Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 41, Pages 17662-17669Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c08274
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Funding
- National Natural Science Foundation of China (NSFC) [21771011, 21875006]
- National Key Research and Development Program of China [2019YFA0708502]
- U.S. Department of Energy (DOE) Office of Science User Facility [DE-AC02-05CH11231]
- J-PARC user programs [2018B0249, 2018BF2106]
- U.S. NSF [DMR-1644779]
- State of Florida
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Solid-state topochemical polymerization (SSTP) is a promising method to construct functional crystalline polymeric materials, but in contrast to various reactions that happen in solution, only very limited types of SSTP reactions are reported. Diels-Alder (DA) and dehydro-DA (DDA) reactions are textbook reactions for preparing six-membered rings in solution but are scarcely seen in solid-state synthesis. Here, using multiple cutting-edge techniques, we demonstrate that the solid 1,4-diphenylbuta-diyne (DPB) undergoes a DDA reaction under 10-20 GPa with the phenyl as the dienophile. The crystal structure at the critical pressure shows that this reaction is distance-selected. The distance of 3.2 angstrom between the phenyl and the phenylethynyl facilitates the DDA reaction, while the distances for other DDA and 1,4-addition reactions are too large to allow the bonding. The obtained products are crystalline armchair graphitic nanoribbons, and hence our studies open a new route to construct the crystalline carbon materials with atomic-scale control.
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