A temperature-mapping molecular sensor for polyurethane-based elastomers

Mason, Brian P.; Whittaker, Michael R.; Hemmer, James R.; Arora, Sanjiv; Harper, Alice C.; Alnemrat, Sufian; McEachen, A.; Helmy, Sameh; Alaniz, Javier Read de; Hooper, Joseph P.

doi:10.1063/1.4940750

Cited by 57 publications

(56 citation statements)

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“…Importantly, these sensors could be reversibly activated by using light. In another study, Hopper and co‐workers took advantage of the thermochromic properties of the zwitterionic form of the switch and fabricated sensors for mapping temperature localization with microscale precision . By replacing the aliphatic amines with aromatic ones, these researchers developed an improved family of switches, which could operate in a wide range of organic solvents .…”

Section: Introductionmentioning

confidence: 99%

Irreversible Bleaching of Donor–Acceptor Stenhouse Adducts on the Surfaces of Magnetite Nanoparticles

et al. 2017

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Two novel donor–acceptor Stenhouse adducts (DASAs) featuring the catechol moiety were synthesized and characterized. Both compounds bind strongly to the surfaces of magnetite nanoparticles. An adrenaline‐derived DASA renders the particles insoluble in all common solvents, likely because of poor solvation of the zwitterionic isomer generated on the nanoparticle surfaces. Well‐soluble nanoparticles were successfully obtained using dopamine‐derived DASA equipped with a long alkyl chain. Upon its attachment to nanoparticles, this DASA undergoes an irreversible decoloration reaction owing to the formation of the zwitterionic form. The reaction follows first‐order kinetics and proceeds more rapidly on large nanoparticles. Interestingly, decoloration can be suppressed in the presence of free DASA molecules in solution or at high nanoparticle concentrations.

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Section: Introductionmentioning

confidence: 99%

Irreversible Bleaching of Donor–Acceptor Stenhouse Adducts on the Surfaces of Magnetite Nanoparticles

et al. 2017

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“…This new class of photoswitchable molecules is synthetically versatile and exhibits a unique combination of physical and chemical properties with excellent fatigue resistance under ambient conditions. They can be used for light‐mediated cargo release, dynamic phase‐transfer materials, and temperature‐mapping molecular sensors …”

Section: Introductionmentioning

confidence: 99%

“…However, most research has been focused on low molecular weight organic compounds. To use such low molecular weight materials in practical applications, the common method is to prepare solid films using a doped polymer matrix, but the aggregation tendency of the small guest organic molecules in the polymer is a general problem. One possible way to overcome this disadvantage is by synthesizing polymers with relatively high molecular weights, which can be conveniently fabricated into films just by a spin coating process.…”

Section: Introductionmentioning

confidence: 99%

Polystyrene Based Visible Light Responsive Polymer with Donor-Acceptor Stenhouse Adduct Pendants

Sinawang

Wang

et al. 2016

Macromol. Chem. Phys.

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A polystyrene based visible light responsive polymer bearing donor–acceptor Stenhouse adduct (DASA) pendants is designed and synthesized. Styrene‐vinylbenzyl chloride copolymer (PS‐co‐PCMS) is prepared by free radical polymerization. Then amino‐functionalized PS‐co‐PCMS is obtained by the nucleophilic substitution reaction between the chloromethyl unit and n‐butylamine. Finally, the prepared secondary amines of the polymer are reacted with 5‐(furan‐2‐ylmethylene)‐2,2‐dimethyl‐1,3‐dioxane‐4,6‐dione to fully change them into DASA pendants. The final DASA‐containing polymer shows a tunable photoswitching property upon irradiation with visible light. A photoinduced contact angle change of water on the spin‐coated film of DASA polymer is observed. The DASA polymer film shows excellent photolithographic performance, with well‐defined patterns being efficiently photofabricated using a suitable mask.

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“…[6][7][8][9] The equilibrium between the two forms is dependent on the solvente nvironment andt he structural motifs of the DASA derivatives, consistingo fa ne lectron donor and an acceptorm oiety,r esultingi napush-pull system.U pon irradiation, the equilibrium is shifted towardst he ring cyclized isomer (cyclized form) and, upon thermalr elaxation, it returns to the initialc onjugated state (linear form). [8,9,14,15] The inherent advantages of DASA photoswitches, which includesn egative photochromism, inexpensives tarting materials, modular synthesis, tunable absorption, visible-light switching, and good fatiguer esistance, are appealing for ar ange of applications.T odate, polarity and color are the main adjustable propertieso fD ASAs explored for applications including micelles formation, targeting biomedical applications, [4,16] pH and temperature sensors, [5,17] and visible-light responsive devices. [32] The current consensus on the cyclization processi nvolves isomerizationo ft he double bonds, followedby ab ond rotation, and finallyathermal conrotatory4 p electrocyclization leading to the cyclized ring, commonly stabilizedb yi ts zwitterionic form through ap roton transfer.…”

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confidence: 99%

It's a Trap: Thiol‐Michael Chemistry on a DASA Photoswitch

Alves

Wiedbrauk

Gräfe

et al. 2020

Chemistry A European J

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Donor-acceptor Stenhousea dducts( DASA) are popularp hotoswitches capable of togglingb etween two isomersd epending on the light and temperature of the system.T he cyclized polar form is accessed by visible-light irradiation, whereas the linear nonpolar form is recovered in the dark. Upon the formation of the cyclized form,t he DASA contains ad ouble bond featuring a b-carbonp rone to nucleophilica ttack.H ere, an isomer selective thiol-Michael reaction betweenthe cyclized DASA and ab ase-activated thiol is introduced. The thiol-Michael addition was carried out with an alkyl (1-butanethiol) and an aromatic thiol (p-bromothiophenol) as reaction partners, both in the presence of ab ase. Undero ptimized conditions,t he reactionp roceeds preferentially in the presenceo fl ight and base. The current study demonstrates that DASAsc an be selectively trapped in their cyclized state.Molecular photoswitches undergo reversible isomerization upon irradiation with light, and sometimes in combination with ad ifferent stimulus, for example, temperature. [1] Light, as ar eadily available and adjustable reactiont rigger,i sp articularly interesting for implementing spatiotemporal control on reaction outcomes. For example, photoswitches are employed for biomedical andb iochemical processes including targetedd rug delivery and chemical/biological sensing applications. [2][3][4][5] Photoswitches, such as derivatives of the donor-acceptor Stenhouse adduct (DASA), coexisti na ne quilibrium between two isomeric forms.O ne isomer consists of an intensely colored (blue, purple or orange)n onpolar linear form, whereas the other isomer is cyclized, polar,c olorless and commonly zwitterionic (Scheme 1). [6][7][8][9] The equilibrium between the two forms is dependent on the solvente nvironment andt he structural motifs of the DASA derivatives, consistingo fa ne lectron donor and an acceptorm oiety,r esultingi napush-pull system.U pon irradiation, the equilibrium is shifted towardst he ring cyclized isomer (cyclized form) and, upon thermalr elaxation, it returns to the initialc onjugated state (linear form). The cyclization mechanism hasbeen clarified in ac areful study by Feringa and Buma,i nw hichd ensity functional theory calculationsa nd transient absorption kinetics measurements were employed. [32] The current consensus on the cyclization processi nvolves isomerizationo ft he double bonds, followedby ab ond rotation, and finallyathermal conrotatory4 p electrocyclization leading to the cyclized ring, commonly stabilizedb yi ts zwitterionic form through ap roton transfer. [10][11][12][13] Clarification of the cyclization mechanism resulted in ap ool of DASA photoswitches bearing avariety of acceptorand donor functionalitiesaswell as an improvedk nowledge of factors influencing the switching process. [8,9,14,15] The inherent advantages of DASA photoswitches, which includesn egative photochromism, inexpensives tarting materials, modular synthesis, tunable absorption, visible-light switching, and good fatiguer esistance, are appealing for ar ...

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A temperature-mapping molecular sensor for polyurethane-based elastomers

Cited by 57 publications

References 10 publications

Irreversible Bleaching of Donor–Acceptor Stenhouse Adducts on the Surfaces of Magnetite Nanoparticles

Irreversible Bleaching of Donor–Acceptor Stenhouse Adducts on the Surfaces of Magnetite Nanoparticles

Polystyrene Based Visible Light Responsive Polymer with Donor-Acceptor Stenhouse Adduct Pendants

It's a Trap: Thiol‐Michael Chemistry on a DASA Photoswitch

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