Nitrile-substituted 2-(oxazolinyl)-phenols are efficient single-benzene, excited-state intramolecular proton transfer (ESPIT)-based fluorophores.

The direct hydroxylation of 2-aryloxazolines via a deprotonative magnesiation using TMPMgCl•LiCl and subsequent oxidation with molecular oxygen or air as a green oxidant is reported. This method proceeds under mild conditions at room temperature with high regioselectivity and chemoselectivity. The obtained phenols exhibit tunable luminescence properties, induced by excited-state intramolecular proton transfer. This method opens a new opportunity for the sustainable synthesis of luminescent organic molecules.

A highly regioselective functionalization of 7-bromofluorene-2-carbaldehydes, potent organic chromophores, in position C3 using a mild ortho-metallation strategy (DoM) with TMPMgCl·LiCl has been developed. This approach allows the preparation of highly functionalized fluorene derivatives by conversion of the in situ generated metalated species with various electrophiles giving a fast access to novel organic phosphorescent dyes.

Oxazolinyl- and arylchalcogenazolyl-substituted hydroxyfluorenes exhibiting excited-state intramolecular proton transfer (ESIPT) are described as potent and highly modular luminophores.

Minimalistic 2-(oxazolinyl)-phenols substituted with different electron-donating and -withdrawing groups as well as 1,2,5chalcogenadiazole-annulated derivatives thereof were synthesized and investigated in regard to their emission behavior in solution as well as in the solid state. Depending on the nature of the incorporated substituent and its position, emission efficiencies were increased or diminished, resulting in AIE or ACQ characteristics. Single-crystal analysis revealed J-and H-type packing motifs and a so-far undescribed isolation of ESIPT-based fluorophores in the keto form.