Inherently chiral oligothiophenes with outstanding enantioselection performances

Linear conjugated oligo-thiophenes of variable length and different substitution pattern are ubiquitous in technologically advanced opto-electronic devices, though limitations in application derive from insolubility, scarce processability and chain-ends effects. The paper describes an easy access to chiral oligothiophenes of non-conventional design constituted by 12 and 18 fully conjugated thiophene units. Chemical oxidation of "inherently chiral" sexithiophene monomers, displaying the general structure 1 (Scheme 1), synthesized from commercially available materials, induces the formation of dimers and trimers of unexpected structure. Combination of chirality with electroactivity makes these molecules unique in the current literature. These oligothiophenes, which are stable and soluble in most organic solvents, show outstanding chiroptical properties, high Circularly Polarized Luminescence effects and an exceptional enantiorecognition ability.