Abstract
Fluorophores of the acridone family have been widely employed in many applications, such as DNA sequencing, the detection of biomolecules, and the monitoring of enzymatic systems, as well as being the bases of intracellular sensors and even antitumoral agents. They have been widely used in fluorescence imaging due to their excellent photophysical properties, in terms of quantum yield and stability. However, frequently, the fluorescence emission data from acridones are not easily interpretable due to complex excited-state dynamics. The formation of π-stacking aggregates and excimers and excited-state proton transfer (ESPT) reactions usually result in emission features that are dependent on the experimental conditions. Therefore, an in-depth understanding of the dynamics involved in the excited-state transients of these dyes is mandatory for their appropriate application. Herein, we synthesized and fully characterized different 2-methoxy-9-acridone dyes. Their transient fluorescence emission spectra exhibited a complex dynamic behavior that can be linked to several excited-state reactions. We performed a thorough study of the excited-state dynamics of these dyes by means of time-resolved fluorimetry supported by computational calculations. All this allowed us to establish a multistate kinetic scheme, involving an ESPT reaction coupled to an excimer formation process. We have unraveled the rich dynamics behind this complex behavior, which provides a better understanding of the excited states of these dyes.
Highlights
Fluorescence imaging can be a valuable tool for studying biomolecules in complex biological environments because of characteristics such as its great sensitivity, high spatial resolution, and ease to use (Nalbant et al, 2004)
An in-depth knowledge of their underlying photophysical behavior is mandatory for their usage as antitumoral agents (Cholewinski et al, 2011), in photodynamic therapy or as laser and OLED active media (Sharma et al, 2016; Pander et al, 2018)
We analyzed in-depth the acid-base and spectroscopic properties, as well as the may be involved, striking excited-state dynamics were found (Figures 4–6)
Summary
Fluorescence imaging can be a valuable tool for studying biomolecules in complex biological environments because of characteristics such as its great sensitivity, high spatial resolution, and ease to use (Nalbant et al, 2004). The fluorescence lifetime is highly sensitive to Coupled Excited-State Dynamics in Acridones environmental factors, such as solvent polarity (Orte et al, 2016; Ripoll et al, 2018), conformational changes (Tomin, 2010), and excited-state reactions (Alvarez-Pez et al, 2001), among others. These characteristics together with the independence from the concentration of the fluorophore make fluorescence lifetime imaging (FLIM) an advantageous method over fluorescence intensity measurements. By applying the FLIM methodology and the single molecule approach, we have been able to evaluate the transport of extracellular phosphate into preosteoblast cells during osteoblast differentiation (Paredes et al, 2013) and to monitor pH changes within the cellular cytoplasm using pH-sensitive nanoparticles (Orte et al, 2013)
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