Telluropyrylium dyes. 1. 2,6-Diphenyltelluropyrylium dyes

Abstract

Methine and polymethine dyes containing at least one 2,6-diphenyltelluropyrylo group as well as another 2,6-diphenylchalcogenopyrylo group have been prepared by the condensation of 2,6-diphenyI-4-methylchalcogenopyrylium, salts with 4/7-2,6-diphenyltelluropyran-4-one or (4/7-2,6-diphenyltelluropyran-4-ylidene)acetaldehyde or by the reaction of 2,6-diphenyl-4-metiiyltelluropyrylium tetrafluoroborate with bisaldehyde equivalents. Similarly, various iVJV-dialkylamino-containing telluropyrylium dyes have also been prepared. The telluropyrylium dyes absorb at longer wavelengths than their oxygen, sulfur, or selenium counterparts. This shift can be empirically correlated with an increase in electropositive character of the heteroatom.

Chalcogenopyrylium Dyes as Differential Modulators of Organic Anion Transport by Multidrug Resistance Protein 1 (MRP1), MRP2, and MRP4

“…Five of 7 compounds (V-1, V-2, V-5, V-6, V-7) comprising a fifth class of structurally distinct CGPs ( Fig. 2A) were selected from a library of chalcogenopyrylium methine and trimethine dyes, previously prepared by literature methods for evaluation as photosensitizers (Detty and Murray, 1982;Powers et al, 1989;Detty et al, 1990;Bellnier et al, 1999). Two additional class V CGPs (V-3, V-4) were synthesized as follows [using starting materials as described (Anderson and Stang, 1976;Leonard et al, 1999;Simard et al, 2000)]: 1) uptake by MRP1-enriched inside-out membrane vesicles (tested at a single concentration of 30 mM except for CGP I-2, which was tested at 5 mM; data from Ebert et al, 2012).…”

Flavylium Polymethine Fluorophores for Near‐ and Shortwave Infrared Imaging

“…[19] Extending heterocycle conjugation or adding electron-donating groups has been shown to bathochromically shift polymethine dyes. [21] Collectively,t hese fundamental studies give insight into fluorophore design, which we looked to apply to the benchmark SWIR polymethine,the thiaflavylium dye IR-26. [21] Collectively,t hese fundamental studies give insight into fluorophore design, which we looked to apply to the benchmark SWIR polymethine,the thiaflavylium dye IR-26.…”

Photosensitization of human glioma cells by chalcogenapyrylium dyes

“…1 for compound structures. bDye synthesis is described in references [21] and [22]. escein reflect structural changes in the mitochondria as a result of treating tumor cells with growth inhibitors [17].…”

“…It is possible to create CP dyes that maximally absorb light in the near infrared range of the spectrum ( Table 1, Fig. 1) by controlling various structural features in the dyes [21,22], The heavier the chalcogen atom in the dye chromophore, the longer will be the wavelength of absorption of the dye. Thus, the incorporation of selenium and/or tellurium into the dye chromophore gives longer wavelength-absorbing materials.…”