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Synthesis of Functionalized Naphthalene Diimides and their Redox Properties
Author(s) -
Shukla Jyoti,
Mukhopadhyay Pritam
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901390
Subject(s) - chemistry , sonogashira coupling , stille reaction , redox , combinatorial chemistry , homo/lumo , ambipolar diffusion , electron donor , photochemistry , molecule , electron , organic chemistry , palladium , catalysis , physics , quantum mechanics
In this article, we have discussed the recently developed synthetic routes to amplify the electron‐poor nature of the naphthalenediimides (NDIs) as well as the integration of electron‐rich donor groups towards ambipolar and strongly electron donating NDIs. Non‐conventional electron withdrawing groups (EWGs) have been applied, leading to highly electron deficient NDIs. Highly π‐acidic molecules with LUMO levels up to –5.0 eV have now been realized. Cationic EWGs have been integrated at the NDI‐core resulting in six‐electron acceptors called “electron‐sponge”. Electron donating groups like tetrathiafulvalene, dicyanomethides, amino‐groups, etc. have been substituted to realize ambipolar NDIs with high HOMO levels and “electron‐reservoir” properties. Diverse coupling reactions such as, Suzuki, Sonogashira, Stille, Buchwald–Hartwig, etc. have been performed to achieve attractive redox properties. Double cross‐coupling reactions have been successful with metallacyclopentadienes to establish highly extended NDIs. The new synthetic routes to NDIs have significantly extended the electrochemical window, improved their optical properties and have resulted in attractive panchromatic systems and driven new applications.