Standard

One-pot route to X-perfluoroarenes (X = Br, I) based on FeIII-assisted C-F functionalization and utilization of these arenes as building blocks for crystal engineering involving halogen bonding. / Rozhkov, Anton V.; Eliseeva, Anastasiya A.; Baykov, Sergey V.; Galmés, Bartomeu; Frontera, Antonio; Kukushkin, Vadim Yu.

In: Crystal Growth and Design, Vol. 20, No. 9, 02.09.2020, p. 5908-5921.

Research output: Contribution to journal › Article › peer-review

Harvard

Rozhkov, AV, Eliseeva, AA, Baykov, SV, Galmés, B, Frontera, A & Kukushkin, VY 2020, 'One-pot route to X-perfluoroarenes (X = Br, I) based on FeIII-assisted C-F functionalization and utilization of these arenes as building blocks for crystal engineering involving halogen bonding', Crystal Growth and Design, vol. 20, no. 9, pp. 5908-5921. https://doi.org/10.1021/acs.cgd.0c00606

APA

Rozhkov, A. V., Eliseeva, A. A., Baykov, S. V., Galmés, B., Frontera, A., & Kukushkin, V. Y. (2020). One-pot route to X-perfluoroarenes (X = Br, I) based on FeIII-assisted C-F functionalization and utilization of these arenes as building blocks for crystal engineering involving halogen bonding. Crystal Growth and Design, 20(9), 5908-5921. https://doi.org/10.1021/acs.cgd.0c00606

Vancouver

Rozhkov AV, Eliseeva AA, Baykov SV, Galmés B, Frontera A, Kukushkin VY. One-pot route to X-perfluoroarenes (X = Br, I) based on FeIII-assisted C-F functionalization and utilization of these arenes as building blocks for crystal engineering involving halogen bonding. Crystal Growth and Design. 2020 Sep 2;20(9):5908-5921. https://doi.org/10.1021/acs.cgd.0c00606

Author

Rozhkov, Anton V. ; Eliseeva, Anastasiya A. ; Baykov, Sergey V. ; Galmés, Bartomeu ; Frontera, Antonio ; Kukushkin, Vadim Yu. / One-pot route to X-perfluoroarenes (X = Br, I) based on FeIII-assisted C-F functionalization and utilization of these arenes as building blocks for crystal engineering involving halogen bonding. In: Crystal Growth and Design. 2020 ; Vol. 20, No. 9. pp. 5908-5921.

BibTeX

@article{fe598133962840fd990e849f3321822c,
title = "One-pot route to X-perfluoroarenes (X = Br, I) based on FeIII-assisted C-F functionalization and utilization of these arenes as building blocks for crystal engineering involving halogen bonding",
abstract = "Perfluorinated arenes (benzene(F) derivatives, diphenyl(F), naphthalene(F)) were converted into X-perfluoroarenes (X = Br, I) via the developed one-pot protocol based on [Fe(acetylacetonate)(3)]-assisted C-F functionalization. The syntheses proceed under mild conditions and employ readily available perfluorinated arenes, which are treated with EtMgBr followed by addition of X-2/[Fe(acetylacetonate)(3)] (0.8 mol %); yields range from good to moderate. The sigma-hole donor properties of the obtained mono-and di-X-perfluoroarenes and the significance of these species for halogen-bonding-based crystal engineering was illustrated in a series of postsynthetic experiments, all supported by density functional theory (DFT) energy calculations, molecular electrostatic potential (MEP) surface analysis, and the quantum theory of atoms in molecules (QTAIM). These include (i) a solid-state X-ray diffraction study of X-perfluoroarene self-association (dimerization) via iodine sigma-hole.electron belt interactions (three X-ray structures) and (ii) verification of X-perfluoroarene s-hole donor abilities by their interactions with iodides acting as external s-hole acceptors (five X-ray structures); a Hirshfeld surface analysis was performed for all eight structures.",
keywords = "NONCOVALENT INTERACTIONS, WEAK-INTERACTIONS, PI INTERACTIONS, COCRYSTALS, IODINE, CHALCOGEN, ENERGIES, STRATEGY, HYDROGEN, DIIODOACETYLENE",
author = "Rozhkov, {Anton V.} and Eliseeva, {Anastasiya A.} and Baykov, {Sergey V.} and Bartomeu Galm{\'e}s and Antonio Frontera and Kukushkin, {Vadim Yu}",
note = "Funding Information: The authors thank the Russian Science Foundation for support of these studies (project 20-13-00144). A.A.E. is grateful to Saint Petersburg State University for a postdoctoral fellowship. Physicochemical studies were performed at the Center for Magnetic Resonance, Center for X-ray Diffraction Studies, Center for Chemical Analysis and Materials Research, and Chemistry Educational Center (all belonging to Saint Petersburg State University). V.Y.K. is grateful to South Ural State University (Act 211 Government of the Russian Federation, contract No 02.A03.21.0011) for putting facilities at his disposal. A.F., who jointly with B.G. performed the theoretical calculations, thanks the MICIU/AEI (project CTQ2017-85821-R FEDER funds) for financial support. We are much obliged to Dr. O. Yu. Bakulina for valuable suggestions and experimental assistance. Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",
year = "2020",
month = sep,
day = "2",
doi = "10.1021/acs.cgd.0c00606",
language = "English",
volume = "20",
pages = "5908--5921",
journal = "Crystal Growth and Design",
issn = "1528-7483",
publisher = "American Chemical Society",
number = "9",

}

RIS

TY - JOUR

T1 - One-pot route to X-perfluoroarenes (X = Br, I) based on FeIII-assisted C-F functionalization and utilization of these arenes as building blocks for crystal engineering involving halogen bonding

AU - Rozhkov, Anton V.

AU - Eliseeva, Anastasiya A.

AU - Baykov, Sergey V.

AU - Galmés, Bartomeu

AU - Frontera, Antonio

AU - Kukushkin, Vadim Yu

N1 - Funding Information: The authors thank the Russian Science Foundation for support of these studies (project 20-13-00144). A.A.E. is grateful to Saint Petersburg State University for a postdoctoral fellowship. Physicochemical studies were performed at the Center for Magnetic Resonance, Center for X-ray Diffraction Studies, Center for Chemical Analysis and Materials Research, and Chemistry Educational Center (all belonging to Saint Petersburg State University). V.Y.K. is grateful to South Ural State University (Act 211 Government of the Russian Federation, contract No 02.A03.21.0011) for putting facilities at his disposal. A.F., who jointly with B.G. performed the theoretical calculations, thanks the MICIU/AEI (project CTQ2017-85821-R FEDER funds) for financial support. We are much obliged to Dr. O. Yu. Bakulina for valuable suggestions and experimental assistance. Publisher Copyright: Copyright © 2020 American Chemical Society. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

PY - 2020/9/2

Y1 - 2020/9/2

N2 - Perfluorinated arenes (benzene(F) derivatives, diphenyl(F), naphthalene(F)) were converted into X-perfluoroarenes (X = Br, I) via the developed one-pot protocol based on [Fe(acetylacetonate)(3)]-assisted C-F functionalization. The syntheses proceed under mild conditions and employ readily available perfluorinated arenes, which are treated with EtMgBr followed by addition of X-2/[Fe(acetylacetonate)(3)] (0.8 mol %); yields range from good to moderate. The sigma-hole donor properties of the obtained mono-and di-X-perfluoroarenes and the significance of these species for halogen-bonding-based crystal engineering was illustrated in a series of postsynthetic experiments, all supported by density functional theory (DFT) energy calculations, molecular electrostatic potential (MEP) surface analysis, and the quantum theory of atoms in molecules (QTAIM). These include (i) a solid-state X-ray diffraction study of X-perfluoroarene self-association (dimerization) via iodine sigma-hole.electron belt interactions (three X-ray structures) and (ii) verification of X-perfluoroarene s-hole donor abilities by their interactions with iodides acting as external s-hole acceptors (five X-ray structures); a Hirshfeld surface analysis was performed for all eight structures.

AB - Perfluorinated arenes (benzene(F) derivatives, diphenyl(F), naphthalene(F)) were converted into X-perfluoroarenes (X = Br, I) via the developed one-pot protocol based on [Fe(acetylacetonate)(3)]-assisted C-F functionalization. The syntheses proceed under mild conditions and employ readily available perfluorinated arenes, which are treated with EtMgBr followed by addition of X-2/[Fe(acetylacetonate)(3)] (0.8 mol %); yields range from good to moderate. The sigma-hole donor properties of the obtained mono-and di-X-perfluoroarenes and the significance of these species for halogen-bonding-based crystal engineering was illustrated in a series of postsynthetic experiments, all supported by density functional theory (DFT) energy calculations, molecular electrostatic potential (MEP) surface analysis, and the quantum theory of atoms in molecules (QTAIM). These include (i) a solid-state X-ray diffraction study of X-perfluoroarene self-association (dimerization) via iodine sigma-hole.electron belt interactions (three X-ray structures) and (ii) verification of X-perfluoroarene s-hole donor abilities by their interactions with iodides acting as external s-hole acceptors (five X-ray structures); a Hirshfeld surface analysis was performed for all eight structures.

KW - NONCOVALENT INTERACTIONS

KW - WEAK-INTERACTIONS

KW - PI INTERACTIONS

KW - COCRYSTALS

KW - IODINE

KW - CHALCOGEN

KW - ENERGIES

KW - STRATEGY

KW - HYDROGEN

KW - DIIODOACETYLENE

UR - http://www.scopus.com/inward/record.url?scp=85092071365&partnerID=8YFLogxK

U2 - 10.1021/acs.cgd.0c00606

DO - 10.1021/acs.cgd.0c00606

M3 - Article

AN - SCOPUS:85092071365

VL - 20

SP - 5908

EP - 5921

JO - Crystal Growth and Design

JF - Crystal Growth and Design

SN - 1528-7483

IS - 9

ER -

ID: 70661292