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The Most Stable and Fully Characterized Functionalized Heptacene^†

Doris Chun

Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095-1569 (USA)

Department of Chemistry and Biochemistry 9510, University of California, Santa Barbara, CA 93106-9510 (USA), Fax: (+1) 805-893-4120 www.chem.ucsb.edu/

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Yang Cheng Dr.,

Yang Cheng Dr.

Department of Chemistry and Biochemistry 9510, University of California, Santa Barbara, CA 93106-9510 (USA), Fax: (+1) 805-893-4120 www.chem.ucsb.edu/

Current Address: Core Research & Development, The Dow Chemical Company, Midland, MI 48674 (USA)

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Fred Wudl Prof. Dr.,

Fred Wudl Prof. Dr.

[email protected]

Department of Chemistry and Biochemistry 9510, University of California, Santa Barbara, CA 93106-9510 (USA), Fax: (+1) 805-893-4120 www.chem.ucsb.edu/

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Doris Chun,

Doris Chun

Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095-1569 (USA)

Department of Chemistry and Biochemistry 9510, University of California, Santa Barbara, CA 93106-9510 (USA), Fax: (+1) 805-893-4120 www.chem.ucsb.edu/

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Yang Cheng Dr.,

Yang Cheng Dr.

Department of Chemistry and Biochemistry 9510, University of California, Santa Barbara, CA 93106-9510 (USA), Fax: (+1) 805-893-4120 www.chem.ucsb.edu/

Current Address: Core Research & Development, The Dow Chemical Company, Midland, MI 48674 (USA)

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Fred Wudl Prof. Dr.,

Fred Wudl Prof. Dr.

[email protected]

Department of Chemistry and Biochemistry 9510, University of California, Santa Barbara, CA 93106-9510 (USA), Fax: (+1) 805-893-4120 www.chem.ucsb.edu/

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First published: 15 October 2008

https://doi.org/10.1002/anie.200803345

Citations: 247

^†

We are indebted to Dr. Guan Wu for his assistance with the single-crystal structure elucidation. We thank Prof. John Anthony for providing valuable insight and data that helped facilitate our characterization. We also thank Prof. Galen Stucky for helpful suggestions which led to the successful collection of the X-ray data and Brittnee Veldman for technical assistance with the UV/Vis–NIR data. This work was funded by the NSF through grant DMR 9796302.

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Graphical Abstract

Lucky seven: Crystals of heptacene, which consists of seven linearly fused benzene rings, remain stable for at least 21 days in mineral oil and 24 h in degassed solution when the oligoacene is functionalized with phenyl and triisopropylsilylethynyl groups (see scheme). The right combination of functionalities makes this seven-ring system the most stable functionalized heptacene synthesized to date.

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Volume47, Issue44

October 20, 2008

Pages 8380-8385

The Most Stable and Fully Characterized Functionalized Heptacene^†

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The Most Stable and Fully Characterized Functionalized Heptacene^†