Ratiometric Singlet Oxygen Detection in Water Using Acene-Doped Conjugated Polymer Nanoparticles

Abstract

Although fluorescent probes for the detection of singlet oxygen (O) have been an active area of research, most such probes rely upon change in intensity of a single band. Herein, we report a FRET-based, O-sensitive aqueous suspension of conjugated polymer nanoparticles (CPNs) comprising the energy-donating host polymer poly[{9,9-dioctyl-2,7-divinylene-fluorenylene}-alt-co-{2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene}] doped with an energy acceptor, the O-sensitive thienoacene 5,12-bis(4-methoxyphenyl)-2-butyltetraceno[2,3-b]thiophene. Using a phthalocyanine-based sensitizer, IRDye 700DX, our probe shows a rapid, ratiometric response to photosensitized O in water in both cuvettes and 96-well plates that compares favorably to the commercial O-sensitive dye, singlet oxygen sensor green. The response to irradiation of even nanomolar concentrations of photosensitizer demonstrates the sensitivity of our ratiometric probe.

31P NMR Evidence for Peroxide Intermediates in Lipid Emulsion Photooxidations: Phosphine Substituent Effects in Trapping

“…At 90 J cm −2 , the percent yield of 2 oxide decreased from 9.3% to 5% with decreasing AlPcS concentration from 100 μ m to 10 n m . Photoactivity of sensitizers in nanomolar quantities is of interest in the field of PDT , and while our data show 5% photooxidation at 10 n m concentrations of AlPcS, effects such as the location of the sensitizer in Intralipid were not assessed.…”

Uric Acid: A Less‐than‐Perfect Probe for Singlet Oxygen

“…Although other water-soluble probes for O 2 (a 1 D g ) are available (16,17,19,20,31), these molecules likewise have selected disadvantages. As such, there is still a need to develop and characterize a wider range of O 2 (a 1 D g ) probes.…”

“…The advantages of using an optical spectroscopic approach in this regard should be apparent. Although activity to this end is as old as O 2 (a 1 D g ) itself, it remains an active field of research (15)(16)(17)(18)(19)(20), certainly with respect to the goal of elucidating the intracellular behavior of O 2 (a 1 D g ) in time-and spatially resolved experiments. Sadly, it is our impression that UA has acquired the stature of an "ideal" water-soluble probe for O 2 (a 1 D g ), likely by virtue of longevity in its use.…”

Singlet oxygen imaging using fluorescent probe Singlet Oxygen Sensor Green in photosynthetic organisms

“…Thus developing new 1 O 2 sensors remained a goal of research teams. In chemical systems, more alternatives to SOSG exist, including FRET-based ratiometric monitoring of 1 O 2 with acene-doped conjugated polymer nanoparticles 30 or 1 O 2 detection in solutions by Bodipy-based energy transfer cassette 31 . Recently, Tang et al .…”