Novel push-pull π-conjugated compounds suffering steric hindrance between donor and acceptor subunits

Tetrahedron Letters

Volumn 49, Issue 28, 2008, Pages 4342-4345

  Masuda, Daisuke ^a   Wakabayashi, Hidetsugu ^a   Miyamae, Hiroshi ^a   Teramae, Hiroyuki ^a   Kobayashi, Keiji ^a  

^a JOSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BIS(DICYANOMETHYLENE)INDAN 2 YLIDENE; ACETONITRILE; CARBON; CHLOROFORM; INDAN DERIVATIVE; METHYL GROUP;

ARTICLE; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; STEREOSPECIFICITY; TEMPERATURE SENSITIVITY; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 44649163213     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.035     Document Type: Article

References (25)

1. Nalwa H.S. Adv. Mater. 5 (1993) 341
2. Long N.J. Angew. Chem., Int. Ed. 34 (1995) 21
3. Denning R.G. J. Mater. Chem. 5 (1995) 365
4. Verbiest T., Houbrechts S., Kauranen M., Clays K., and Persoons A. J. Mater. Chem. 7 (1997) 2175
5. Wong W.S., Bossard C., and Gunter P. Adv. Mater. 9 (1997) 837
6. For recent example, see:. Kivala M., Boudon C., Gisselbrecht J.-P., Seiler P., Gross M., and Diederich F. Angew. Chem., Int. Ed. 46 (2007) 6357
7. Alias S., Andreu R., Cerdan M.A., Franco S., Garin J., Orduna J., Romero P., and Villacampa B. Tetrahedron Lett. 48 (2007) 6539
8. Alias S., Andreu R., Blesa M.J., Franco S., Garin J., Gragera A., Orduna J., Romero P., Villacampa B., and Allain M. J. Org. Chem. 72 (2007) 6440
9. Morioka Y., Yoshizawa N., Nishida J., and Yamashita Y. Chem. Lett. 33 (2004) 1190
10. Moore A., Chesney A., Bryce M.R., Batsanov A.S., Kelly J.F., Howard J.A.K., Perepichka I.F., Perepichka D.F., Meshulam G., Berkovic G., Kotler Z., Mazor R., and Khodorkovsky V. Eur. J. Org. Chem. (2001) 2671
11. For recent example, see:. Andreu R., Blesa M.J., Carrasquer L., Garin J., Orduna J., Villacampa B., Alcala R., Casado J., Ruiz D., Mari C., Lopez N.J.T., and Allain M. J. Am. Chem. Soc. 127 (2005) 8835
12. Sato N., Kawamoto I., Sakuma T., Silinsh E.A., and Jurgis A.J. Mol. Cryst. Liq. Cryst. 333 (1999) 243
13. Ashwell G.J., Dyer A.N., Green A., Sato N., and Sakuma T. J. Mater. Chem. 10 (2000) 2473
14. Heynderickx A., Kaou A.M., Moustrou C., Samat A., and Guglielmetti R. New J. Chem. 27 (2003) 1425
15. Inoue S., Mikami S., Takimiya K., Otsubo T., and Aso Y. Heterocycles 71 (2007) 253
16. Takahashi T., Takimiya K., Otsubo T., and Aso Y. Org. Lett. 7 (2005) 4313
17. For recent example, see:. Bastanov A.S., Bryce M.R., Coffin M.A., Green A., Hester R.E., Howard J.A.K., Lednev I.K., Martin N., Moore A.J., Moore J.N., Orti E., Sanchez L., Saviron M., Viruela P.M., Viruela R., and Ye T.-Q. Chem. Eur. J. 4 (1998) 2580
18. Gompper R., Wagner H.-U., and Kutter E.. Chem. Ber. 101 (1968) 4123
19. For the D-A molecules designed by the use of 1,3-indandione skelton as an acceptor subunit, see:. Andreu R., Aramburo J., Cerdan M.A., Garin J., Orduna J., and Villacampa B. Tetrahedron Lett. 47 (2006) 661
20. Nishiyabu R., and Anzenbacher Jr. P. Org. Lett. 8 (2006) 359
21. One-step synthesis of 1 from 1,3-bis(dicyanomethylene)-2-indanone and benzodithiolylium tetrafluoroborate was also carried out, but the yields were not improved.
22. 3, Z = 2, R = 0.0382, Rw = 0.0557, GOF = 1.097.
23. 3, Z = 4, R = 0.0392, Rw = 0.0718, GOF = 1.067.
24. Crystallographic data for the structural analysis of 1 and 2 have been deposited with the Cambridge Crystallographic Data Centre ( CCDC 679925 for 1 and 679926 for 2). These data can be obtained free of charge via www.ccds.cam.au.uk/conts/retrieving.html.
25. In the preparation of 2 and 3, their isomer, in which the ester group is directed to the benzo-1,3-dithiol-2-ylidene moiety, could not be isolated.