A stable triplet diradical emitter

Molecules with luminescence have been extensively investigated, but the luminescence of a stable molecule with a triplet ground state has not been observed. Synthesis of boron-containing radicals has attracted lots of interest because of their unique electronic structures and potential applications in organic semiconductors. Though some boron-based diradicals have been reported, neutral boron-containing diradicals with triplet ground states are rare. Herein two borocyclic diradicals with different substituents ( 3 and 4 ) have been isolated. Their electronic structures were investigated by EPR and UV spectroscopy, and SQUID magnetometry, in conjunction with DFT calculations. Both experiment and calculation suggest that 3 is an open shell singlet diradical while 4 is a triplet ground state diradical with a large singlet-triplet gap (0.25 kcal mol −1 ). Both diradicals show multi fluorescence peaks ( 3 : 414, 431, and 470 nm; 4 : 420, 433, and 495 nm). 3 displays multiple redox steps and is a potential material towards the design of high-density memory devices. 4 represents the first example of a neutral triplet boron-containing diradical with a strong ferromagnetic interaction, and also is the first stable triplet diradical emitter. Stable borocyclic diradical emitters with a tunable ground state.