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Wortmann, Svenja ; Kutta, Roger Jan ; Nuernberger, Patrick

Monitoring the photochemistry of a formazan over 15 orders of magnitude in time

Article

Wortmann, Svenja, Kutta, Roger Jan and Nuernberger, Patrick (2022) Monitoring the photochemistry of a formazan over 15 orders of magnitude in time. Frontiers in Chemistry 10, p. 983342.

DOI to cite this document: 10.5283/epub.53093


Abstract

2,3,5-triphenyltetrazolium chloride (TTC) may convert into phenyl-benzo[c]tetrazolocinnolium chloride (PTC) and 1,3,5-triphenylformazan (TPF) under irradiation with light. The latter reaction, albeit enzymatically rather than photochemically, is used in so-called TTC assays indicating cellular respiration and cell growth. In this paper, we address the photochemistry of TPF with time-resolved ...

2,3,5-triphenyltetrazolium chloride (TTC) may convert into phenyl-benzo[c]tetrazolocinnolium chloride (PTC) and 1,3,5-triphenylformazan (TPF) under irradiation with light. The latter reaction, albeit enzymatically rather than photochemically, is used in so-called TTC assays indicating cellular respiration and cell growth. In this paper, we address the photochemistry of TPF with time-resolved spectroscopy on various time scales. TPF is stabilized by an intramolecular hydrogen bond and switches photochemically via an E-Z isomerization around an N=N double bond into another TPF-stereoisomer, from which further isomerizations around the C=N double bond of the phenylhydrazone group are possible. We investigate the underlying processes by time-resolved spectroscopy in dependence on excitation wavelength and solvent environment, resolving several intermediates over a temporal range spanning 15 orders of magnitude (hundreds of femtoseconds to hundreds of seconds) along the reaction path. In a quantum-chemical analysis, we identify 16 stable ground-state isomers and discuss which ones are identified in the experimental data. We derive a detailed scheme how these species are thermally and photochemically interconnected and conclude that proton transfer processes are involved.



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Details

Item typeArticle
Journal or Publication TitleFrontiers in Chemistry
PublisherFrontiers
Open Access TypeGold (with APC)
Place of PublicationLAUSANNE
Volume10
Page Rangep. 983342
Date28 September 2022
Date of publication21 Oct 2022 13:13
InstitutionsChemistry and Pharmacy > Institut für Physikalische und Theoretische Chemie > Chair of Physical Chemistry I > Prof. Dr. Patrick Nürnberger
Identification Number
ValueType
10.3389/fchem.2022.983342DOI
KeywordsTRANS-AZOBENZENE; RESONANCE RAMAN; CIS-AZOBENZENE; COLORIMETRIC ASSAY; ULTRAFAST DYNAMICS; ABSORPTION-SPECTRA; PHOTOISOMERIZATION; MECHANISM; CONFIGURATIONS; ISOMERIZATION; formazan; photoisomerization; transient absorption; femtochemistry; streak camera; excited-state dynamics; proton transfer; ground-state dynamics
Dewey Decimal Classification500 Science > 540 Chemistry & allied sciences
StatusPublished
RefereedYes, this version has been refereed
Created at the University of RegensburgYes
URN of the UB Regensburgurn:nbn:de:bvb:355-epub-530931
Item ID53093

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