Crystal structure consisting both of segregated and mixed donor-acceptor columns

Chemistry Letters

Volumn , Issue 11, 2001, Pages 1144-1145

  Otsuki, Joe ^a   Matsui, Hiroyuki ^a   Imamura, Koichiro ^a   Yoshikawa, Isao ^b   Araki, Koji ^b   Seno, Manabu ^a  

^a NIHON UNIVERSITY   (Japan)

^b INSTITUTE OF INDUSTRIAL SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035541207     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.1144     Document Type: Article

References (24)

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14. In the cocrystal of bis-anthracene 1 and TCNQ, the anthraquinone spacer comes next to an anthracene arm of a different molecule, generating stacked columns consisting of the repetition of [anthracene-TCNQ-anthracene -anthraquinone]. In terms of a DA viewpoint, it may be represented as [D-A-D-A′].
15. +].
16. 2 in an H-shaped glass vessel. The TCNQ was placed in one of the legs of the vessel and 2 in the other.
17. 2)).
18. M. Bailey, Acta Crystallogr., 11, 103 (1958); C. J. Brown and M. L. Colclough, Acta Crystallogr., C39, 300 (1983); D. Hall and C. L. Nobbs, Acta Crystallogr., 21, 927 (1966).
19. M. Bailey, Acta Crystallogr., 11, 103 (1958); C. J. Brown and M. L. Colclough, Acta Crystallogr., C39, 300 (1983); D. Hall and C. L. Nobbs, Acta Crystallogr., 21, 927 (1966).
20. M. Bailey, Acta Crystallogr., 11, 103 (1958); C. J. Brown and M. L. Colclough, Acta Crystallogr., C39, 300 (1983); D. Hall and C. L. Nobbs, Acta Crystallogr., 21, 927 (1966).
21. MOPAC calculations (Sony Tektronix, CAChe) with PM3 parameters show that the acridine arm has a dipole moment of 2.1 debye, directing from the nitrogen atom to C-9. The anthraquinone spacer also has a dipole moment of 2.0 debye. However, its orientation is not optimum for the stacking due to the distortion; the dipole roughly directs from quinoid C-10 to one of ether oxygens, depending on the distortion.
22. The ionization potentials are 7.45 and 7.8 eV for anthracene and acridine, respectively: "Kagaku Binran Kisohen II," 4th ed., ed. by Chemical Society of Japan., Maruzen, Tokyo (1993).
23. 2 molecules dissociate from the crystal at 123-134 °C.
24. L. R. Melby, R. J. Harder, W. R. Hertler, W. Mahler, R. E. Benson, and W. E. Mochel, J. Am. Chem. Soc., 84, 3374 (1962).