Practical one-step synthesis of symmetrical liquid crystalline dialkyloligothiophenes for molecular electronic applications

Chemistry Letters

Volumn 35, Issue 2, 2006, Pages 166-167

  Leroy, Julie ^a   Levin, Jeremy ^a   Sergeyev, Sergey ^a   Geerts, Yves ^a  

^a UNIVERSITÉ LIBRE DE BRUXELLES   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646438438     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2006.166     Document Type: Article

References (22)

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21. Alkylation of terthiophene (general procedure): A solution of 2,2′:5′,2″-terthiophene (5) (500mg, 2.12 mmol) in 10 mL of dry THF was cooled to -78 °C, and a solution of n-BuLi (ca. 1.6 M in hexane, 6.04 mmol) was added dropwise via cannula. The reaction mixture was stirred for 10 min at -78°C, then a solution of t-BuOK (1.0 M in THF, 8.05 mmol) in THF was added. The stirring was continued for 15 min at -78°C, then the 1-iodoalkane (4.24 mmol) was added. The reaction mixture was allowed to slowly reach room temperature and stirred overnight, quenched by slow addition of water (10 mL) and extracted with hexane (3 × 10 mL). After evaporation of solvent the residue was purified by column chromatography or crystallized from methanol/toluene to give pure 2a-2e. Supporting Information contains analytical data of synthesized compounds.
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