Abstract The synthesis of naphthalenyl-cored O-doped small molecule electrochromes was achieved. In a single intramolecular Pummerer oxidative cycloetherification reaction, dipyrano, difurano, and furano-pyrano products could be obtained. All molecules showed p-type semiconducting and electrochromic properties, with the colour of the transition being dependent on the O-ring. Abstract In this work, we report the synthesis of O-doped naphthalene-based electrochromes.