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In the organic electronics research field, several strategies have been used to modulate the transport properties of thiophene-derived semiconductors via sequential functionalization of their π-conjugated cores. This review summarizes the major design and synthetic strategies for tuning thiophene-containing small molecule and polymer properties by introducing electron-deficient nitrogen-containing azine and azole moieties. Several examples are presented which elucidate the structural, optical, and electronic consequences of incorporating these electron-deficient fragments in the conjugated skeletons, particularly relating to applications in organic thin-film transistors.