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This photochromic dyad can be switched reversibly by UV\u2010light irradiation of its ring\u2010open form <jats:bold>3\u2009o<\/jats:bold> leading to the ring\u2010closed form <jats:bold>3\u2009c<\/jats:bold>, and back reaction of <jats:bold>3\u2009c<\/jats:bold> to <jats:bold>3\u2009o<\/jats:bold> by irradiation with visible light. Solvent\u2010dependent fluorescence studies revealed that the emission of ring\u2010closed form <jats:bold>3\u2009c<\/jats:bold> is drastically quenched in solvents of medium (e.g., chloroform) to high (e.g., acetone) polarities, while the emission of the ring\u2010open form <jats:bold>3\u2009o<\/jats:bold> is appreciably quenched only in highly polar solvents like DMF. The strong fluorescence quenching of <jats:bold>3\u2009c<\/jats:bold> is attributed to a photoinduced electron\u2010transfer (PET) process from the excited PBI unit to ring\u2010closed DAE moiety, as this process is thermodynamically highly favorable with a Gibbs free energy value of \u22120.34\u2005eV in dichloromethane. The electron\u2010transfer mechanism for the fluorescence quenching of ring\u2010closed <jats:bold>3\u2009c<\/jats:bold> is substantiated by ultrafast transient measurements in dichloromethane and acetone, revealing stabilization of charge\u2010separated states of <jats:bold>3\u2009c<\/jats:bold> in these solvents. 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