Many diketopyrrolopyrrole-based (DPP) polymers have shown remarkable transport properties and to fabricate cost efficient materials, the new direct (hetero)arylation polymerization (DHAP) could become a valuable tool. Although the DHAP offers great promise for more efficient, atom-economic and cheaper aromatic C-C bond formations, this method seems to involve a lack of selectivity. Recently, we reported an alternating DPP-based copolymer prepared by DHAP that shows a well-defined structure. A rational side-chain design of the comonomers led to a polymer that exhibits a high molecular weight along with excellent charge transport properties (p-type mobility up to 1.17 cm2/V•s). A near ideal transfer curve was found, from the quasi-linear slope, implying a high quality semiconductor. These results suggest that couplings involving only (hetero)aromatic units in DHAP could be more selective than expected. We are currently expanding our scope to a thiophene-based electron-rich moiety bearing multiples reactive C-H bonds. Despite reports pointing to a low selectivity from energetic considerations on the desired C-H bond, preliminary results showed that in the right conditions, one can obtain the wished homopolymer in good yield. No evidence branching structure were found leading to well-defined polymer, no directing groups were used. From these results, it is possible to believe in a near future that the DHAP will become as reliable as current organometallic couplings in π-conjugated polymer synthesis.