The unique optoelectrical properties and good thermo- and photo-stability of diketopyrrolopyrrole (DPP)-based compounds have resulted in their extensive utilization in organic semconductive materials. Several applications of organic field effect transistors (OFETs), organic photovoltaics (OPVs), organic light emitting diodes (OLEDs), and dye-sensitized solar cells (DSSC) are reported annually. Our work presents an unprecedented and efficient synthesis of a new DPP scaffold, 2,5-dibutyl-3,6-dimethyl-1H,2H,4H,5H-pyrrolo[3,4-c]pyrrole-1,4-dione (DMDPP) that can’t be attained through the conventional synthetic route. Due to the electron-deficient nature of DPP, the H atoms at the DPP-flanked methyl groups are remarkably acidic, which make them highly reactive. Consequently, we have functionalized the methyl group of DMDPP using an Aldol-like condensation to prepare vinyl- flanked DPP materials as small molecules and polymers. This functionalization is in sharp contrast to the ubiquitous transition-metal coupling methods. More interestingly, the two hydrogen atoms of the vinyl groups can interact with both of the two O atoms of DPP ring, and the adjacent hetero atoms of the p-partner by non-classical intramolecular hydrogen bonding. This interaction makes the pi-conjugated system more coplanar and should facilitate improvement in the charge carrier mobility of the organic semi-conductive material. This work provides us the opportunity to reach 3,6-divinyl substituted DPP compounds that are of interest to material community

Unprecedented and efficient synthesis of DMDPP and its conversion to the arylalkenyl π-system through C-H transition-metal-free approach

2019 Fall National Meeting

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.