Photopolymerization of 7,7?-coumarinyl polymethylene dicarboxylates: Fluorescence and kinetic study

Chen, Yun; Hong, Rong‐Tzung

doi:10.1002/(sici)1099-0518(199710)35:14<2999::aid-pola21>3.0.co;2-d

Cited by 26 publications

(35 citation statements)

References 22 publications

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“…[12] In this photoinduced electron-transfer process,t he charge is transferred during the irradiation from the lone pair of electrons located on the oxygen atom of THF to the excited coumarin. [13] The reduced triplet excited state population decreased the likelihood of the formation of anti-CDs and accelerated the formation of syn-CDs.T he fluorescence decay of the singlet excimer moieties after 365-nm light irradiation for 4h indicates that singlet excimers contribute substantially to the formation of syn-CDs. [13] The reduced triplet excited state population decreased the likelihood of the formation of anti-CDs and accelerated the formation of syn-CDs.T he fluorescence decay of the singlet excimer moieties after 365-nm light irradiation for 4h indicates that singlet excimers contribute substantially to the formation of syn-CDs.…”

Section: Angewandte Chemiementioning

confidence: 99%

Light‐Induced Reversible Self‐Assembly of Gold Nanoparticles Surface‐Immobilized with Coumarin Ligands

Mao

Cai

et al. 2015

Angew Chem Int Ed

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A novel light-induced reversible self-assembly (LIRSA) system is based on the reversible photodimerization and photocleavage of coumarin groups on the surface of gold nanoparticles (AuNPs) in THF solution. Facilitated by coumarin groups, light irradiation at 365 nm triggers the stable assembly of monodisperse AuNPs; the resulting self-assembly system can be disassembled back to the disassembled state by a relatively short exposure to benign UV light. The reversible self-assembly cycle can be repeated 4 times. A specific concentration range of coumarin ligand and the THF solvent were identified to be the two predominant factors that contribute to the LIRSA of AuNPs. This is the first successful application of reversible photodimerization based on a coumarin derivative in the field of AuNP LIRSA. This LIRSA system may provide unique opportunities for the photoregulated synthesis of many adjustable nanostructures and devices.

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Section: Angewandte Chemiementioning

confidence: 99%

Light‐Induced Reversible Self‐Assembly of Gold Nanoparticles Surface‐Immobilized with Coumarin Ligands

Mao

Cai

et al. 2015

Angew Chem Int Ed

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“…In this photoinduced electron‐transfer process, the charge is transferred during the irradiation from the lone pair of electrons located on the oxygen atom of THF to the excited coumarin. The simplified energy level diagram for coumarin dimerization in THF solution under 350‐nm irradiation is shown in Figure c. The singlet excimers contribute to the longer singlet lifetime and the low efficiency of intersystem crossing from the singlet state to the triplet state . The reduced triplet excited state population decreased the likelihood of the formation of anti ‐CDs and accelerated the formation of syn ‐CDs.…”

Section: Figurementioning

confidence: 99%

Light‐Induced Reversible Self‐Assembly of Gold Nanoparticles Surface‐Immobilized with Coumarin Ligands

Mao

Cai

et al. 2015

Angewandte Chemie

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A novel light‐induced reversible self‐assembly (LIRSA) system is based on the reversible photodimerization and photocleavage of coumarin groups on the surface of gold nanoparticles (AuNPs) in THF solution. Facilitated by coumarin groups, light irradiation at 365 nm triggers the stable assembly of monodisperse AuNPs; the resulting self‐assembly system can be disassembled back to the disassembled state by a relatively short exposure to benign UV light. The reversible self‐assembly cycle can be repeated 4 times. A specific concentration range of coumarin ligand and the THF solvent were identified to be the two predominant factors that contribute to the LIRSA of AuNPs. This is the first successful application of reversible photodimerization based on a coumarin derivative in the field of AuNP LIRSA. This LIRSA system may provide unique opportunities for the photoregulated synthesis of many adjustable nanostructures and devices.

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“…1,2 Under alternative illumination with two different wavelengths, coumarins are known to be able to undergo reversible photodimerization (4310 nm) and cleavage (o250 nm) through two-photon absorption of visible light. 1,2 Under alternative illumination with two different wavelengths, coumarins are known to be able to undergo reversible photodimerization (4310 nm) and cleavage (o250 nm) through two-photon absorption of visible light.…”

Section: Introductionmentioning

confidence: 99%

Nanocapsules for 5-fluorouracil delivery decorated with a poly(2-ethylhexyl methacrylate-co-7-(4-trifluoromethyl)coumarin acrylamide) cross-linked wall

et al. 2015

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The first synthesis of polymer vesicles with reverse cross-linked walls from poly[2-ethylhexylmethacrylateco-(7-(4-trifluoromethyl)coumarin acrylamide)] P(EHMA/FMCA) is reported. The synthesis, carried out under UV light (l = 350 nm), was achieved via radical photopolymerization of hydrophobic compounds saturating the bilayer of 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) liposome template. The polymerization reaction with coumarin moieties has a pivotal role, because the polymer chains become cross-linked as a result of the dimerization of the coumarin side chains of the formed polymers and, in this way, spherical capsules are obtained. Moreover, thanks to the incorporation of coumarin moieties, as an additional bonus, a nanometer-thick porous, fluorescent wall was formed, avoiding the use of additional cross-linking reagents, which might deactivate the encapsulated payloads. We present a new paradigm of release drug delivery systems combining a long shelf-life with the ability for rapid release using external factors such as light. To demonstrate this concept, target compounds such as hydrophilic dyes (Lucifer yellow (LY), phenosafranin (PhS)) and the drug 5-fluorouracil (5-FU)) were incorporated inside the stable, hollow, polymeric nanocapsules. The goal of these applications depends on the versatile strategy that is used for the preparation of highly emissive nanometer-sized polymer capsules with surface functionalities and optical properties for diagnostic applications.

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Photopolymerization of 7,7?-coumarinyl polymethylene dicarboxylates: Fluorescence and kinetic study

Cited by 26 publications

References 22 publications

Light‐Induced Reversible Self‐Assembly of Gold Nanoparticles Surface‐Immobilized with Coumarin Ligands

Light‐Induced Reversible Self‐Assembly of Gold Nanoparticles Surface‐Immobilized with Coumarin Ligands

Light‐Induced Reversible Self‐Assembly of Gold Nanoparticles Surface‐Immobilized with Coumarin Ligands

Nanocapsules for 5-fluorouracil delivery decorated with a poly(2-ethylhexyl methacrylate-co-7-(4-trifluoromethyl)coumarin acrylamide) cross-linked wall

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