Kinetic Stabilization of Blue‐Emissive Anthracenes: Phenylene Bridging Works Best. Issue 67 (12th October 2021)

• Record Type: Journal Article
• Authors: Nathusius, Marvin; Sleeman, Daniel; Pan, Junyou; Rominger, Frank; Freudenberg, Jan; Bunz, Uwe H. F.; Müllen, Klaus
• Is Part Of: Chemistry. Volume 27:Issue 67(2021)
• Page Start: 16606
• Page End: 16610
• Publication Date: 2021-10-12
• Subjects: anthracene -- organic materials -- photostability -- stabilization -- x-ray diffraction; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202103285
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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. Abstract : In attempts at kinetically stabilizing blue‐emissive anthracenes a series of 9, 10‐biarylated derivatives were investigated. Bis‐ meta ‐terphenylyl substitution highly increased photochemical and photooxidative stability. Ring closure to [6]cyclo‐ meta ‐hexaphenylene bridged anthracene increased protection even further resulting in an additional stabilization.