The　6H-[1,2,5]thiadiazolo[3,4-e]thieno[3,2-b]indole-flanked　para-azaquinodimethane　(p-AQM)-based　polymer　semiconductors　PQ-1　and　PQ-2　are　rationally　designed　through　a　π-extended　aromatic-quinoidal　design　strategy.　They　are　synthesized　by　the　direct　arylation　polycondensation　(DArP)　method.　Their　physicochemical　properties　are　investigated.　Both　polymers　show　high　number-average　molecular　weights　of　over　120　kDa.　PQ-1　exhibits　a　narrower　band　gap　compared　to　its　thiophene-flanked　p-AQM　polymer　counterpart.　PQ-2,　with　more　aromatic　thiophene　units　in　the　conjugated　main　chains,　displays　a　broader　band　gap　compared　to　PQ-1.　Both　PQ-1　and　PQ-2　possess　high-lying　highest　occupied　molecular　orbital　energy　levels　(about　−5.0　eV).　They　exhibit　typical　p-type　semiconductor　characteristics　according　to　the　results　of　characterization　of　organic　field-effect　transistors.　This　work　presents　an　alternative　π-extended　aromatic-quinoidal　design　strategy　and　a　convenient　DArP　method　to　build　new　p-AQM　polymer　semiconductors.　©　2023　RSC.