Oligothiophenes synthesis

Afzali, A., Breen, T.L., and Kagan, C.R., An efficient synthesis of symmetrical oligothiophenes Synthesis and transport properties of a soluble sexithiophene derivative, Chem. Mater. 14, 1742-1746, 2002. 

Tsivgoulis GM, Lehn J-M (1996) Photoswitched tuid functionalized oligothiophenes synthesis and photochemical and electrochemical properties. Chem Eur J 2 1399-1406. doi 10.1002/ chem. 19960021112... 

For nonexhaustive recent examples of oligothiophenes synthesis via Stille coupling see H. Yu, B. Xu, T. M. Swager,... 

An interesting application of the Paal thiophene synthesis was documented for the synthesis of a polystyrene-oligothiophene-polystyrene copolymer. In the Stetter reaction of aldehyde 13 and P-dimethylaminoketone 14, in situ generation of the a,p-unsaturated ketone preceded nucleophilic 1,4-conjugate addition by the acyl anion... 

In addition, highly enantioselective nitroaldol reactions were performed by Bandini et al. by using a new class of C2-symmetric oligothiophene ligands, in 2007. Thus, associated to copper, these C2-symmetric bis(amino) ligands allowed the synthesis of a wide range of enantiomerically enriched nitroalcohols... 

A recent publication by the group of Barbarella has disclosed the rapid preparation of poorly soluble unsubstituted and modified a-quinque- and sexithiophenes by the extensive use of bromination/iodination steps and microwave-assisted Suzuki and Sonogashira cross-couplings (Scheme 6.16) [42]. Suzuki reactions were either carried out under solvent-free conditions on a strongly basic potassium fluoride/ alumina support for the synthesis of soluble oligothiophenes, or in solution phase for the preparation of the rather insoluble a-quinque- and sexithiophenes. In both cases, 5 mol% of [l,l -bis(diphenylphosphino)ferrocene]dichloropalladium(II)... 

Scheme 6.16 Synthesis of oligothiophenes using Suzuki cross-coupling reactions.

G. Barbarella, L. Favaretto, G. Sotgiu, M. Zambianchi, L. Antolini, O. Pudova, and A. Bongini, Oligothiophene 5,5-dioxides. Synthesis and electronic properties in relation to the parent oli-gothiophenes, J. Org. Chem., 63 5497-5506, 1998. 

K.Y. Musick, Q.-S. Hu, and L. Pu, Synthesis of binaphthyl-oligothiophene copolymers with emissions of different colors systematically tuning the photoluminescence of conjugated polymers, Macromolecules, 31 2933-2942, 1998. 

H. Meng and W. Huang, Novel photoluminescent polymers containing oligothiophene and /u-phenylene-1,3,4-oxadiazole moieties synthesis and spectroscopic and electrochemical studies, J. Org. Chem., 65 3894-3901, 2000. 

Figure 7.16 (A) Dendron-capped poly(triacetylene) and, (B) soluble oligothiophenes obtained by dendrimers assisted synthesis...

A. Rajca, M. Miyasaka, M. Pink, H. Wang, S. Rajca, Helically Annelated and Cross-conjugated Oligothiophenes Asymmetric Synthesis, Resolution and Characterization of a Carbon-Sulfur [7]Helicene, J. Am. Chem. Soc. 2004, 126, 15211-15222. 

Another germanium-based hnker has been developed for solid-phase synthesis of a pyrazole hbrary [79]. A new iterative synthesis of regioregular oligothiophenes has been developed in which double-couphng after each iteration minimizes deletion sequences. The method exploits the susceptibility of a-silyl- but not a-ger-myl-substituted thiophene derivatives towards nucleophilic ipso protodemetalation and features an unusual base-free Suzuki-type coupling product. The strategy... 

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