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• W2317282989 endingPage "13691" @default.
• W2317282989 startingPage "13679" @default.
• W2317282989 abstract "The recent emergence of anion-π interactions has added a new dimension to supramolecular chemistry of anions. Yet, after a decade since its inception, actual mechanisms of anion-π interactions remain highly debated. To elicit a complete and accurate understanding of how different anions interact with π-electron-deficient 1,4,5,8-naphthalenediimides (NDIs) under different conditions, we have extensively studied these interactions using powerful experimental techniques. Herein, we demonstrate that, depending on the electron-donating abilities (Lewis basicity) of anions and electron-accepting abilities (π-acidity) of NDIs, modes of anion-NDI interactions vary from extremely weak non-chromogenic anion-π interactions to chromogenic anion-induced charge-transfer (CT) and electron-transfer (ET) phenomena. In aprotic solvents, electron-donating abilities of anions generally follow their Lewis basicity order, whereas π-acidity of NDIs can be fine-tuned by installing different electron-rich and electron-deficient substituents. While strongly Lewis basic anions (OH(-) and F(-)) undergo thermal ET with most NDIs, generating NDI(•-) radical anions and NDI(2-) dianions in aprotic solvents, weaker Lewis bases (AcO(-), H(2)PO(4)(-), Cl(-), etc.) often require the photoexcitation of moderately π-acidic NDIs to generate the corresponding NDI(•-) radical anions via photoinduced ET (PET). Poorly Lewis basic I(-) does not participate in thermal ET or PET with most NDIs (except with strongly π-acidic core-substituted dicyano-NDI) but forms anion/NDI CT or anion-π complexes. We have looked for experimental evidence that could indicate alternative mechanisms, such as a Meisenheimer complex or CH···anion hydrogen-bond formation, but none was found to support these possibilities." @default.
• W2317282989 created "2016-06-24" @default.
• W2317282989 creator A5011030691 @default.
• W2317282989 creator A5070609542 @default.
• W2317282989 creator A5072343066 @default.
• W2317282989 creator A5083157284 @default.
• W2317282989 date "2012-06-28" @default.
• W2317282989 modified "2023-10-05" @default.
• W2317282989 title "Boundaries of Anion/Naphthalenediimide Interactions: From Anion−π Interactions to Anion-Induced Charge-Transfer and Electron-Transfer Phenomena" @default.
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• W2317282989 doi "https://doi.org/10.1021/ja303173n" @default.
• W2317282989 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/22686833" @default.
• W2317282989 hasPublicationYear "2012" @default.
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