Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 37, Pages 15351-15356Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja3043883
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Funding
- National Science Foundation [DMR-1005810]
- Center for Excitonics, an Energy Frontier Research Center
- U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences [DE-SC0001088]
- Direct For Mathematical & Physical Scien
- Division Of Materials Research [1005810] Funding Source: National Science Foundation
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Synthesis of a new class of fully unsaturated ladder structures, phenylene-containing oligoacenes (POAs), using 3,4-bis(methylene)cyclobutene as a building block for sequential Diels-Alder reactions is described. The geometric effects of strain and energetic cost of antiaromaticity can be observed via the optical and electrochemical properties of the reported compounds. The resulting shape-persistant ladder structures contain neighboring chromophores that are partially electronically isolated from one another while still undergoing a reduction in the band gap of the material.
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