PONy dyes: Direct addition of P(III) nucleophiles to organic fluorophores.

Butkevich, A.; Sednev, M. V.; Shojaei, H.; Belov, V. N.; Hell, S. W.

doi:10.1021/acs.orglett.8b00270

Item

ITEM ACTIONSEXPORT

Add to Basket

Local TagsRelease HistoryDetailsSummary

Released

Journal Article

PONy dyes: Direct addition of P(III) nucleophiles to organic fluorophores.

MPS-Authors

/persons/resource/persons191595

Butkevich, A.
Department of NanoBiophotonics, MPI for Biophysical Chemistry, Max Planck Society;

/persons/resource/persons45941

Sednev, M. V.
Department of NanoBiophotonics, MPI for Biophysical Chemistry, Max Planck Society;

/persons/resource/persons204190

Shojaei, H.
Department of NanoBiophotonics, MPI for Biophysical Chemistry, Max Planck Society;

/persons/resource/persons14832

Belov, V. N.
Department of NanoBiophotonics, MPI for Biophysical Chemistry, Max Planck Society;

/persons/resource/persons15210

Hell, S. W.
Department of NanoBiophotonics, MPI for Biophysical Chemistry, Max Planck Society;

External Resource

No external resources are shared

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

Fulltext (public)

There are no public fulltexts stored in PuRe

Supplementary Material (public)

2540116_Suppl.pdf
(Supplementary material), 14MB

Citation

Butkevich, A., Sednev, M. V., Shojaei, H., Belov, V. N., & Hell, S. W. (2018). PONy dyes: Direct addition of P(III) nucleophiles to organic fluorophores. Organic Letters, 20(4), 1261-1264. doi:10.1021/acs.orglett.8b00270.

Cite as: https://hdl.handle.net/21.11116/0000-0000-7047-2

Abstract

Nucleophilic addition of phosphinic acid, phosphites, sodium dialkyl phosphites, phosphoramidites, phosphinites, and phosphonites to highly polarized or cationic fluorophores, followed by oxidation, results in new “PONy” dyes with auxochromic phosphinate, phosphonate, or phosphonamidate groups. The reaction was applied to a wide variety of coumarins, (thio)pyronins, and N-alkylacridinium and 5,6-dihydrobenzo[c]xanthen-12-ium salts as well as a meso-chlorinated BODIPY to provide compact dyes with red-shifted absorption and emission bands and Stokes shifts up to 8200 cm–1.