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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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| Item type | Article | ||||
| Journal or Publication Title | Frontiers in Chemistry | ||||
| Publisher | Frontiers | ||||
| Open Access Type | Gold (with APC) | ||||
| Place of Publication | LAUSANNE | ||||
| Volume | 10 | ||||
| Page Range | p. 983342 | ||||
| Date | 28 September 2022 | ||||
| Date of publication | 21 Oct 2022 13:13 | ||||
| Institutions | Chemistry and Pharmacy > Institut für Physikalische und Theoretische Chemie > Chair of Physical Chemistry I > Prof. Dr. Patrick Nürnberger | ||||
| Identification Number |
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| Keywords | TRANS-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 Classification | 500 Science > 540 Chemistry & allied sciences | ||||
| Status | Published | ||||
| Refereed | Yes, this version has been refereed | ||||
| Created at the University of Regensburg | Yes | ||||
| URN of the UB Regensburg | urn:nbn:de:bvb:355-epub-530931 | ||||
| Item ID | 53093 |
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