Journal
NATURE CHEMISTRY
Volume 10, Issue 8, Pages 838-844Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/s41557-018-0075-y
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Funding
- US Department of Health and Human Services (National Institute of General Medical Sciences) [R35 GM-127097]
- National Science Foundation [CHE-1665389]
- NIH Shared Instrumentation Grant program [S10OD011952]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R35GM127097, R01GM065597] Funding Source: NIH RePORTER
- OFFICE OF THE DIRECTOR, NATIONAL INSTITUTES OF HEALTH [S10OD011952] Funding Source: NIH RePORTER
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Polyacenes are organic compounds that have multiple, fused, aromatic rings. These highly conjugated molecules often have interesting photonic and/or electronic properties that afford them the potential for application in a host of organoelectronic devices such as sensors, light-emitting diodes, photovoltaic devices and field-effect transistors. Here, we show the development and use of the domino hexadehydro-Diels-Alder reaction to synthesize structurally diverse polyacenes from acyclic polyyne precursors. The key event in these transformations is the successive reaction of multiple 1,3-butadiyne units with a series of in-situ-generated, diynophilic arynes. The polyyne substrates were designed to allow for rapid engagement of each progressively larger aryne following the initiating (and ratelimiting) production of the first reactive intermediate-the benzyne. We show that aryne-trapping reactions are broad in scope and that these cascade or domino processes can be quite efficient.
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