Stable Activated Furan and Donor–Acceptor Stenhouse Adduct Polymer Conjugates as Chemical and Thermal Sensors

Chen, Qiaonan; Diaz, Yvonne J.; Hawker, Michael C.; Martinez, Michael E.; Page, Zachariah A.; Zhang, Sean Xiao‐An; Hawker, Craig J.; Alaniz, Javier Read de

doi:10.1021/acs.macromol.9b00533

Cited by 57 publications

(53 citation statements)

References 63 publications

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“…The photoisomerization of DASAs results in changes in solubility, polarity, and structure which are attractive for applications in many fields of chemistry. To date, these applications have included drug delivery, [ 19–21 ] surface modifications, [ 22,23 ] photo‐patterning, [ 24–26 ] catalyst recycling, [ 27 ] gate and molecular logic, [ 28–30 ] sensors, [ 31–35 ] nanoreactors, [ 36 ] and aggregation induced emission (AIE) materials. [ 37 ]…”

Section: Methodsmentioning

confidence: 99%

Visible Light—Responsive Drug Delivery Nanoparticle via Donor–Acceptor Stenhouse Adducts (DASA)

Yap

Zhang

Lovegrove

et al. 2020

Macromol. Rapid Commun.

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Stimuli‐responsive drug release from a nanocarrier triggered by light enables the control of the amount of drug locally. Here, block copolymer micelles based on poly(ethylene glycol) methyl ether methacrylate (PEGMEMA) as the hydrophilic block and a polymer with pendant donor–acceptor Stenhouse adducts (DASA) are used as a means to trigger the release of drugs under green light. The micelles are loaded with ellipticine to yield light‐responsive nanoparticles with sizes of around 35 nm according to transmission electron microscopy (TEM) analysis. Two micelles with a drug loading content of 4.75 and 7.4 wt% are prepared, but the micelle with the higher drug loading content leads to substantial protein adsorption. The release of ellipticine from the micelle, which is monitored using the polarity‐sensitive fluorescence of ellipticine, can be switched on by light and off by thermal recovery of DASA in the dark. The micelles are readily taken up by Michigan Cancer Foundation‐7 breast cancer cells. Subsequent light irradiation leads to enhanced drug release inside the cell as seen by the enhanced fluorescence.

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Section: Methodsmentioning

confidence: 99%

Visible Light—Responsive Drug Delivery Nanoparticle via Donor–Acceptor Stenhouse Adducts (DASA)

Yap

Zhang

Lovegrove

et al. 2020

Macromol. Rapid Commun.

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“…The kinetics of photopolymerization of the photosensitive resins were followed through the double bond C=C conversion vs. time upon NIR irradiation (see Figure 7). The peak followed by Real Time Fourier Transform Infrared (RT-FTIR) spectroscopy (using a Jasco 4600 instrument, Jasco, Tokyo, Japan) is located at 6100-6220 cm −1 as presented in [37]; this peak corresponds to the first overtone of the C-H vibrations of the =CH 2 acrylate group. The NIR photoinitiating systems are composed of (NIR) dyes (DASA1-DASA13, PP25 or PP26) combined with an iodonium salt (Ar 2 I + .PF 6 ), a phosphine (4-dppba) and a thermal initiator (here BlocBuilder MA) (see Figure 7) to take advantage of the photoinitiating system (NIR dye/iodonium/phosphine) associated with the photothermal system (NIR dye/BlocBuilder MA) as presented for other NIR dyes in [64].…”

Section: Photopolymerization Experimentsmentioning

confidence: 99%

“…Since 2014, several applications have been found for these molecular photoswitches such as the development of light-responsive drug delivery systems [34,35], liquid crystals [36], or colorimetric sensors [37,38]. To the best of our knowledge, DASA have never been reported as polymerization photoinitiators, despite the fact their strong absorption in the visible region makes these dyes ideal candidates for such an application.…”

Section: Introductionmentioning

confidence: 99%

New Donor-Acceptor Stenhouse Adducts as Visible and Near Infrared Light Polymerization Photoinitiators

Noirbent

Bonardi

et al. 2020

Molecules

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Polymerization photoinitiators that can be activated under low light intensity and in the visible range are being pursued by both the academic and industrial communities. To efficiently harvest light and initiate a polymerization process, dyes with high molar extinction coefficients in the visible range are ideal candidates. In this field, Donor-acceptor Stenhouse Adducts (DASA) which belong to a class of recently discovered organic photochromic molecules still lack practical applications. In this work, a series of DASA-based dyes are proposed as photoinitiators for the free radical polymerization of (meth)acrylates upon exposure to a near infrared light (laser diode at 785 nm).

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“…In general, two strategies including polymerization of pre‐functionalized monomers and post‐polymerization modification can be used to prepare the desired polymeric sensors. [ 52,69–74 ]…”

Section: Food Sensors Based On Polymer–dye Compositesmentioning

confidence: 99%

Functional Polymers and Polymer–Dye Composites for Food Sensing

Zhang

Chan-Park

Wang

2020

Macromol. Rapid Commun.

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The sensitive, safe, and portable detection of food spoilage is becoming unprecedentedly important because it is closely related to the public health and economic development, particularly given the globalization of food supply chain. However, the existing approaches for food monitoring are still limited to meet these requirements. To address this challenge, much research has been done to develop an ideal food sensor that can indicate food quality in real‐time in a sensitive and reliable way. So far, many sensors such as time–temperature indicators, smart trademarks, colorimetric tags, electronic noses, and electronic tongues, have been developed and even commercialized. In this feature article, the recent progress of food sensors based on functional polymers, including the molecular design of polymer structures, sensing mechanisms, and relevant processing techniques to fabricate a variety of food sensor devices is reviewed.

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Stable Activated Furan and Donor–Acceptor Stenhouse Adduct Polymer Conjugates as Chemical and Thermal Sensors

Cited by 57 publications

References 63 publications

Visible Light—Responsive Drug Delivery Nanoparticle via Donor–Acceptor Stenhouse Adducts (DASA)

Visible Light—Responsive Drug Delivery Nanoparticle via Donor–Acceptor Stenhouse Adducts (DASA)

New Donor-Acceptor Stenhouse Adducts as Visible and Near Infrared Light Polymerization Photoinitiators

Functional Polymers and Polymer–Dye Composites for Food Sensing

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