Beilstein Journal of Organic Chemistry (Sep 2019)

Synthesis and properties of sulfur-functionalized triarylmethylium, acridinium and triangulenium dyes

  • Marco Santella,
  • Eduardo Della Pia,
  • Jakob Kryger Sørensen,
  • Bo W. Laursen

DOI
https://doi.org/10.3762/bjoc.15.210
Journal volume & issue
Vol. 15, no. 1
pp. 2133 – 2141

Abstract

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Triangulenium dyes functionalized with one, two or three ethylthiol functionalities were synthesized and their optical properties were studied. The sulfur functionalities were introduced by aromatic nucleophilic substitution of methoxy groups in triarylmethylium cations with ethanethiol followed by partial or full ring closure of the ortho positions with nitrogen or oxygen bridges leading to sulfur-functionalized acridinium, xanthenium or triangulenium dyes. For all the dye classes the sulfur functionalities are found to lead to intensely absorbing dyes in the visible range (470 to 515 nm), quite similar to known analogous dye systems with dialkylamino donor groups in place of the ethylthiol substituents. For the triangulenium derivatives significant fluorescence was observed (Φf = 0.1 to Φf = 0.3).

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