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Introducing <jats:italic>ortho<\/jats:italic>\u2010anisole at C\u20102 resulted in deep blue emitters in solution, with quantum yields up to 74\u2009%. On the other hand, when <jats:italic>ortho<\/jats:italic>\u2010phenol was introduced, forming a strong hydrogen bond with the pyridine nitrogen, excited\u2010state intramolecular proton transfer was witnessed by the dual emission of the fluorophores, which is sensitive to the dye environment. The phenyl ring at C\u20104 was used to introduce electron\u2010donating or withdrawing groups, to fine\u2010tune the photophysical properties of the dyes. Crystal structures of the fluorophores, together with theoretical studies using DFT\/TD\u2010DFT calculations, were used to rationalize the experimental photophysical properties of the two families of dyes. 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