Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 15, Pages 7658-7663Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo401200m
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan
- Japan Prize Foundation
- Grants-in-Aid for Scientific Research [25870112, 24550040] Funding Source: KAKEN
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Hexadecadehydrodibenzo[20]-, tetracosadehydrotribenzo[30]-, and dotriacontadehydrotetrabenzo[40]annulene derivatives ([20]-, [30]-, and [40]DBAs) possessing tetrayne linkages were synthesized. X-ray diffraction analysis demonstrated that the molecules of [30]DBA and p-xylene form a 2D sheetlike structure. Planar [20]- and [30]DBAs show significantly weak or almost no tropicity. The extension of the acetylenic linkages from a diyne to a tetrayne unit narrows HOMO-LUMO gaps. The self-association behavior of [30]DBA in solution resulting from effective pi-pi stacking interactions was observed.
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