The Light Emitter of the 2-Coumar­anone Chemiluminescence: Theoretical and Experimental Elucidation of a Possible Model for Bioluminescent Systems

Stefan Schramm, Isabelle Navizet, Pance Naumov, Naba K. Nath, Romain Berraud-Pache, Pascal Oesau, Dieter Weiss, Rainer Beckert

Research output: Contribution to journalArticle

Abstract

The bioluminescence reaction of many biological subspecies, most notably fireflies, forms dioxetanone derivatives as high-energy intermediates. The thermal instability of dioxetanones complicates understanding of the transition from the ground state to the first excited state that leads to light emission. Herein, we report the reaction mechanism of 2-coumaranones, synthetically accessible strongly chemiluminescent materials that mimic the bioluminescence reaction. The pathways of chemiexcitation and photorelaxation are clarified on the basis of synthetic evidence and spectrochemical as well as computational mechanistic analysis.

Original languageEnglish (US)
Pages (from-to)678-681
Number of pages4
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number4
DOIs
StatePublished - Feb 1 2016

Fingerprint

Bioluminescence
Chemiluminescence
chemiluminescence
bioluminescence
emitters
Light emission
Electron transitions
fireflies
Excited states
Ground state
thermal instability
Derivatives
light emission
ground state
excitation
2-coumaranone
dioxetanone
energy
Hot Temperature

Keywords

  • Bioluminescence
  • Luminescence
  • Natural products
  • Oxygen heterocycles
  • Photochemistry
  • Reaction mechanisms

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

The Light Emitter of the 2-Coumar­anone Chemiluminescence : Theoretical and Experimental Elucidation of a Possible Model for Bioluminescent Systems. / Schramm, Stefan; Navizet, Isabelle; Naumov, Pance; Nath, Naba K.; Berraud-Pache, Romain; Oesau, Pascal; Weiss, Dieter; Beckert, Rainer.

In: European Journal of Organic Chemistry, Vol. 2016, No. 4, 01.02.2016, p. 678-681.

Research output: Contribution to journalArticle

Schramm, Stefan ; Navizet, Isabelle ; Naumov, Pance ; Nath, Naba K. ; Berraud-Pache, Romain ; Oesau, Pascal ; Weiss, Dieter ; Beckert, Rainer. / The Light Emitter of the 2-Coumar­anone Chemiluminescence : Theoretical and Experimental Elucidation of a Possible Model for Bioluminescent Systems. In: European Journal of Organic Chemistry. 2016 ; Vol. 2016, No. 4. pp. 678-681.
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