Kinetic Stabilization of Blue-Emissive Anthracenes: Phenylene Bridging Works Best

In attempts at kinetically stabilizing blue-emissive anthracenes, a series of 9,10-diaryl substituted derivatives were tested for their photochemical and photooxidative persistence. A major breakthrough in light fastness comes from a new bis-meta-terphenylyl substituted anthracene which is much superior to industrially relevant 9,10-biarylated anthracenes. The key issue is the steric shielding of the anthracene core. Further, intramolecular ring closure via Yamamoto coupling furnished a doubly bridged anthracene as a "self-encapsulated" sky-blue emitter which is most resistant to photodegradation. The improved stabilization was corroborated by time-resolved irradiation experiments and rationalized by X-ray crystallography.