blue emissive 3-hydroxyisoquinolines by sequential Ugi-4CR-reductive Heck cyclization

What is it about?

A convergent approach to highly functionalized 3-hydroxyisoquinolines is reported. The key steps are an Ugi multicomponent reaction and a subsequent intramolecular reductive Heck reaction; these can also be performed as a one-pot procedure. The structures display very interesting properties as blue-fluorescence emitters.

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Why is it important?

Functional chromophores are rapidly accessible in a diversity-oriented fashion. Photophysical studies on the absorption and static fluorescence indicate that the substitution pattern on the pyridyl part influences the optical properties only to a minor extent, unless the amide substituent becomes sterically demanding and leads to significant nonradiative deactivation.