New π-conjugated system with a rigid framework of 1,8-anthrylene - Ethynylene cyclic dimer and its monoanthraquinone analogue

Organic Letters

Volumn 9, Issue 18, 2007, Pages 3655-3658

  Toyota, Shinji ^a   Kurokawa, Megumi ^a   Araki, Mai ^a   Nakamura, Kazuya ^a   Iwanaga, Tetsuo ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34548534840     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701541q     Document Type: Article

References (26)

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19. Goichi, M.; Segawa, K.; Suzuki, S.; Toyota, S. Synthesis 2005, 2116.
20. For the synthesis of 3, the coupling of l-ethynyl-8-iodo-10-iso- propylanthracene afforded a trace amount of the desired product.
21. 3, d) 23.4, 28.7, 92.4, 93.8, 182.5, 184.6 and 14 aromatic signals.
22. -1, T = 273 K, number of data 5818, number of data used 5008 (1 > 2.0σ(I)), R1 = 0.052, wR2 = 0.131, GOF 0.976, CCDC 654616.
23. The same type of deformations were reported for some anthraquinone derivatives. For example, the folding angle was 14.1° for O9 in 1,8-dinitroanthraquinone. Becker, H.-D.; Becker, H.-Ch.; Langer, V. Z. Kristallogr. 1996, 211, 319.
24. Selected data of interlayer distances for anthracene-arene complexes. 2,3,5,6-Tetrachloro-1,4-dicyanobenzene 3.43 Å: Britton, D. Acta Crystallogr. 2005, E61, o1707. 2,7-Dinitroanthraquinone 3.42 Å and 1,8-dinitroanthraquinone 3.48 Å: ref 12.
25. Breitmaier, E.; Voelter, W. Carbon-13 NMR Spectroscopy; VCH: New York, 1990; Chapter 4.3.
26. Connors, K. A. Binding Constants; John Wiley & Sons: New York, 1987; Chapter 5. Higher order association is unlikely in this case because the deformed carbonyl oxygen blocks the other side of the plane.