ACS Publications. Most Trusted. Most Cited. Most Read

OR SEARCH CITATIONS

My Activity
Publications
CONTENT TYPES

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Am. Chem. Soc. 2009, 131, 8, 2770-2771
RETURN TO ISSUEPREVCommunicationNEXT

In Search of a Chemiluminescence 1,4-Dioxy Biradical

View Author Information
Deakin University, School of Life and Environmental Sciences, Pigdons Road, Waurn Ponds 3217, Victoria, Australia, and University of Queensland, Centre for Magnetic Resonance, St. Lucia 4072, Brisbane, Australia
[email protected]
†Deakin University.
‡University of Queensland.
Cite this: J. Am. Chem. Soc. 2009, 131, 8, 2770–2771
Publication Date (Web):February 10, 2009
https://doi.org/10.1021/ja808401p
Copyright © 2009 American Chemical Society
RIGHTS & PERMISSIONS
Article Views
3083
Altmetric
-
Citations
32
LEARN ABOUT THESE METRICS
Read OnlinePDF (88 KB)
Get e-Alerts
SUBJECTS:

Abstract

Abstract Image

Electron paramagnetic resonance spectroscopy has afforded the identification of a much postulated 1,4-dioxy biradical that occurs within the light producing pathway of peroxyoxalate chemiluminescence.

Cited By

This article is cited by 32 publications.

  1. Sandra M. da Silva, André P. Lang, Ana Paula F. dos Santos, Maidileyvis C. Cabello, Luiz Francisco M. L. Ciscato, Fernando H. Bartoloni, Erick L. Bastos, Wilhelm J. Baader. Cyclic Peroxidic Carbon Dioxide Dimer Fuels Peroxyoxalate Chemiluminescence. The Journal of Organic Chemistry 2021, 86 (17) , 11434-11441. https://doi.org/10.1021/acs.joc.1c00929
  2. Ling Yue, Ya-Jun Liu. Three S0/S1 Conical Intersections Control Electron-Transfer-Catalyzed Chemiluminescence of 1,2-Dioxetanedione. Journal of Chemical Theory and Computation 2021, 17 (6) , 3483-3494. https://doi.org/10.1021/acs.jctc.1c00356
  3. Thijs Stuyver, Bo Chen, Tao Zeng, Paul Geerlings, Frank De Proft, Roald Hoffmann. Do Diradicals Behave Like Radicals?. Chemical Reviews 2019, 119 (21) , 11291-11351. https://doi.org/10.1021/acs.chemrev.9b00260
  4. Syed Niaz Ali Shah, Aamir Hassan Shah, Xiangnan Dou, Mashooq Khan, Ling Lin, Jin-Ming Lin. Radical-Triggered Chemiluminescence of Phenanthroline Derivatives: An Insight into Radical–Aromatic Interaction. ACS Omega 2019, 4 (12) , 15004-15011. https://doi.org/10.1021/acsomega.9b01785
  5. Haiping Pan, Mingkui Wang, Yan Shen, Bin Hu. Large Magneto-Current Effect in the Electrochemical Detection of Oxalate in Aqueous Solution. The Journal of Physical Chemistry C 2018, 122 (34) , 19880-19885. https://doi.org/10.1021/acs.jpcc.8b04193
  6. Morgane Vacher, Ignacio Fdez. Galván, Bo-Wen Ding, Stefan Schramm, Romain Berraud-Pache, Panče Naumov, Nicolas Ferré, Ya-Jun Liu, Isabelle Navizet, Daniel Roca-Sanjuán, Wilhelm J. Baader, Roland Lindh. Chemi- and Bioluminescence of Cyclic Peroxides. Chemical Reviews 2018, 118 (15) , 6927-6974. https://doi.org/10.1021/acs.chemrev.7b00649
  7. Manabu Abe . Diradicals. Chemical Reviews 2013, 113 (9) , 7011-7088. https://doi.org/10.1021/cr400056a
  8. Luiz F. M. L. Ciscato, Fernando H. Bartoloni, Erick L. Bastos and Wilhelm J. Baader . Direct Kinetic Observation of the Chemiexcitation Step in Peroxyoxalate Chemiluminescence. The Journal of Organic Chemistry 2009, 74 (23) , 8974-8979. https://doi.org/10.1021/jo901402k
  9. Alexandre Pradal. Four-Membered Rings With Two Oxygen Atoms. 2022,,, 507-537. https://doi.org/10.1016/B978-0-12-818655-8.00152-9
  10. Marina A. Tzani, Dimitra K. Gioftsidou, Michael G. Kallitsakis, Nikolaos V. Pliatsios, Natasa P. Kalogiouri, Panagiotis A. Angaridis, Ioannis N. Lykakis, Michael A. Terzidis. Direct and Indirect Chemiluminescence: Reactions, Mechanisms and Challenges. Molecules 2021, 26 (24) , 7664. https://doi.org/10.3390/molecules26247664
  11. Li Mao, Hui-Ying Gao, Bo Shao, Chun-Hua Huang, Ben-Zhan Zhu. Molecular mechanisms and potential applications of the intrinsic chemiluminescence produced from the degradation of haloaromatic pollutants during environmentally-friendly advanced oxidation processes. Environmental Science: Water Research & Technology 2020, 6 (9) , 2259-2274. https://doi.org/10.1039/D0EW00325E
  12. Syed Niaz Ali Shah, Mashooq Khan, Zia Ur Rehman. A prolegomena of periodate and peroxide chemiluminescence. TrAC Trends in Analytical Chemistry 2020, 122 , 115722. https://doi.org/10.1016/j.trac.2019.115722
  13. V. N. Peters, C. Yang, S. Prayakarao, M. A. Noginov. Effect of metal–dielectric substrates on chemiluminescence kinetics. Journal of the Optical Society of America B 2019, 36 (7) , E132. https://doi.org/10.1364/JOSAB.36.00E132
  14. Yufu Tang, Xiaomei Lu, Chao Yin, Hui Zhao, Wenbo Hu, Xiaoming Hu, Yuanyuan Li, Zhen Yang, Feng Lu, Quli Fan, Wei Huang. Chemiluminescence-initiated and in situ -enhanced photoisomerization for tissue-depth-independent photo-controlled drug release. Chemical Science 2019, 10 (5) , 1401-1409. https://doi.org/10.1039/C8SC04012E
  15. Zoe M. Smith, Jacqui L. Adcock, Neil W. Barnett, Paul S. Francis. Chemiluminescence—Liquid Phase. 2018,,https://doi.org/10.1016/B978-0-12-409547-2.10936-9
  16. Benzhan Zhu, Chen Shen, Huiying Gao, Liya Zhu, Jie Shao, Li Mao. Intrinsic chemiluminescence production from the degradation of haloaromatic pollutants during environmentally-friendly advanced oxidation processes: Mechanism, structure–activity relationship and potential applications. Journal of Environmental Sciences 2017, 62 , 68-83. https://doi.org/10.1016/j.jes.2017.06.035
  17. Erick Leite Bastos, Pooria Farahani, Etelvino J.H. Bechara, Wilhelm Josef Baader. Four-membered cyclic peroxides: Carriers of chemical energy. Journal of Physical Organic Chemistry 2017, 30 (9) , e3725. https://doi.org/10.1002/poc.3725
  18. John Lee. Perspectives on Bioluminescence Mechanisms. Photochemistry and Photobiology 2017, 93 (2) , 389-404. https://doi.org/10.1111/php.12650
  19. Nicolas S. Lopes, Ariane M. Yoshitake, Adriana F. Silva, Vani X. Oliveira, Leandro S. Silva, Ana A. S. Pinheiro, Luiz Francisco M. L. Ciscato. Antimalarial Effect of 3-Methoxy-1,2-Dioxetanes on the Erythrocytic Cycle of Plasmodium falciparum. Chemical Biology & Drug Design 2015, 86 (6) , 1373-1377. https://doi.org/10.1111/cbdd.12599
  20. Alison L. McManus, Erik P. Hoy, David A. Mazziotti. Energies and structures in biradical chemistry from the parametric two-electron reduced-density matrix method: applications to the benzene and cyclobutadiene biradicals. Physical Chemistry Chemical Physics 2015, 17 (19) , 12521-12529. https://doi.org/10.1039/C5CP01310K
  21. Zhihua Wang, Fang Liu, Chao Lu. Evolution of biogenic amine concentrations in foods through their induced chemiluminescence inactivation of layered double hydroxide nanosheet colloids. Biosensors and Bioelectronics 2014, 60 , 237-243. https://doi.org/10.1016/j.bios.2014.04.013
  22. Dieter Seebach, Tomohiro Yoshinari, Albert K. Beck, Marc-Olivier Ebert, Alejandro Castro-Alvarez, Jaume Vilarrasa, Markus Reiher. How Small Amounts of Impurities Are Sufficient to Catalyze the Interconversion of Carbonyl Compounds and Iminium Ions, or Is There a Metathesis through 1,3-Oxazetidinium Ions? Experiments, Speculations, and Calculations. Helvetica Chimica Acta 2014, 97 (9) , 1177-1203. https://doi.org/10.1002/hlca.201400221
  23. Felipe A. Augusto, Glalci A. de Souza, Sergio P. de Souza Júnior, Muhammad Khalid, Wilhelm J. Baader. Efficiency of Electron Transfer Initiated Chemiluminescence. Photochemistry and Photobiology 2013, 89 (6) , 1299-1317. https://doi.org/10.1111/php.12102
  24. Luís Pinto da Silva, Joaquim C. G. Esteves da Silva. Mechanistic study of the unimolecular decomposition of 1,2-dioxetanedione. Journal of Physical Organic Chemistry 2013, 26 (8) , 659-663. https://doi.org/10.1002/poc.3149
  25. Brett I. Dunlap, Igor V. Schweigert, Andrew P. Purdy, Arthur W. Snow, Anguang Hu. Thermodynamic and kinetic stabilities of CO 2 oligomers. The Journal of Chemical Physics 2013, 138 (13) , 134304. https://doi.org/10.1063/1.4797465
  26. Takayuki Maruyama, Susumu Narita, Jiro Motoyoshiya. The Hammett correlation between distyrylbenzene substituents and chemiluminescence efficiency providing various ρ-values for peroxyoxalate chemiluminescence of several oxalates. Journal of Photochemistry and Photobiology A: Chemistry 2013, 252 , 222-231. https://doi.org/10.1016/j.jphotochem.2012.12.006
  27. B.-Z. Zhu, L. Mao, C.-H. Huang, H. Qin, R.-M. Fan, B. Kalyanaraman, J.-G. Zhu. Unprecedented hydroxyl radical-dependent two-step chemiluminescence production by polyhalogenated quinoid carcinogens and H2O2. Proceedings of the National Academy of Sciences 2012, 109 (40) , 16046-16051. https://doi.org/10.1073/pnas.1204479109
  28. Kiomars Zargoosh, Mojtaba Shamsipur, Morteza Hosseini, Claudia Caltagirone, Vito Lippolis. The fast peroxyoxalate-chemiluminescence of 3-1-aza-4,10-dithia-7-oxacyclododecane as a novel fluorophore. Journal of Luminescence 2012, 132 (8) , 2126-2129. https://doi.org/10.1016/j.jlumin.2012.03.051
  29. Abdollah Yari, Marzieh Saidikhah. Dye Doped Eosin Yellowish Silica Nanoparticles as Novel Fluorophore for a Peroxyoxalate Chemiluminescence System. Journal of Fluorescence 2012, 22 (3) , 993-1002. https://doi.org/10.1007/s10895-012-1037-1
  30. Takayuki Maruyama, Yasuyuki Fujie, Noriyuki Oya, Eisuke Hosaka, Aki Kanazawa, Daisuke Tanaka, Yoshiyuki Hattori, Jiro Motoyoshiya. Control of peroxyoxalate chemiluminescence by nitrogen-containing ligand quenching: turning off and on by ligand–metal ion host–guest interactions. Tetrahedron 2011, 67 (36) , 6927-6933. https://doi.org/10.1016/j.tet.2011.06.078
  31. Jacqui L. Adcock, Colin J. Barrow, Neil W. Barnett, Xavier A. Conlan, Conor F. Hogan, Paul S. Francis. Chemiluminescence and electrochemiluminescence detection of controlled drugs. Drug Testing and Analysis 2011, 3 (3) , 145-160. https://doi.org/10.1002/dta.236
  32. Benito Alcaide, Pedro Almendros. Four-Membered Ring Systems. 2011,,, 85-107. https://doi.org/10.1016/S0959-6380(11)22004-X

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect

This website uses cookies to improve your user experience. By continuing to use the site, you are accepting our use of cookies. Read the ACS privacy policy.

CONTINUE