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Photophysics of flavin derivatives absorbing in the blue-green region : thioflavins as potential cofactors of photoswitches
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Marian, Christel M., Nakagawa, Setsuko, Rai-Constapel, Vidisha, Karasulu, Bora and Thiel, Walter (2014) Photophysics of flavin derivatives absorbing in the blue-green region : thioflavins as potential cofactors of photoswitches. The Journal of Physical Chemistry B, 118 (7). pp. 1743-1753. doi:10.1021/jp4098233 ISSN 1520-6106.
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Official URL: http://dx.doi.org/10.1021/jp4098233
Abstract
The purpose of this study was to find flavin derivatives with absorption maxima in the blue-green region of the visible spectrum that might be used as alternative cofactors in blue-light photoreceptors. To this end, the vertical absorption spectra of eight lumiflavin-related compounds were calculated by means of quantum chemical methods. The compounds differ from lumiflavin by the subsitution of an S atom for an O atom at the 2- and/or 4-positions of the isoalloxazine core, the substitution of an N atom for a CH group in the 6- and/or 9-positions, or an extension of the π system at the 7- and 8-positions. For the three most promising compounds, 2-thio-lumiflavin, 4-thio-lumiflavin, and 2,4-dithio-lumiflavin, the quantum chemical investigations were extended to include geometry relaxations in the excited states, rates for spin-forbidden transitions and an estimate of spectral shifts brought about by polar protic environments. We find these thiocarbonyl compounds to have very promising excited-state properties. They absorb in the blue-green wavelength regime around 500 nm, i.e., substantially red-shifted with respect to lumiflavin that is the cofactor of natural blue-light photoreceptors. Their triplet quantum yields are predicted to be close to unity while their triplet lifetimes are long enough to enable bimolecular photochemical reactions. The combination of these properties makes the thioflavins potentially suitable candidates as cofactors in biomimetic photoswitches.
Item Type: | Journal Article | ||||||
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Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||
Journal or Publication Title: | The Journal of Physical Chemistry B | ||||||
Publisher: | American Chemical Society | ||||||
ISSN: | 1520-6106 | ||||||
Official Date: | February 2014 | ||||||
Dates: |
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Volume: | 118 | ||||||
Number: | 7 | ||||||
Page Range: | pp. 1743-1753 | ||||||
DOI: | 10.1021/jp4098233 | ||||||
Status: | Peer Reviewed | ||||||
Publication Status: | Published | ||||||
Access rights to Published version: | Restricted or Subscription Access |
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