Investigations into the flow photochemical generation of triplet aryl cations, and the development of a practicable synthesis of electroluminescent ionic 2,2’-bifluorenes

Abstract

The development of an optimised experimental procedure for the synthesis of tetraimidazolium and tetrabenzimidazolium ionic 2,2’-bifluorenes is reported herein. Developed iteratively through several generations, it has improved the safety and reduced the waste associated with the ubiquitous method of preparing these and related electroluminescent compounds from the literature. This procedure has then been extended to diimidazolium species’, where an X-ray crystal structure has revealed how the triflate counterions can provide a second link between the alkylimidazolium residues and the photoluminescent core.
Additionally, building upon recent work within the Harrowven group, an investigation into the flow photochemical generation of triplet aryl cations from benzyl ortho-iodophenyl ethers has produced an array of functionalised benzochromenes, including new examples and the optimisation of some that have been previously reported. Several side reactions have been examined in detail, including the alternate formation of biaryl acetamides and fluorenes. The reaction has also been extended to the synthesis of encumbered biaryls by the inclusion of ortho and ortho’ substituents on the benzyl ring.

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Identifiers

ORCID for Edward Henry Jackman: orcid.org/0009-0001-5535-3829

ORCID for David Harrowven: orcid.org/0000-0001-6730-3573

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