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Org Lett. 2001 Jul 26;3(15):2379-82.

Synthesis and chiroptical properties of optically active, regioregular oligothiophenes.

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  • 1Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan.


[reaction: see text] A series of regioregular oligothiophenes bearing chiral oxazoline residues have been synthesized in high yields by a stepwise synthesis using the Stille cross-coupling reaction. The chiroptical properties of the oligothiophenes up to the octamer were investigated with UV-visible and CD spectroscopies. The octamer showed split-type Cotton effects in chloroform as a good solvent in the presence of a poor solvent such as acetonitrile, while the lower molecular weight oligomers exhibited almost no induced CD.

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