditions and Diels-Alder reactions; the middle pyrazine ring renders this species stable to oxidation. A single crystal structure was obtained, and thin film transistors with μn = 0.042 cm2 V-1 s-1 were produced. Transposition of the alkynyl groups into the 5,8,15,18-positions with a quinoxaline unit in the center of the heptacene decreases the stability, as does the introduction of two more nitrogen atoms into the 5,18-positions. The hydrocarbon 6,8,15,17-tetrakis(triisopropylsilylethynyl)heptacene is reasonably stable with a half-life of 25 h in solution. Four correctly placed TIPS-ethynyl groups protect heptacene cores. | ||
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