4,7-Bis(2-thienylethynyl)-2,1,3-benzothiadiazole was prepared by Sonogashira coupling. The crystal structure showed that one thiophene ring is coplanar and the other is perpendicular to the benzothiadiazole ring.
MartinR.E. and DiederichF., Angew. Chem. Int. Ed. Engl.1999, 38, 1350.
3.
Eds AviramA. and RatnerM., Annals of the New York Academy of Sciences Vol. 852: Molecular Electronics, Science and Technology, The New York Academy of Sciences, New York, 1998.
4.
(a) KarikomiM., KitamuraC., TanakaS. and YamashitaY., J. Am. Chem. Soc.1995, 117, 6791
5.
KitamuraC., TanakaS. and YamashitaY., Chem. Mater.1996, 8, 570.
6.
Recent small HOMO-LUMO gap molecules, see: (a) van MullekomH.A.M., VekemansJ.A.J.M. and MeijerE.W., Chem. Eur. J., 1998, 4, 1235
7.
RaimundoJ.-M., BlanchardP., BrissetH., AkoudadS. and RoncaliJ., Chem. Commun., 2000, 939
8.
MitschkeU., DebaerdemaekerT. and BäuerleP., Eur. J. Org. Chem., 2000, 425.
9.
SonogashiraK., In Metal-catalyzed Cross-coupling Reactions, eds DiederichF. and StangP.J., Wiley-VCH, Weinheim, 1998. p. 203.
10.
PilgramK., ZupanM. and SkilesR., J. Heterocycl. Chem.1970, 7, 629.
11.
SarkarA., SekherP., KamathM. B., BhagwatL., BabuK.N., RajalakshimiK. and TalwarS., Ind. J. Chem. 1991, 30B, 360.
12.
ThorandS. and KrauseN., J. Org. Chem. 1998, 63, 8551.
13.
The reaction did not proceed smoothly. 4% of a mono-coupling compound was also isolated as a by-product.In the reaction, the catalytic activity disappeared within 2 h and the starting materials were not consumed completely, though we searched various experimental conditions. This finding may be ascribed to catalytic poison effect of 2,1,3-benzothiadiazole unit.
14.
For example, absorption maxima of 16-mers of oligo(phenylene ethynylene) and oligo(thiophene ethynylene) were 376 and 433 nm, respectively: (a) SchummJ. S., PearsonD. L. and TourJ.M., Angew. Chem. Int. Ed. Engl., 1994, 33, 1360
SIR92: AltomareA., BurlaM.C., CamalliM., CascarampM., GiacovazzaoM.C., GuagliardiA. and PolidoriG., J. Appl. Cryst., 1994, 27, 435.
17.
DIRDIF94: BeurskensP.T., AdmiraalG., BeurskensG., BosmanW.P., de GelderR., IsraelR. and SmitsJ.M.M., The DIRDIF94 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands, 1994.
