INERENENTLY CHIRAL MULTIFUNCTIONAL ORGANIC SEMICONDUCTORS

The availability of materials which could couple electroactivity properties and enantiorecognition capability is an ambitious objective of the modern chemical research. Chirality is generally introduced in the polymer by attaching chiral pendants to the electroactive conjugated backbone through suitable linkers and a great variety of substituents have been employed either chosen from the chiral pool, like sugar and amino-acids, or man-made, designed and synthesized for specific applications. We have planned to develope a new strategy by preparing polymerizable chiral oligothiophene monomers in which chirality results from a tailored torsion produced in the oligothiophene backbone by introducing in the monomer structure an atropisomeric scaffold.1 The structural design of the monomers requires also that the polymerization sites of the monomers would be homotopic, thus granting the perfect constitutional regularity of the polymers. The 2,2’-bis(2,2’-bithiophene-5-yl)-3,3’-bithianaphthene is the first example of this strategy; the antipodes have been recently obtained in an enantiopure state and submitted to the electropolymerization process yielding materials exhibiting outstanding chirality manifestations.