Progress in the synthesis of perylene bisimide dyes

• Published in: Organic chemistry frontiers an international journal of organic chemistry Vol. 6; no. 8; pp. 1272 - 1318
• Main Authors: Nowak-Król, Agnieszka, Würthner, Frank
• Format: Journal Article
• Language: English
• Published: London Royal Society of Chemistry 21.04.2019
• Subjects: Aromatic compounds; Carbonyl compounds; Carbonyl groups; Carbonyls; Chemical reactions; Dyes; Fluorescence; N-type semiconductors; Oligomers; Optical properties; Organic chemistry; Polycyclic aromatic hydrocarbons
• ISSN: 2052-4110; 2052-4110
• DOI: 10.1039/c8qo01368c

With their versatile absorption, fluorescence, n-type semiconducting and (photo-)stability properties, perylene bisimides have evolved as the most investigated compounds among polycyclic aromatic hydrocarbons during the last decade. In this review we collect the results from about 200 original publications, reporting a plethora of new perylene bisimide derivatives whose properties widely enrich the possibility for the application of these dyes beyond traditional fields. While some applications are highlighted, different from other recent reviews, our focus here is on the advances in the synthetic methodologies that have afforded new bay functionalizations, recently addressed functionalizations at the ortho-positions to the carbonyl groups, and annulation of carbo- and heterocyclic units. An impressive number of perylene bisimide oligomers are highlighted as well which are connected by single bonds or spiro linkage or in a fused manner, leading to arrays with fascinating optical and electronic properties.