Stable fluorescent chromophores find use in a growing number of practical applications, including their utility as laser dyes,1 emitters in light-emitting diodes,2 photoconductors,3 optical data storage,4 and optical switches.5 Stable fluorophores with high quantum yields are widely used in fluorescent sensors6 and labels.7 These became very popular lately, owing to their potential for high sensitivity at low concentration coupled with decreased cost of the required equipment.8 Recently, we have described a new class of fluorescent anion sensors bearing extended conjugated chromophores9 with incorporated 2,3-di(1H-2-pyrrolyl)quinoxaline, (DPQ), as the anion recognition element.10 Literature shows that DPQ binds anions via hydrogen bonding between pyrrole NH and anions, the hydrogen bonding nature of the DPQ−anion complex was demonstrated by 1H NMR.10a In this paper, we provide a full account of our efforts including synthesis and photophysical properties of DPQ-based fluorescent anion sensors with extended conjugated chromophores S1−S6 (Figure 1), including their benzothiadiazole precursors F1−F6, which appears to be an interesting set of highly stable fluorescent chromophores.
Aldakov, Dmitry; Palacios, Manuel A.; and Anzenbacher, Pavel Jr., "Benzothiadiazoles And Dipyrrolyl Quinoxalines With Extended Conjugated Chromophores-fluorophores And Anion Sensors" (2005). Chemistry Faculty Publications. 178.
Chemistry Of Materials