Triplet carbene that is isolated as a solid and bottled for months

Abstract

AbstractOur efforts to isolate a triplet carbene as a solid so that one can “see” and keep it in a bottle have resulted in the most persistent species, namely, bis[10‐(4‐tert‐butyl‐2,6‐dimethylphenyl)‐9‐anthryl]carbene (31). This carbene was generated by photolysis of the corresponding diazo precursor (1‐N2) in toluene matrix at 77 K. The matrix was then warmed to −20°C in vacuo to evaporate the solvent to dryness, affording carbene 31 as a yellow solid. The isolated triplet carbene was shown to survive for several months at room temperature in a degassed and sealed tube.