Direct Evidence of Visible Light-Induced Homolysis in Chlorobis(2,9-dimethyl-1,10-phenanthroline)copper(II)

Fayad, Remi; Engl, Sebastian; Danilov, Evgeny O.; Hauke, Cory E.; Reiser, Oliver; Castellano, Felix N.

doi:10.1021/acs.jpclett.0c01601

Title: Direct Evidence of Visible Light-Induced Homolysis in Chlorobis(2,9-dimethyl-1,10-phenanthroline)copper(II)

Abstract

Developments in the field of photoredox catalysis that leveraged the long-lived excited states of Ir(III) and Ru(II) photosensi-tizers to enable radical coupling processes, paved the way for explorations of synthetic transformations that would otherwise remain unrealized. While first row transition metal photocatalysts have not been as extensively investigated, valuable syn-thetic transformations covering broad scopes of olefin functionalization have been recently reported featuring photoactivated chlorobis(phenanthroline) Cu(II) complexes. In the current study, the photochemical processes underpinning the catalytic activity of [Cu(dmp)2Cl]Cl (dmp = 2,9-dimethyl-1,10-phenanthroline) were investigated. The combined results from static spectroscopic investigations and conventional photochemistry, ultrafast transient absorption, and electron paramagnetic reso-nance (EPR) spin trapping experiments, strongly support blue light (λex = 427 or 470 nm) induced Cu-Cl homolytic bond cleavage in [Cu(dmp)2Cl]+ occurring in less than 100 femtoseconds. Based on electronic structure calculations, this bond breaking photochemistry corresponds to the Cl → Cu(II) ligand-to-metal charge transfer (LMCT) transition, unmasking a Cu(I) species [Cu(dmp)2]+ and a Cl• atom, thereby serving as a departure point for both Cu(I)- or Cu(II)-based photoredox transformations. No net photochemistry was observed through direct excitation of the ligand-field transitions in the red (λex = 785 or 800 nm), and all combined experiments indicated no evidence of Cu-Clmore »« less

Authors:

Fayad, Remi ^[1]; Engl, Sebastian ^[2];

^[1];

^[2];

^[1]

North Carolina State Univ., Raleigh, NC (United States)
Univ. of Regensburg (Germany)

Publication Date:: Mon Jun 15 00:00:00 EDT 2020

Research Org.:: Princeton Univ., NJ (United States); North Carolina State University, Raleigh, NC (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

OSTI Identifier:: 1634193

Alternate Identifier(s):: OSTI ID: 1643989

Grant/Contract Number:: SC0019370; SC0011979

Resource Type:: Accepted Manuscript

Journal Name:: Journal of Physical Chemistry Letters

Additional Journal Information:: Journal Volume: 11; Journal ID: ISSN 1948-7185

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; redox reactions; adducts; absorption; electron paramagnetic resonance spectroscopy; excited states

Citation Formats


                    Fayad, Remi, Engl, Sebastian, Danilov, Evgeny O., Hauke, Cory E., Reiser, Oliver, and Castellano, Felix N. Direct Evidence of Visible Light-Induced Homolysis in Chlorobis(2,9-dimethyl-1,10-phenanthroline)copper(II).  United States: N. p., 2020. 
Web.  doi:10.1021/acs.jpclett.0c01601.

Copy to clipboard


                    Fayad, Remi, Engl, Sebastian, Danilov, Evgeny O., Hauke, Cory E., Reiser, Oliver, & Castellano, Felix N. Direct Evidence of Visible Light-Induced Homolysis in Chlorobis(2,9-dimethyl-1,10-phenanthroline)copper(II).  United States.  https://doi.org/10.1021/acs.jpclett.0c01601

Copy to clipboard


                    Fayad, Remi, Engl, Sebastian, Danilov, Evgeny O., Hauke, Cory E., Reiser, Oliver, and Castellano, Felix N. Mon .  
"Direct Evidence of Visible Light-Induced Homolysis in Chlorobis(2,9-dimethyl-1,10-phenanthroline)copper(II)".  United States.  https://doi.org/10.1021/acs.jpclett.0c01601.  https://www.osti.gov/servlets/purl/1634193.

Copy to clipboard


                    
@article{osti_1634193,

  title        = {Direct Evidence of Visible Light-Induced Homolysis in Chlorobis(2,9-dimethyl-1,10-phenanthroline)copper(II)},

  author       = {Fayad, Remi and Engl, Sebastian and Danilov, Evgeny O. and Hauke, Cory E. and Reiser, Oliver and Castellano, Felix N.},

  abstractNote = {Developments in the field of photoredox catalysis that leveraged the long-lived excited states of Ir(III) and Ru(II) photosensi-tizers to enable radical coupling processes, paved the way for explorations of synthetic transformations that would otherwise remain unrealized. While first row transition metal photocatalysts have not been as extensively investigated, valuable syn-thetic transformations covering broad scopes of olefin functionalization have been recently reported featuring photoactivated chlorobis(phenanthroline) Cu(II) complexes. In the current study, the photochemical processes underpinning the catalytic activity of [Cu(dmp)2Cl]Cl (dmp = 2,9-dimethyl-1,10-phenanthroline) were investigated. The combined results from static spectroscopic investigations and conventional photochemistry, ultrafast transient absorption, and electron paramagnetic reso-nance (EPR) spin trapping experiments, strongly support blue light (λex = 427 or 470 nm) induced Cu-Cl homolytic bond cleavage in [Cu(dmp)2Cl]+ occurring in less than 100 femtoseconds. Based on electronic structure calculations, this bond breaking photochemistry corresponds to the Cl → Cu(II) ligand-to-metal charge transfer (LMCT) transition, unmasking a Cu(I) species [Cu(dmp)2]+ and a Cl• atom, thereby serving as a departure point for both Cu(I)- or Cu(II)-based photoredox transformations. No net photochemistry was observed through direct excitation of the ligand-field transitions in the red (λex = 785 or 800 nm), and all combined experiments indicated no evidence of Cu-Cl bond cleavage under these conditions. The underlying visible light-induced homolysis (VLIH) of a metal-ligand bond yielding a one electron reduced photosensitizer and a radical species, may form the basis for novel transformations initiated by photoinduced homolysis featuring in-situ formed metal-substrate adducts utilizing first row transition metal complexes.},

  doi          = {10.1021/acs.jpclett.0c01601},

  journal      = {Journal of Physical Chemistry Letters},

  number       = ,

  volume       = 11,

  place        = {United States},

  year         = {Mon Jun 15 00:00:00 EDT 2020},

  month        = {Mon Jun 15 00:00:00 EDT 2020}

}

Copy to clipboard

Journal Article:

Free Publicly Available Full Text

Accepted Manuscript (DOE)

Publisher's Version of Record

https://doi.org/10.1021/acs.jpclett.0c01601

Other availability

Search WorldCat to find libraries that may hold this journal

Citation Metrics:

Cited by: 30 works

Citation information provided by
Web of Science

Save / Share:

Export Metadata

Save to My Library

Works referenced in this record:

Visible-Light Photocatalysis: Does It Make a Difference in Organic Synthesis?
journal, June 2018

Marzo, Leyre; Pagire, Santosh K.; Reiser, Oliver
Angewandte Chemie International Edition, Vol. 57, Issue 32
DOI: 10.1002/anie.201709766

Photoredox Catalysis in Organic Chemistry
journal, June 2016

Shaw, Megan H.; Twilton, Jack; MacMillan, David W. C.
The Journal of Organic Chemistry, Vol. 81, Issue 16
DOI: 10.1021/acs.joc.6b01449

Recent progress in the development of transition-metal based photoredox catalysts
journal, February 2020

Glaser, Felix; Wenger, Oliver S.
Coordination Chemistry Reviews, Vol. 405
DOI: 10.1016/j.ccr.2019.213129

Copper’s rapid ascent in visible-light photoredox catalysis
journal, May 2019

Hossain, Asik; Bhattacharyya, Aditya; Reiser, Oliver
Science, Vol. 364, Issue 6439
DOI: 10.1126/science.aav9713

Heteroleptic Copper(I)-Based Complexes for Photocatalysis: Combinatorial Assembly, Discovery, and Optimization
journal, April 2018

Minozzi, Clémentine; Caron, Antoine; Grenier-Petel, Jean-Christophe
Angewandte Chemie International Edition, Vol. 57, Issue 19
DOI: 10.1002/anie.201800144

Transient Absorption Dynamics of Sterically Congested Cu(I) MLCT Excited States
journal, March 2015

Garakyaraghi, Sofia; Danilov, Evgeny O.; McCusker, Catherine E.
The Journal of Physical Chemistry A, Vol. 119, Issue 13
DOI: 10.1021/acs.jpca.5b00901

Design of a Long-Lifetime, Earth-Abundant, Aqueous Compatible Cu(I) Photosensitizer Using Cooperative Steric Effects
journal, July 2013

McCusker, Catherine E.; Castellano, Felix N.
Inorganic Chemistry, Vol. 52, Issue 14
DOI: 10.1021/ic401213p

Making Copper Photocatalysis Even More Robust and Economic: Photoredox Catalysis with [Cu ^II (dmp) ₂ Cl]Cl: Making Copper Photocatalysis Even More Robust and Economic: Photoredox Catalysis with [Cu ^II (dmp) ₂ Cl]Cl
journal, July 2019

Engl, Sebastian; Reiser, Oliver
European Journal of Organic Chemistry, Vol. 2020, Issue 10
DOI: 10.1002/ejoc.201900839

Visible‐Light‐Accelerated Copper(II)‐Catalyzed Regio‐ and Chemoselective Oxo‐Azidation of Vinyl Arenes
journal, July 2018

Hossain, Asik; Vidyasagar, Adiyala; Eichinger, Christian
Angewandte Chemie International Edition, Vol. 57, Issue 27
DOI: 10.1002/anie.201801678

Photolyses of Metal Compounds: Cupric Chloride in Organic Media
journal, June 1962

Kochi, Jay K.
Journal of the American Chemical Society, Vol. 84, Issue 11
DOI: 10.1021/ja00870a025

³ d-d Excited States of Ni(II) Complexes Relevant to Photoredox Catalysis: Spectroscopic Identification and Mechanistic Implications
journal, March 2020

Ting, Stephen I.; Garakyaraghi, Sofia; Taliaferro, Chelsea M.
Journal of the American Chemical Society, Vol. 142, Issue 12
DOI: 10.1021/jacs.0c00781

Exploring Chromium(III)−Alkyl Bond Homolysis with CpCr[(ArNCMe) ₂ CH](R) Complexes
journal, December 2010

MacLeod, K. Cory; Conway, Julia L.; Patrick, Brian O.
Journal of the American Chemical Society, Vol. 132, Issue 48
DOI: 10.1021/ja1083392

Photoredox behaviour of chlorocopper(II) complexes in acetonitrile: mechanism and quantum yields
journal, January 1979

Cervone, E.; Diomedi Camassei, F.; Giannini, I.
Journal of Photochemistry, Vol. 11, Issue 5
DOI: 10.1016/0047-2670(79)85021-2

Photochemistry of copper(II) chlorocomplexes in acetonitrile: Trapping the ligand-to-metal charge transfer excited state relaxations pathways
journal, November 2014

Mereshchenko, Andrey S.; Olshin, Pavel K.; Karimov, Artur M.
Chemical Physics Letters, Vol. 615
DOI: 10.1016/j.cplett.2014.10.016

Electron spin resonance of .beta.-chloroalkyl nitroxides. Angular dependence of .beta.-chlorine hyperfine coupling
journal, July 1970

Janzen, Edward G.; Knauer, Bruce R.; Williams, Lewis T.
The Journal of Physical Chemistry, Vol. 74, Issue 15
DOI: 10.1021/j100709a033

On the spin trapping of chlorine atoms. Competition from chloride ions
journal, July 1991

Rehorek, Detlef; Janzen, Edward G.; Kotake, Yashige
Canadian Journal of Chemistry, Vol. 69, Issue 7
DOI: 10.1139/v91-167

Ultrafast Structural Rearrangements in the MLCT Excited State for Copper(I) bis- Phenanthrolines in Solution
journal, February 2007

Shaw, George B.; Grant, Christian D.; Shirota, Hideaki
Journal of the American Chemical Society, Vol. 129, Issue 7
DOI: 10.1021/ja067271f

Electronic structures of ion radicals of nitrogen-heteroaromatic hydrocarbons as studied by ESR and optical spectroscopy
journal, November 1979

Kato, Tatsuhisa; Shida, Tadamasa
Journal of the American Chemical Society, Vol. 101, Issue 23
DOI: 10.1021/ja00517a014

Trap-Free Halogen Photoelimination from Mononuclear Ni(III) Complexes
journal, May 2015

Hwang, Seung Jun; Powers, David C.; Maher, Andrew G.
Journal of the American Chemical Society, Vol. 137, Issue 20
DOI: 10.1021/jacs.5b03192

Ultraviolet/visible spectra of halogen molecule/arene and halogen atom/arene .pi.-molecular complexes
journal, January 1989

Raner, K. D.; Lusztyk, J.; Ingold, K. U.
The Journal of Physical Chemistry, Vol. 93, Issue 2
DOI: 10.1021/j100339a016

Transient Charge-transfer Complexes with Chlorine Atoms by Pulse Radiolysis of Carbon Tetrachloride Solutions
journal, June 1967

BÜHler, R. E.; Ebert, M.
Nature, Vol. 214, Issue 5094
DOI: 10.1038/2141220a0

Selective functionalization of methane, ethane, and higher alkanes by cerium photocatalysis
journal, July 2018

Hu, Anhua; Guo, Jing-Jing; Pan, Hui
Science, Vol. 361, Issue 6403
DOI: 10.1126/science.aat9750

Ligand-Accelerated Iron Photocatalysis Enabling Decarboxylative Alkylation of Heteroarenes
journal, May 2019

Li, Zhenlong; Wang, Xiaofei; Xia, Siqi
Organic Letters, Vol. 21, Issue 11
DOI: 10.1021/acs.orglett.9b01439

Similar Records in DOE PAGES and OSTI.GOV collections:

³d-d Excited States of Ni(II) Complexes Relevant to Photoredox Catalysis: Spectroscopic Identification and Mechanistic Implications

Journal Article Ting, Stephen I. ; Garakyaraghi, Sofia ; Taliaferro, Chelsea M. ; ... - Journal of the American Chemical Society

Synthetic organic chemistry has seen major advances due to the merger of nickel and photoredox catalysis. A growing number of Ni-photoredox reactions are proposed to involve generation of excited nickel species, sometimes even in the absence of a photoredox catalyst. To gain insights about these excited states, two of our groups previously studied the photophysics of Ni(^t-Bubpy)(o-Tol)Cl, which is representative of proposed intermediates in many Ni-photoredox reactions. This complex was found to have a long-lived excited state (τ = 4 ns), which was computationally assigned as a metal-to-ligand charge transfer (MLCT) state with an energy of 1.6 eV (38 kcal/mol).more »« less
Cited by 103
https://doi.org/10.1021/jacs.0c00781

Full Text Available
Improvement of the photochemical reactivity of (Cu(dmp)P2) (dmp = 2,9-dimethyl-1,10-phenanthroline; P = tertiary phosphine) by substituting PPh3 with larger phosphines: application to photoreduction of methylviologen

Journal Article Sakaki, S ; Koga, G ; Hinokuma, S ; ... - Inorg. Chem.; (United States)

Cu(I) complexes containing heteroaromatic ligands such as 2,2'-bipyridine (bpy) or 1,10-phenanthroline exhibit a metal-to-ligand charge-transfer (MLCT) band in the visible to near-ultraviolet spectral region and have a triplet MLCT state as the lowest energy excited state like (Ru(bpy)3)S which has been applied extensively to the photochemical reduction of water to hydrogen gas. Nevertheless, application of those Cu(I) complexes to the photochemical reduction of water has not been carried out, excepting only one report of Sauvage et al. Recently, they reported that Cu(I) complexes containing a heteroaromatic ligand, (Cu(NN)(PPh3)2) (NN = 2,9-dimethyl-1,10-phenanthroline (dmp) or 4,4',6,6'-tetramethyl-2,2'-bipyridine), found application as a sensitizer inmore »« less
https://doi.org/10.1021/ic00258a036
Synthetic and Mechanistic Implications of Chlorine Photoelimination in Nickel/Photoredox C(sp³)–H Cross-Coupling

Journal Article Kariofillis, Stavros K. ; Doyle, Abigail G. - Accounts of Chemical Research

In recent years, the development of light-driven reactions has contributed numerous advances in synthetic organic chemistry. A particularly active research area combines photoredox catalysis with nickel catalysis to accomplish otherwise inaccessible cross-coupling reactions. In these reactions, the photoredox catalyst absorbs light to generate an electronically excited charge-transfer state that can engage in electron or energy transfer with a substrate and the nickel catalyst. Our group questioned whether photoinduced activation of the nickel catalyst itself could also contribute new approaches to cross-coupling. Over the past five years, we have sought to advance this hypothesis for the development of a suite ofmore »« less
https://doi.org/10.1021/acs.accounts.0c00694

Full Text Available
Intriguing Effects of Halogen Substitution on the Photophysical Properties of 2,9-(Bis)halo-Substituted Phenanthrolinecopper(I) Complexes

Journal Article Brown-Xu, Samantha ; Fumanal, Maria ; Gourlaouen, Christophe ; ... - Inorganic Chemistry

Three new copper(I) complexes [Cu-(L-x)(2)](+)(PF6-) (where L-x stands for 2,9-dihalo-1,10-phenanthroline and X = Cl, Br, and I) have been synthesized in order to study the impact of halogen substituents tethered in the alpha position of the chelating nitrogen atoms on their physical properties. The photophysical properties of these new complexes (hereafter named Cu-X) were characterized in both their ground and excited states. Femtosecond ultrafast spectroscopy revealed that early photoinduced processes are faster for Cu-I than for Cu-Cl or Cu-Br, both showing similar behaviors. Their electronic absorption and electrochemical properties are comparable to benchmark [Cu(dmp)(2)](+) (where dmp stands for 2,9-dimethyl-1,10-phenanthroline); furthermore,more »« less
https://doi.org/10.1021/acs.inorgchem.9b00042
Mechanism of action of the copper(I) complex of 2,9-dimethyl-1,10-phenanthroline on Mycoplasma gallisepticum

Journal Article Smit, H ; van der Goot, H ; Nauta, W T ; ... - Antimicrob. Agents Chemother.; (United States)

Evidence was found that the inhibitory action of Cu(DMP)/sub 2/NO/sub 3/, the copper(I) complex of 2,9-dimethyl-1,10-phenanthroline (DMP), on Mycoplasma gallisepticum is a consequence of the ultimate toxicity of copper, and not that of the ligand, DMP. From uptake studies with radiolabeled /sup 67/Cu and (/sup 14/C)DMP, we concluded that significantly more copper than DMP is bound to the mycoplasmal cell. It appeared that dissociation of Cu(DMP)2+ occurred shortly after interaction with the cell membrane. Copper was transported across the cytoplasmic membrane. A strong dependence of copper uptake on the incubation medium was observed in the absence of DMP. The mainmore »« less
https://doi.org/10.1128/AAC.21.6.881

Similar Records

Title: Direct Evidence of Visible Light-Induced Homolysis in Chlorobis(2,9-dimethyl-1,10-phenanthroline)copper(II)

Abstract

Citation Formats

Visible-Light Photocatalysis: Does It Make a Difference in Organic Synthesis? journal, June 2018

Photoredox Catalysis in Organic Chemistry journal, June 2016

Recent progress in the development of transition-metal based photoredox catalysts journal, February 2020

Copper’s rapid ascent in visible-light photoredox catalysis journal, May 2019

Heteroleptic Copper(I)-Based Complexes for Photocatalysis: Combinatorial Assembly, Discovery, and Optimization journal, April 2018

Transient Absorption Dynamics of Sterically Congested Cu(I) MLCT Excited States journal, March 2015

Design of a Long-Lifetime, Earth-Abundant, Aqueous Compatible Cu(I) Photosensitizer Using Cooperative Steric Effects journal, July 2013

Making Copper Photocatalysis Even More Robust and Economic: Photoredox Catalysis with [Cu II (dmp) 2 Cl]Cl: Making Copper Photocatalysis Even More Robust and Economic: Photoredox Catalysis with [Cu II (dmp) 2 Cl]Cl journal, July 2019

Visible‐Light‐Accelerated Copper(II)‐Catalyzed Regio‐ and Chemoselective Oxo‐Azidation of Vinyl Arenes journal, July 2018

Photolyses of Metal Compounds: Cupric Chloride in Organic Media journal, June 1962

3 d-d Excited States of Ni(II) Complexes Relevant to Photoredox Catalysis: Spectroscopic Identification and Mechanistic Implications journal, March 2020

Exploring Chromium(III)−Alkyl Bond Homolysis with CpCr[(ArNCMe) 2 CH](R) Complexes journal, December 2010

Photoredox behaviour of chlorocopper(II) complexes in acetonitrile: mechanism and quantum yields journal, January 1979

Photochemistry of copper(II) chlorocomplexes in acetonitrile: Trapping the ligand-to-metal charge transfer excited state relaxations pathways journal, November 2014

Electron spin resonance of .beta.-chloroalkyl nitroxides. Angular dependence of .beta.-chlorine hyperfine coupling journal, July 1970

On the spin trapping of chlorine atoms. Competition from chloride ions journal, July 1991

Ultrafast Structural Rearrangements in the MLCT Excited State for Copper(I) bis- Phenanthrolines in Solution journal, February 2007

Electronic structures of ion radicals of nitrogen-heteroaromatic hydrocarbons as studied by ESR and optical spectroscopy journal, November 1979

Trap-Free Halogen Photoelimination from Mononuclear Ni(III) Complexes journal, May 2015

Ultraviolet/visible spectra of halogen molecule/arene and halogen atom/arene .pi.-molecular complexes journal, January 1989

Transient Charge-transfer Complexes with Chlorine Atoms by Pulse Radiolysis of Carbon Tetrachloride Solutions journal, June 1967

Selective functionalization of methane, ethane, and higher alkanes by cerium photocatalysis journal, July 2018

Ligand-Accelerated Iron Photocatalysis Enabling Decarboxylative Alkylation of Heteroarenes journal, May 2019

Visible-Light Photocatalysis: Does It Make a Difference in Organic Synthesis?
journal, June 2018

Photoredox Catalysis in Organic Chemistry
journal, June 2016

Recent progress in the development of transition-metal based photoredox catalysts
journal, February 2020

Copper’s rapid ascent in visible-light photoredox catalysis
journal, May 2019

Heteroleptic Copper(I)-Based Complexes for Photocatalysis: Combinatorial Assembly, Discovery, and Optimization
journal, April 2018

Transient Absorption Dynamics of Sterically Congested Cu(I) MLCT Excited States
journal, March 2015

Design of a Long-Lifetime, Earth-Abundant, Aqueous Compatible Cu(I) Photosensitizer Using Cooperative Steric Effects
journal, July 2013

Making Copper Photocatalysis Even More Robust and Economic: Photoredox Catalysis with [Cu ^II (dmp) ₂ Cl]Cl: Making Copper Photocatalysis Even More Robust and Economic: Photoredox Catalysis with [Cu ^II (dmp) ₂ Cl]Cl
journal, July 2019

Visible‐Light‐Accelerated Copper(II)‐Catalyzed Regio‐ and Chemoselective Oxo‐Azidation of Vinyl Arenes
journal, July 2018

Photolyses of Metal Compounds: Cupric Chloride in Organic Media
journal, June 1962

³ d-d Excited States of Ni(II) Complexes Relevant to Photoredox Catalysis: Spectroscopic Identification and Mechanistic Implications
journal, March 2020

Exploring Chromium(III)−Alkyl Bond Homolysis with CpCr[(ArNCMe) ₂ CH](R) Complexes
journal, December 2010

Photoredox behaviour of chlorocopper(II) complexes in acetonitrile: mechanism and quantum yields
journal, January 1979

Photochemistry of copper(II) chlorocomplexes in acetonitrile: Trapping the ligand-to-metal charge transfer excited state relaxations pathways
journal, November 2014

Electron spin resonance of .beta.-chloroalkyl nitroxides. Angular dependence of .beta.-chlorine hyperfine coupling
journal, July 1970

On the spin trapping of chlorine atoms. Competition from chloride ions
journal, July 1991

Ultrafast Structural Rearrangements in the MLCT Excited State for Copper(I) bis- Phenanthrolines in Solution
journal, February 2007

Electronic structures of ion radicals of nitrogen-heteroaromatic hydrocarbons as studied by ESR and optical spectroscopy
journal, November 1979

Trap-Free Halogen Photoelimination from Mononuclear Ni(III) Complexes
journal, May 2015

Ultraviolet/visible spectra of halogen molecule/arene and halogen atom/arene .pi.-molecular complexes
journal, January 1989

Transient Charge-transfer Complexes with Chlorine Atoms by Pulse Radiolysis of Carbon Tetrachloride Solutions
journal, June 1967

Selective functionalization of methane, ethane, and higher alkanes by cerium photocatalysis
journal, July 2018

Ligand-Accelerated Iron Photocatalysis Enabling Decarboxylative Alkylation of Heteroarenes
journal, May 2019