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

Noirbent, Guillaume; Xu, Yangyang; Bonardi, Aude-Héloise; Duval, Sylvain; Gigmès, Didier; Lalevée, Jacques; Dumur, Frédéric

doi:10.3390/molecules25102317

Cited by 22 publications

(20 citation statements)

References 67 publications

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“…Therefore, DASAs are also attractive to be NIR photoinitiators for the radical polymerization. [ 85 ] Oms and coworkers reported photopolymerization using DASAs modified polyoxometalate (POM‐DASAs) and N ‐methyldiethanolamine as the photoinitiator, while polyethylene glycol diacrylate was used as the monomers. The polymerization proceeds fast under light irradiation, and finally generates elastomers with young modulus of ~6.67 MPa.…”

Section: Other Sensitive Behaviors and Applicationmentioning

confidence: 99%

Learning from Spiropyrans: How to Make Further Developments of Donor‐Acceptor Stenhouse Adducts

et al. 2021

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Photoresponsive| Donor-acceptor Stenhouse adducts| Spiropyrans| Applications| Isomerization Donor-acceptor Stenhouse adducts (DASAs) as a species of novel photochromic molecules, have been developing rapidly and attracting broad researchers' sights since 2014. DASAs show visible/near-infrared (NIR) light induced linear-to-cyclic isomerization and heat induced cyclic-to-linear isomerization, therefore they are attractive in photoresponsive hydrogels, drug delivery, cell culturing and tissue engineering. As a series of well-known photoresponsive molecules, spiropyrans (SPs) show similar molecular properties and comparable photoswitching with DASAs. UV light triggers closed-to-open (also known as spirocyclic (SC)-to-merocyanine (MC)) isomerization of SPs, while the reversed open-to-closed isomerization occurs under visible light or heat. Light irradiation switches the molecular color, scale, geometry, and polarity of SPs and DASAs reversibly. Since the researches on DASAs are still in the infancy, the chemical structures, isomerization mechanisms and potential applications need to be further investigated and explored. The well-studied SPs have important reference values to the comprehensive developments of DASAs. In the present review, we summarized, compared and discussed SPs and DASAs with regards to their molecular structures, synthesis, photoswitching and applications. We also make our perspective on the developments of DASA in future. Yongli Duan (lest) is a Ph.D. student at University of Electronic Science and Technology of China. She is focusing on the synthesis, photoresponsive mechanisms and properties of DASAs under supervision of Prof. Dr. Dongsheng Wang.

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Section: Other Sensitive Behaviors and Applicationmentioning

confidence: 99%

Learning from Spiropyrans: How to Make Further Developments of Donor‐Acceptor Stenhouse Adducts

et al. 2021

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“…All target chromophores 1-4 except 2 d [41] are new compounds. However, several structural analogues with a different N-alkyl thiobarbituric unit are known; namely analogues of 1 a-e, [58][59][60][61] 2 a, 2 c, 2 d, [34,40,[62][63][64] 3 a, [62,65] and 4 a, 4 c. [40,[62][63][64]66] The preparations and characterizations of new aldehydes 7 c, 7 e, and 8 e are given in the SI. The starting aldehydes 5 a-e, 6 a, 7 a, and 8 a as well as N,N'dibutyl-2-thiobarbituric acid (DBTBA) are commercially available.…”

Section: Experimental Section General Methodsmentioning

confidence: 99%

“…All target chromophores 1 – 4 except 2 d [41] are new compounds. However, several structural analogues with a different N ‐alkyl thiobarbituric unit are known; namely analogues of 1 a – e , [58–61] 2 a , 2 c , 2 d , [34,40,62–64] 3 a , [62,65] and 4 a , 4 c [40,62–64,66] . The preparations and characterizations of new aldehydes 7 c , 7 e , and 8 e are given in the SI.…”

Section: Methodsmentioning

confidence: 99%

Small Heterocyclic D‐π‐D‐π‐A Push‐Pull Molecules with Complex Electron Donors

et al. 2021

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A large series of small push-pull chromophores based on electron-withdrawing N,N'-dibutylthiobarbituric acid has been designed and successfully synthesized. The electron donating part involves common mesomeric donors such as methoxy, N,N-dimethylamino, N,N-diphenylamino, and piperidin-1-yl groups. Five-membered heteroaromatics, namely thiophene, Nmethylpyrrole, and furan have been employed as electron rich π-linkers and auxiliary donors. Structural analogues bearing aromatic 1,4-phenylene linker were also synthesized for comparison. Fundamental thermal and optoelectronic properties were studied by differential scanning calorimetry, cyclic voltammetry, and absorption spectroscopy. Thorough structureproperty relationships were elucidated, focusing mostly on type of the used π-linker and donor. All experimental conclusions are corroborated by theoretical calculations. The study has shown that a complex donor moiety may be built by properly combining mesomeric and auxiliary donors. Whereas strong mesomeric donor (amino) suppresses the donating effect of auxiliary donors/π-linkers, a combination of weak donor (methoxy) appended at a five-membered heterocycle pronounces the donating ability of the latter.

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“…[ 4 ] All these windows offer, at different scales, a deeper light penetration than UV or visible light in materials, especially in biological tissues in which minimal absorption is observed. Due to the properties mentioned above, NIR light has quickly become one of the main research topics in multiple fields such as coatings, [ 5 ] photopolymerization, [ 6–8 ] optics, [ 9 ] photochemically assisted synthesis, [ 10 ] and in medical applications. Notably, NIR light is a powerful tool that can be advantageously used for bioprinting while applying a minimally invasive or noninvasive approach.…”

Section: Introductionmentioning

confidence: 99%

Near‐Infrared PhotoInitiating Systems: Photothermal versus Triplet–Triplet Annihilation‐Based Upconversion Polymerization

Caron

Noirbent

Gigmès

et al. 2021

Macromol. Rapid Commun.

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NIR light‐induced polymerization has attracted more and more attention in the photopolymerization field due to the possibility to use safer and more penetrating wavelengths, reducing the hazardousness. Here, a novel perspective for the free radical polymerization of acrylate‐based monomers based on triplet–triplet annihilation upconversion (TTA‐UC) is proposed, avoiding the introduction of heavy metals, usually required in the TTA processes. Thermal imaging experiments and Fourier transform infrared spectroscopy are respectively used to record the temperature during NIR irradiation and measure the reactive function conversion. The competition between the TTA‐UC and the NIR photothermal activation is investigated to compare the relative efficiency of both NIR processes. In view of the results obtained by the different methods, the photothermal effect seems to get the upper hand over the photoactivation of the system.

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

Cited by 22 publications

References 67 publications

Learning from Spiropyrans: How to Make Further Developments of Donor‐Acceptor Stenhouse Adducts

Learning from Spiropyrans: How to Make Further Developments of Donor‐Acceptor Stenhouse Adducts

Small Heterocyclic D‐π‐D‐π‐A Push‐Pull Molecules with Complex Electron Donors

Near‐Infrared PhotoInitiating Systems: Photothermal versus Triplet–Triplet Annihilation‐Based Upconversion Polymerization

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