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Published on: March 10, 2023
Recent Advances in the Core-Annulation of Naphthalene Diimides
Alberto Insuasty1, Subashani Maniam2, Steven J Langford1
1Department of Chemistry and Biotechnology, Faculty of Science, Engineering & Technology, Swinburne University of Technology, Victoria, 3122, Australia.
Abstract:
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.
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