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

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

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

Veröffentlichungsdatum dieses Volltextes: 21 Okt 2022 13:13
Artikel
DOI zum Zitieren dieses Dokuments: 10.5283/epub.53093


Zusammenfassung

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

DokumentenartArtikel
Titel eines Journals oder einer ZeitschriftFrontiers in Chemistry
Verlag:Frontiers
Ort der Veröffentlichung:LAUSANNE
Band:10
Seitenbereich:S. 983342
Datum28 September 2022
InstitutionenChemie und Pharmazie > Institut für Physikalische und Theoretische Chemie > Lehrstuhl für Physikalische Chemie I > Prof. Dr. Patrick Nürnberger
Identifikationsnummer
WertTyp
10.3389/fchem.2022.983342DOI
Stichwörter / 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-Dezimal-Klassifikation500 Naturwissenschaften und Mathematik > 540 Chemie
StatusVeröffentlicht
BegutachtetJa, diese Version wurde begutachtet
An der Universität Regensburg entstandenJa
URN der UB Regensburgurn:nbn:de:bvb:355-epub-530931
Dokumenten-ID53093

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