Molecular design of fluorescent pH sensors based on reduced rhodol by structure-pKa relationship for imaging of lysosome

More, Kunal N.; Mun, Seul-Ki; Kang, Julie; Kim, Jong-Jin; Yee, Sung‐Tae; Chang, Daesung

doi:10.1016/j.dyepig.2020.108785

Cited by 22 publications

(13 citation statements)

References 37 publications

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“…1 H and No. 2 H. Compared with the acid‐response structural switching of Rhodol, [ 35 ] the acid‐responsive mechanism of R‐Rhodol‐A was demonstrated in Figure S7 (Supporting Information). This unique acid‐responsive CPL‐switchable property laid the basis for preparation of electrically switchable thin‐film devices based on “electroacid” method and PCET mechanism.…”

Section: Resultsmentioning

confidence: 99%

A Flexible Circularly Polarized Luminescence Switching Device Based on Proton‐Coupled Electron Transfer

et al. 2022

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Flexible circularly polarized luminescence (CPL) switching devices have been long‐awaited due to their promising potential application in wearable optoelectronic devices. However, on account of the few materials and complicated design of manufacturing systems, how to fabricate a flexible electric‐field‐driven CPL‐switching device is still a serious challenge. Herein, a flexible device with multiple optical switching properties (CPL, circular dichroism (CD), fluorescence, color) is designed and prepared efficiently based on proton‐coupled electron transfer (PCET) mechanism by optimizing the chiral structure of switching molecule. More importantly, this device can maintain the switching performance even after 300 bending‐unbending cycles. It has a remarkable comprehensive performance containing bistable property, low open voltage, and good cycling stability. Then, prototype devices with designed patterns have been fabricated, which opens a new application pattern of CPL‐switching materials.

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Section: Resultsmentioning

confidence: 99%

A Flexible Circularly Polarized Luminescence Switching Device Based on Proton‐Coupled Electron Transfer

et al. 2022

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“…It is hypothesized that, compared to AYR-E, the longer substituents, that is, PnBuOx-AYR 5 and PnBuOx-AYR 10, destabilized the deprotonated chromophore (anion) more by their increased hydrophobicity (thus decreased polarity) [63][64][65][66][67] or, to a smaller extent, via steric and electrostatic (donating) effects. [58,[68][69][70][71][72][73][74][75] Hydrophobic-induced pK a -shifts have indeed been reported for proteins and polymers in solution. [63][64][65][66][67] The hydrophobic environment led to stronger bonding of the proton, resulting in the need for more extreme conditions, that is, higher pH, to deprotonate and consequently change color.…”

Section: Influence Of the Chromophore-substituentmentioning

confidence: 99%

Eco‐Friendly Colorimetric Nanofiber Design: Halochromic Sensors with Tunable pH‐Sensing Regime Based on 2‐Ethyl‐2‐Oxazoline and 2‐n‐Butyl‐2‐Oxazoline Statistical Copolymers Functionalized with Alizarin Yellow R

Schoolaert

Merckx

Becelaere

et al. 2021

Adv Funct Materials

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Colorimetric nanofibers provide visual, easy-to-interpret sensors for personal use as well as advanced applications. The potential of 2-n-butyl-2-oxazoline (B) and 2-ethyl-2-oxazoline (E) statistical copolymers as a universal, versatile support platform for nanofibrous halochromic sensor design is demonstrated. These polymers are electrospinnable from eco-friendly solvent systems, while wettability, moist adsorption capacity, and water-solubility of the membranes can be easily tuned by changing the B/E monomer ratio, ensuring wide applicability. The halochromic sensing functionality is introduced by incorporating the alizarin yellow R (AYR) chromophore, which is covalently modified with an ethyl ester-group or a short poly(2-n-butyl-2-oxazoline) chain, which is demonstrated to simultaneously prevent dye-leaching and allows tuning of the halochromic pH-sensing window. The colorimetric nanofibrous sensors reversibly respond toward aqueous solutions of different pH, (hydrochloric) acid and alkaline (ammonia) vapors, and several biogenic amines with detection limits as low as 5 ppb. Tunability of sensor responsivity, sensitivity, and pKa via manipulation of dye-polymer interactions, determined by support polymer structure and semi-crystallinity, as well as the chain length of the AYR-modified polymer, are discussed. Preliminary proof-of-principle studies indicate the potential of the developed sensors for sub-ppm biogenic amine vapor detection, which may serve as the basis for future applications in food packaging or breath analysis.

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“…Lowered extracellular pH is an important signature strongly associated with cancer invasion, progression, and metastasis. However, its malignant effects were mainly identified using cell and tissue studies 99 , 100 . Thus, monitoring pH levels in living organs is critical for providing information on the physiological and pathological processes 101 - 104 .…”

Section: Microenvironmentmentioning

confidence: 99%

Activatable NIR-II organic fluorescent probes for bioimaging

Zhang¹,

Li²,

Ma³

et al. 2022

Theranostics

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NIR-II imaging is developed rapidly for noninvasive deep tissue inspection with high spatio-temporal resolution, taking advantage of diminished autofluorescence and light attenuation. Activatable NIR‐II fluorescence probes are widely developed to report pathological changes with accurate targeting, among which organic fluorescent probes achieve significant progress. Furthermore, the activatable NIR‐II fluorescent probes exhibited appealing characteristics like tunable physicochemical and optical properties, easy processability, and excellent biocompatibility. In the present review, we highlight the advances of activatable NIR-II fluorescence probes in design, synthesis and applications for imaging pathological changes like reactive oxygen species (ROS), reactive nitrogen species (RNS), reactive sulfur species (RSS), pH, hypoxia, viscosity as well as abnormally expressed enzymes. This non-invasive optical imaging modality shows a promising prospect in targeting the pathological site and is envisioned for potential clinical translation.

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Molecular design of fluorescent pH sensors based on reduced rhodol by structure-pKa relationship for imaging of lysosome

Cited by 22 publications

References 37 publications

A Flexible Circularly Polarized Luminescence Switching Device Based on Proton‐Coupled Electron Transfer

A Flexible Circularly Polarized Luminescence Switching Device Based on Proton‐Coupled Electron Transfer

Eco‐Friendly Colorimetric Nanofiber Design: Halochromic Sensors with Tunable pH‐Sensing Regime Based on 2‐Ethyl‐2‐Oxazoline and 2‐n‐Butyl‐2‐Oxazoline Statistical Copolymers Functionalized with Alizarin Yellow R

Activatable NIR-II organic fluorescent probes for bioimaging

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