skip to main content
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Understanding Polyarene Trifluoromethylation with Hot CF 3 Radicals Using Corannulene: Understanding Polyarene Trifluoromethylation with Hot CF 3 Radicals Using Corannulene

Authors:
ORCiD logo [1];  [1]; ORCiD logo [2]; ORCiD logo [3]; ORCiD logo [2]; ORCiD logo [1]; ORCiD logo [4]; ORCiD logo [1]
  1. Department of Chemistry, Colorado State University, 80523 Fort Collins CO USA
  2. Department of Chemistry, University at Albany, State University of New York, 12222 Albany NY USA
  3. ChemMatCARS, University of Chicago Advanced Photon Source, 60439 Argonne IL USA
  4. Liebniz Institute for Solid State and Materials Research, D01069 Dresden Germany
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1461010
Grant/Contract Number:  
AC02-06CH11357
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
European Journal of Organic Chemistry
Additional Journal Information:
Journal Name: European Journal of Organic Chemistry Journal Volume: 2018 Journal Issue: 31; Journal ID: ISSN 1434-193X
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
Germany
Language:
English

Citation Formats

Kuvychko, Igor V., Clikeman, Tyler, Dubceac, Cristina, Chen, Yu-Sheng, Petrukhina, Marina A., Strauss, Steven H., Popov, Alexey A., and Boltalina, Olga V. Understanding Polyarene Trifluoromethylation with Hot CF 3 Radicals Using Corannulene: Understanding Polyarene Trifluoromethylation with Hot CF 3 Radicals Using Corannulene. Germany: N. p., 2018. Web. doi:10.1002/ejoc.201800508.
Kuvychko, Igor V., Clikeman, Tyler, Dubceac, Cristina, Chen, Yu-Sheng, Petrukhina, Marina A., Strauss, Steven H., Popov, Alexey A., & Boltalina, Olga V. Understanding Polyarene Trifluoromethylation with Hot CF 3 Radicals Using Corannulene: Understanding Polyarene Trifluoromethylation with Hot CF 3 Radicals Using Corannulene. Germany. doi:https://doi.org/10.1002/ejoc.201800508
Kuvychko, Igor V., Clikeman, Tyler, Dubceac, Cristina, Chen, Yu-Sheng, Petrukhina, Marina A., Strauss, Steven H., Popov, Alexey A., and Boltalina, Olga V. Thu . "Understanding Polyarene Trifluoromethylation with Hot CF 3 Radicals Using Corannulene: Understanding Polyarene Trifluoromethylation with Hot CF 3 Radicals Using Corannulene". Germany. doi:https://doi.org/10.1002/ejoc.201800508.
@article{osti_1461010,
title = {Understanding Polyarene Trifluoromethylation with Hot CF 3 Radicals Using Corannulene: Understanding Polyarene Trifluoromethylation with Hot CF 3 Radicals Using Corannulene},
author = {Kuvychko, Igor V. and Clikeman, Tyler and Dubceac, Cristina and Chen, Yu-Sheng and Petrukhina, Marina A. and Strauss, Steven H. and Popov, Alexey A. and Boltalina, Olga V.},
abstractNote = {},
doi = {10.1002/ejoc.201800508},
journal = {European Journal of Organic Chemistry},
number = 31,
volume = 2018,
place = {Germany},
year = {2018},
month = {7}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: https://doi.org/10.1002/ejoc.201800508

Citation Metrics:
Cited by: 4 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Taming Hot CF 3 Radicals: Incrementally Tuned Families of Polyarene Electron Acceptors for Air-Stable Molecular Optoelectronics
journal, March 2013

  • Kuvychko, Igor V.; Castro, Karlee P.; Deng, S. H. M.
  • Angewandte Chemie International Edition, Vol. 52, Issue 18
  • DOI: 10.1002/anie.201300085

A Buckybowl with a Lot of Potential: C5-C20H5(CF3)5
journal, April 2012

  • Kuvychko, Igor V.; Spisak, Sarah N.; Chen, Yu-Sheng
  • Angewandte Chemie International Edition, Vol. 51, Issue 20
  • DOI: 10.1002/anie.201200178

Molecular Packing and Symmetry of Two-Dimensional Crystals
journal, April 2007

  • Plass, Katherine E.; Grzesiak, Adam L.; Matzger, Adam J.
  • Accounts of Chemical Research, Vol. 40, Issue 4
  • DOI: 10.1021/ar0500158

Strategien für die Synthese funktioneller Naphthalindiimide
journal, June 2014


Dürer–Kepler–Penrose, the development of pentagon tilings
journal, December 2000


Die “Renaissance” der radikalischen Trifluormethylierung
journal, August 2012


Fluorinated and Trifluoromethylated Corannulenes
journal, September 2013

  • Schmidt , Bernd M.; Topolinski , Berit; Yamada , Mihoko
  • Chemistry - A European Journal, Vol. 19, Issue 41
  • DOI: 10.1002/chem.201301910

Synthesis of perfluoroalkylated pentacenes and evaluation of their fundamental physical properties
journal, January 2017

  • Yamada, Shigeyuki; Kinoshita, Keita; Iwama, Shota
  • Organic & Biomolecular Chemistry, Vol. 15, Issue 12
  • DOI: 10.1039/C7OB00043J

Incremental Tuning Up of Fluorous Phenazine Acceptors
journal, January 2016

  • Castro, Karlee P.; Clikeman, Tyler T.; DeWeerd, Nicholas J.
  • Chemistry - A European Journal, Vol. 22, Issue 12
  • DOI: 10.1002/chem.201504122

Analysis of the NMR through-space coupling mechanism between 19F atoms
journal, August 2004


Surface-Supported Supramolecular Pentamers
journal, September 2013

  • Karan, Sujoy; Wang, Yongfeng; Robles, Roberto
  • Journal of the American Chemical Society, Vol. 135, Issue 38
  • DOI: 10.1021/ja405456k

The role of fivefold symmetry in suppressing crystallization
journal, October 2016

  • Taffs, Jade; Patrick Royall, C.
  • Nature Communications, Vol. 7, Issue 1
  • DOI: 10.1038/ncomms13225

C 20 H 4 (C 4 F 8 ) 3 : A Fluorine-Containing Annulated Corannulene that Is a Better Electron Acceptor Than C 60
journal, June 2013

  • Kuvychko, Igor V.; Dubceac, Cristina; Deng, Shihu H. M.
  • Angewandte Chemie International Edition, Vol. 52, Issue 29
  • DOI: 10.1002/anie.201300796

Gear-Meshed Tiling of Surfaces with Molecular Pentagonal Stars
journal, January 2014

  • Stöckl, Quirin; Bandera, Davide; Kaplan, Craig S.
  • Journal of the American Chemical Society, Vol. 136, Issue 2
  • DOI: 10.1021/ja411279r

High-Mobility Air-Stable n-Type Semiconductors with Processing Versatility: Dicyanoperylene-3,4:9,10-bis(dicarboximides)
journal, November 2004

  • Jones, Brooks A.; Ahrens, Michael J.; Yoon, Myung-Han
  • Angewandte Chemie International Edition, Vol. 43, Issue 46
  • DOI: 10.1002/anie.200461324

Pentagonal tiling with buckybowls: pentamethylcorannulene on Cu(111)
journal, January 2012

  • Zoppi, Laura; Bauert, Tobias; Siegel, Jay S.
  • Physical Chemistry Chemical Physics, Vol. 14, Issue 38
  • DOI: 10.1039/c2cp41732d

Halogenation of a Nonplanar Molecular Semiconductor to Tune Energy Levels and Bandgaps for Electron Transport
journal, February 2015


Strategies for the Synthesis of Functional Naphthalene Diimides
journal, June 2014

  • Suraru, Sabin-Lucian; Würthner, Frank
  • Angewandte Chemie International Edition, Vol. 53, Issue 29
  • DOI: 10.1002/anie.201309746

Corannulene. A Three-Step Synthesis 1
journal, November 1997

  • Scott, Lawrence T.; Cheng, Pei-Chao; Hashemi, Mohammed M.
  • Journal of the American Chemical Society, Vol. 119, Issue 45
  • DOI: 10.1021/ja972019g

A “Renaissance” in Radical Trifluoromethylation
journal, August 2012


Core Perylene Diimide Designs via Direct Bay- and ortho -(Poly)trifluoromethylation: Synthesis, Isolation, X-ray Structures, Optical and Electronic Properties : Core Perylene Diimide Designs
journal, September 2015

  • Clikeman, Tyler T.; Bukovsky, Eric V.; Wang, Xue-Bin
  • European Journal of Organic Chemistry, Vol. 2015, Issue 30
  • DOI: 10.1002/ejoc.201501024

A Buckybowl with a Lot of Potential: C5-C20H5(CF3)5
journal, April 2012

  • Kuvychko, Igor V.; Spisak, Sarah N.; Chen, Yu-Sheng
  • Angewandte Chemie, Vol. 124, Issue 20
  • DOI: 10.1002/ange.201200178

Observation of multiple dielectric relaxations in BaTiO3-Bi(Li1/3Ti2/3)O3 ceramics
journal, October 2017


Poly(trifluoromethyl)azulenes: structures and acceptor properties
journal, January 2014

  • Clikeman, Tyler T.; Bukovsky, Eric V.; Kuvychko, Igor V.
  • Chem. Commun., Vol. 50, Issue 47
  • DOI: 10.1039/C4CC00510D

Taming Hot CF 3 Radicals: Incrementally Tuned Families of Polyarene Electron Acceptors for Air-Stable Molecular Optoelectronics
journal, March 2013

  • Kuvychko, Igor V.; Castro, Karlee P.; Deng, S. H. M.
  • Angewandte Chemie, Vol. 125, Issue 18
  • DOI: 10.1002/ange.201300085

Perfluoroalkylation of Aromatic Compounds
journal, October 1960

  • Tiers, George V. D.
  • Journal of the American Chemical Society, Vol. 82, Issue 20
  • DOI: 10.1021/ja01505a059

Kilogram-Scale Production of Corannulene
journal, March 2012

  • Butterfield, Anna M.; Gilomen, Bruno; Siegel, Jay S.
  • Organic Process Research & Development, Vol. 16, Issue 4
  • DOI: 10.1021/op200387s

Erecting buckybowls onto their edge: 2D self-assembly of terphenylcorannulene on the Cu(111) surface
journal, January 2017

  • Stöckl, Quirin S.; Wu, Tsun-Cheng; Mairena, Anaïs
  • Faraday Discussions, Vol. 204
  • DOI: 10.1039/C7FD00109F

Novel laser crystals in Ca9Y(VO4)7-x(PO4)x mixed system
journal, June 2017


C 20 H 4 (C 4 F 8 ) 3 : A Fluorine-Containing Annulated Corannulene that Is a Better Electron Acceptor Than C 60
journal, June 2013

  • Kuvychko, Igor V.; Dubceac, Cristina; Deng, Shihu H. M.
  • Angewandte Chemie, Vol. 125, Issue 29
  • DOI: 10.1002/ange.201300796

Perfluoroalkylfullerenes
journal, August 2014

  • Boltalina, Olga V.; Popov, Alexey A.; Kuvychko, Igor V.
  • Chemical Reviews, Vol. 115, Issue 2
  • DOI: 10.1021/cr5002595

Syntheses and Properties of Buckybowls Bearing Electron-withdrawing Groups
journal, February 2014

  • Schmidt, Bernd M.; Lentz, Dieter
  • Chemistry Letters, Vol. 43, Issue 2
  • DOI: 10.1246/cl.130984

High-Mobility Air-Stable n-Type Semiconductors with Processing Versatility: Dicyanoperylene-3,4:9,10-bis(dicarboximides)
journal, November 2004

  • Jones, Brooks A.; Ahrens, Michael J.; Yoon, Myung-Han
  • Angewandte Chemie, Vol. 116, Issue 46
  • DOI: 10.1002/ange.200461324