Monitoring the photochemistry of a formazan over 15 orders of magnitude in time
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 respi...
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| Format: | Article |
| Language: | English |
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Frontiers Media S.A.
2022-09-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/articles/10.3389/fchem.2022.983342/full |
| _version_ | 1828175054941192192 |
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| author | Svenja Wortmann Roger Jan Kutta Patrick Nuernberger |
| author_facet | Svenja Wortmann Roger Jan Kutta Patrick Nuernberger |
| author_sort | Svenja Wortmann |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-12T04:22:02Z |
| format | Article |
| id | doaj.art-1fc9592bdbaa43ed81561977cb47def6 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-04-12T04:22:02Z |
| publishDate | 2022-09-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-1fc9592bdbaa43ed81561977cb47def62022-12-22T03:48:11ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462022-09-011010.3389/fchem.2022.983342983342Monitoring the photochemistry of a formazan over 15 orders of magnitude in timeSvenja WortmannRoger Jan KuttaPatrick Nuernberger2,3,5-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.https://www.frontiersin.org/articles/10.3389/fchem.2022.983342/fullformazanphotoisomerizationtransient absorptionfemtochemistrystreak cameraexcited-state dynamics |
| spellingShingle | Svenja Wortmann Roger Jan Kutta Patrick Nuernberger Monitoring the photochemistry of a formazan over 15 orders of magnitude in time Frontiers in Chemistry formazan photoisomerization transient absorption femtochemistry streak camera excited-state dynamics |
| title | Monitoring the photochemistry of a formazan over 15 orders of magnitude in time |
| title_full | Monitoring the photochemistry of a formazan over 15 orders of magnitude in time |
| title_fullStr | Monitoring the photochemistry of a formazan over 15 orders of magnitude in time |
| title_full_unstemmed | Monitoring the photochemistry of a formazan over 15 orders of magnitude in time |
| title_short | Monitoring the photochemistry of a formazan over 15 orders of magnitude in time |
| title_sort | monitoring the photochemistry of a formazan over 15 orders of magnitude in time |
| topic | formazan photoisomerization transient absorption femtochemistry streak camera excited-state dynamics |
| url | https://www.frontiersin.org/articles/10.3389/fchem.2022.983342/full |
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