Towards the synthesis of mono- and bi-functional amphiphilic oligothiophenes: organic materials for opto-electronic applications

In this report, we describe our initial synthesis and characterization of mono-functional and bi-functional dibromoalkyl oligothiophenes to achieve amphiphilicity and telechelic functionality. Oligothiophenes are an important class of organic materials for opto-electronic devices and display applications. We have mono-functionalized oligothiophenes by the synthesis of a quinquethiophene bromoalkyl derivative. A bi-functional sexithiophene was derived primarily by the symmetrical coupling of terthiophene derivatives. Both were synthesized using Grignard coupling and lithiation reaction methodologies. UV-Vis, IR, NMR, MALDI-TOF-MS, and DSC confirmed the structure and physical properties of the oligomers. In addition, we have also synthesized an amphiphilic diamine derivative from the reaction of hexamethylenediamine with a bromoalkyl terthiophene derivative. Using photoluminescence, the photophysical properties of the oligomers were found to be that of typical oligothiophenes. Processing as ultrathin films for devices is currently being investigated.