Photolysis at 386 nm produces the lowest triplet excited state of a thioxanthone (TX) that undergoes exothermic energy transfer (et) to the linked naphthothiophene-2-carboxamide anilide, which results in electrocyclization and efficient leaving group (LG<sup>-</sup>) expulsion via a putative zwitterionic intermediate. Quantum yields are comparable to the intermolecular sensitized reaction. Direct coupling of the TX to the 2-carboxamide nitrogen gives less efficient electrocyclization between benzo group of TX and thiophene ring and is thought to involve a less efficient energy transfer step.

Photochemical expulsion of leaving groups from a naphthothiophene-2-carboxamide anilide linked to a chromophore by a flexible polymethylene chain

254th National Meeting (2017)

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