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Largely π-extended rylene diimide-fused thienoacenes, a new family of fully fused electron donor-acceptor (D-A) molecules, have been readily synthesized by a novel trisulfur radical anion (S 3 ˙ - )-triggered stitching thienannulation strategy. The ladder-type fused thiophene cores are constructed in a stitching manner through multiple carbon-sulfur bond formation between acetylenic rylene dyes and S 3 ˙ - . A detailed mechanistic study of these stitching thienannulations unveiled the multiple reactivities of S 3 ˙ - . Physical properties of the newly formed D-A, A-D-A, and D-A-D type thienoacenes have also been investigated, which revealed their precisely controllable electronic properties., Competing Interests: There are no conflicts to declare., (This journal is © The Royal Society of Chemistry.)