The continued development of new components for use within conducting organic electronic systems is of great importance. While there are high efficiency materials with PCE in the 11% range, their synthetic complexity leads to high costs of manufacturing which prevent widespread application. The demand for materials which possess high performance coupled with a readily scalable synthetic route lead to our examination of naphtho[1,2-b:5,6-b’]difuran (NDF) as a promising electron donating unit for use in organic photovoltaic materials. While there is extensive work published on various benzodichalcogen motifs (BDF, BDT, BDSe), their naphtho- variants have seen little exploration until recently. These naphtho- systems boast a larger pi-conjugated surface than their direct benzo- counterparts; a key characteristic that is associated with enhanced interchain interactions, higher charge-mobilities, and more ordered morphologies in the solid state. NDF stood out to us as a particularly exciting system due to the exceptional degree of planarity that the system should exhibit coupled with its high electron density. NDF based small molecules have seen use in FETs which exhibited high hole mobilities, and limited reports of its use in OPV materials show potential for a system that exhibits both good performance and the potential for synthesis via new C-H activation polymerization conditions to facilitate more scalable syntheses. We have synthesized conjugated polymers containing NDF as a donor unit and various diketopyrrolopyrroles (DPP) as acceptor units. Additionally, these polymers were obtained via C-H activation polymerization utilizing an affordable catalytic system compared to traditional Pd-catalyzed cross-coupling methodologies. The polymers exhibited good molecular weights along with narrow bandgaps featuring absorption maxima at or beyond 650nm in the solid state. The potential of this donor unit will be further explored using additional acceptor units in future work in addition to exploring the development of small molecules based on similar C-H activation couplings.

Investigating naphtho[1,2-b:5,6-b’]difuran (NDF) as an electron rich co-monomer in donor-acceptor conjugated polymer systems utilizing C-H activation polymerization

256th National Meeting (2018)

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