Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 41, Pages 16342-16345Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja206060n
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Funding
- MEXT [22000008, 20685005]
- JST
- JSPS [P 09046]
- Global COE Program for Chemistry Innovation
- Grants-in-Aid for Scientific Research [22000008, 20685005] Funding Source: KAKEN
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A heptacyclic carbocycle possessing three p-quinodimethane units conjugated in one plane has been synthesized and shown to exhibit distinct biradical characteristics. The molecule has a HOMO/LUMO band gap of ca. 1 eV and a S(0)-T(1) energy gap of 2.12 kcal/mol, and it absorbs and emits near-IR light at room temperature. It is air-stable under ambient light for several months and thermally stable up to 160 degrees C under nitrogen, and it undergoes reversible two-electron oxidation and reduction. The synthetic approach is such that a smaller and larger oligo-p-quinodimethane can be synthesized.
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