Recent Advances in the Core‐Annulation of Naphthalene Diimides

• Published in: Chemistry : a European journal Vol. 25; no. 29; pp. 7058 - 7073
• Main Authors: Insuasty, Alberto, Maniam, Subashani, Langford, Steven J.
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 23.05.2019
• Subjects: annulation; annulenes; carbocycles; Charge transport; Chemical reactions; Chemistry; Coupling (molecular); Deoxyribonucleic acid; DNA; Electronic devices; Electronic equipment; Energy gap; heterocycles; Naphthalene; naphthalene diimides; Organic chemistry; Photovoltaics; Semiconductor devices; Transistors; Transport properties; aromatic compounds; core substitution; Naphthalene diimides; annulation; electron mobility
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201806009

This review focuses on describing all known synthetic strategies leading to core‐annulation of naphthalene diimides (NDIs). Strategies presented involve the formation of four‐, five‐ and six‐membered ring annulations bearing different heteroatomic and carbocyclic derivatives, including annulenes. The core‐annulation method opens the possibility for obtaining designer molecules with tuneable electronic characteristics such as a reduced energy band gap, and enhanced intermolecular overlap of π‐systems that improve electronic coupling between molecules—which is highly desirable for charge transport properties summarised in the final pages for applications in electronic devices such as organic field‐effect transistors (OFETs) and organic photovoltaic (OPV) cells. Molecular recognition in pH and fluoride sensing, or as a DNA probe, are some of additional applications of core‐annulated NDIs presented here. Additionally, recent advances in core modification of NDIs are presented, opening an entire new chemical avenue to be explored. Finally, the outlook on the future prospect of annulated NDIs in various applications is summarised. Ring round: With the growth in naphthalene diimides (NDIs) applicability in a broad range of fields, it is timely to review systematically the synthetic strategies used to make the diverse variety of core‐annulated systems. Strategies presented involve the formation of four‐, five‐ and six‐membered ring annulations bearing different heteroatomic and carbocyclic derivatives, including annulenes.