Stabilizing Fluorine–π Interactions

Li, Ping; Maier, Josef M.; Vik, Erik C.; Yehl, Christopher J.; Dial, Brent E.; Rickher, Amanda E.; Smith, Mark D.; Pellechia, Perry J.; Shimizu, Ken D.

doi:10.1002/ange.201702950

Cited by 23 publications

(17 citation statements)

References 60 publications

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“…This hypothesis seems aligned with fluorine substituent being capable of forming electrostatically driven and stabilizing F-p noncovalent interactions with aromatic molecular species, in donor:acceptor blends. 37,38 Alternatively, the slight different energy levels could also be playing a role. In particular, the LUMO of ITIC-4F is À4.07 eV, 39 compared to À3.92 eV for ITIC.…”

Section: Ast On As-cast Iticsmentioning

confidence: 99%

Structure dependent photostability of ITIC and ITIC-4F

et al. 2020

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Section: Ast On As-cast Iticsmentioning

confidence: 99%

Structure dependent photostability of ITIC and ITIC-4F

et al. 2020

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“…Thus, variations in the intramolecular interaction energies can be accurately measured via the folded−unfolded equilibrium. Our N-arylimide molecular balances have been successfully applied to a wide range of non-covalent interactions, including aromatic stacking, 18−21 heterocycle−π, 22 CH−π, 23−27 halogen−π, 28,29 chalcogen−π, 30 metal−π, 31 substituent−π, 32 and solvent effects. 33−37 For balances 1(CO)−6(CO), the carbonyl group of the N-pyridin-2(1H)-onyl rotor is held in close proximity in the folded conformer over the face of an aromatic shelf.…”

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confidence: 99%

Electrostatically Driven CO−π Aromatic Interactions

Vik

Maier

et al. 2019

J. Am. Chem. Soc.

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A series of N-arylimide molecular balances were developed to study and measure carbonyl–aromatic (CO−π) interactions. Carbonyl oxygens were observed to form repulsive interactions with unsubstituted arenes and attractive interactions with electron-deficient arenes with multiple electron-withdrawing groups. The repulsive and attractive CO−π aromatic interactions were well-correlated to electrostatic parameters, which allowed accurate predictions of the interaction energies based on the electrostatic potentials of the carbonyl and arene surfaces. Due to the pronounced electrostatic polarization of the CO bond, the CO−π aromatic interaction was stronger than the previously studied oxygen−π and halogen−π aromatic interactions.

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“…Recently, Shimizu et al. reported the results of their studies of fluorine⋅⋅⋅aromatic (F⋅⋅⋅π) interactions using N ‐arylimide molecular balances . In line with other studies, F⋅⋅⋅π interactions were stronger in the case of electron‐deficient aromatic rings.…”

Section: N‐arylimide Balancesmentioning

confidence: 64%

Some Recent Advances in the Design and Use of Molecular Balances for the Experimental Quantification of Intramolecular Noncovalent Interactions of π Systems

Aliev

Motherwell

2019

Chemistry A European J

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Herein, various molecular balances used for comparing the strengths of intramolecular noncovalent interactions are reviewed. Our overview indicates that considerable quantitative insight into the strength of noncovalent interactions can be gained through the careful design of molecular balances. Many exciting opportunities certainly exist for the design of further new balances to quantify and dissect the relative strengths of noncovalent interactions as a function of solvation and the importance of the many factors that contribute to overall molecular recognition. However, even simple model molecules can show a multiplicity of intramolecular noncovalent interactions acting in a combined fashion. It is therefore essential to undertake a detailed computational analysis to identify all possible noncovalent interactions present in a selected molecular balance prior to a quantitative experimental assessment of the strength of a particular noncovalent interaction. It is also argued that the words “torsion” and “molecular balance” seem to have become inextricably linked and, in consequence, even top pan and seesaw balances have been mistakenly referred to in these terms.

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Stabilizing Fluorine–π Interactions

Cited by 23 publications

References 60 publications

Structure dependent photostability of ITIC and ITIC-4F

Structure dependent photostability of ITIC and ITIC-4F

Electrostatically Driven CO−π Aromatic Interactions

Some Recent Advances in the Design and Use of Molecular Balances for the Experimental Quantification of Intramolecular Noncovalent Interactions of π Systems

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