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Recent Advances in the Core‐Annulation of Naphthalene Diimides
Author(s) -
Insuasty Alberto,
Maniam Subashani,
Langford Steven J.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201806009
Subject(s) - annulation , naphthalene , nanotechnology , band gap , intermolecular force , chemistry , molecule , combinatorial chemistry , materials science , optoelectronics , organic chemistry , catalysis
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.