Regioselectivity in the photodimerization of 9-hydroxy-methylanthracene and 9-anthracene carboxylic acid esters in surfactant systems

Schütz, Andreas; Wolff, Thomas

doi:10.1016/s1010-6030(97)00145-7

Cited by 17 publications

(5 citation statements)

References 29 publications

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“…Photodimerization of acenaphthylene and coumarin, the photocycloaddition of acenaphthylene to acryolonitrile, and the photocycloaddition of cyclohexenone to isobutylene are a few examples that illustrate the local concentration effect of micelles (Scheme ). − …”

Section: Micelles As Reaction Mediamentioning

confidence: 99%

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Supramolecular Photochemistry as a Potential Synthetic Tool: Photocycloaddition

2016

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Photochemistry, bearing significant applications in natural and man-made events such as photosynthesis, vision, photolithography, photodynamic therapy, etc., is yet to become a common tool during the synthesis of small molecules in a laboratory. Among other rationale, the inability to influence photochemical reactions with temperature, solvent, additives, etc., dissuades chemists from employing light-initiated reactions as a routine synthetic tool. This review highlights how diverse, highly organized structures such as solvent-free crystals and water-soluble host-guest assemblies can be employed to control and manipulate photoreactions and thereby serve as an efficient tool for chemists, including those interested in synthesis. The efficacy of the media in modifying the excited-state behavior of organic molecules is illustrated with photocycloaddition in general and [2 + 2] photocycloaddition in particular, reactions widely employed in the synthesis of complex natural products as well as highly constrained molecules, as exemplars. The reaction media, highly pertinent in the context of green sustainable chemistry, include solvent-free crystals and solids such as silica, clay, and zeolite and water-soluble hosts that can solubilize and preorganize hydrophobic reactants in water. Since no other reagent would be more sustainable than light and no other medium greener than water, we believe that the supramolecular photochemistry expounded here has a momentous role as a synthetic tool in the future.

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Section: Micelles As Reaction Mediamentioning

confidence: 99%

“…A similar orientation of isophorone, 9-substituted anthracenes, 2-alkoxynaphthalenes, and 2-pyridones in micellar solution can be invoked to explain the high regioselective photodimerization (Schemes , , , and ; Table ). ,,− …”

Section: Micelles As Reaction Mediamentioning

confidence: 99%

Supramolecular Photochemistry as a Potential Synthetic Tool: Photocycloaddition

2016

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“…These types of polymer have been crosslinked easily by the irradiation of UV light and used as printing inks, photoresist plates, coating materials, 1 liquid crystals, 2 tissue engineering, 3 biosensors, 4 UV-curing adhesives, 5 hole transporting materials in organic light emitting diodes 6 and optical anisotropy. 7 The polymers containing photosensitive moiety such as cinnamate, 8 chalcone, 9 stilbene 10 maleimide and anthracene 11 easily go through photo crosslinking upon irradiation . The rate of photocrosslinking of acrylate polymers was fast under mild conditions and used in several applications.…”

Section: Introductionmentioning

confidence: 99%

Acrylate polymers of triazine containing chalcone moiety: Synthesis, characterization, reactivity ratio and photocrosslinking studies

Suresh

Arun

2022

Polymers and Polymer Composites

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Acrylate monomer ((4-(3-(4-((4-(4-(3-(2,4-dichlorophenyl)-3-oxoprop-1-en-1-yl)phenoxy)-6-((4-nitrophenyl)amino)-1,3,5-triazin-2-yl)oxy)phenyl)-3-oxoprop-1-en-1-yl)phenyl acrylate (DTCP) is prepared and used to prepare poly (DTCP) and its copolymer poly (DTCP-co-HEA) and poly (DTCP-co-S) using 2-hydroxyethyl acrylate (HEA), styrene (S) by solution polymerization technique. Infrared spectroscopy (FT-IR), proton Nucleharmar Magnetic Resonance (1H NMR), and UV-Visible techniques are used to identify the synthesized polymers. Gel permeation chromatography method is used to determine the polymer’s weight average molecular weight, which is found to be around 10000 g/mol. According to the Thermo Gravimetric Analysis study, the synthesized polymers go through single stage decomposition centered at 340°C. The polymer reactivity ratio is found using well known Finemann-Ross (F-R), Kelen-Tudos (K-T), and extended Kelen-Tudos (ex.K-T) methods. The reactivity of the commercial monomers (HEA or S) is found to be higher than that of synthesized monomer, according to our findings. The photocrosslinking rate of the synthesized polymers is determined using a UV visible spectroscopic method and found to be high for polymer having HEA unit.

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“…The UV-induced [2+2]-cycloaddition, as applied in this work, provides a destruction-poor pathway for cross-linking, since wavelength and applied energy entry can easily be controlled. There are many UV-cross-linkable groups for monomers, as N-alkyl-3,4-dimethylmaleimide (DMI) [29], anthracene [30,31], stilbene [32], cinnamic acid [33,34], uracil derivatives [35], coumarin [36,37] or for polymers alkene groups [38]. All of them cross-link via [2+2]-cycloaddition.…”

Section: Introductionmentioning

confidence: 99%

Tailoring Confinement: Nano-Carrier Synthesis via Z-RAFT Star Polymerization

2015

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Abstract:A new pathway to nano-sized hollow-sphere particles from six-arm star polymers with an amphiphilic core-corona structure, synthesized in a four-step-procedure by means of reversible addition-fragmentation chain transfer (RAFT) polymerization is presented, in order to achieve more stable and versatile nano-container systems, which could be applied in the fields of drug delivery or catalyst storage. Star-shaped amphiphilic, diblock copolymers serve as globular platforms for synthesizing uniform hollow structures. By the introduction of monomer units carrying UV-cross-linkable dimethyl maleimido functionalities into the outer sphere of these star polymers, the carrier's shell could be stabilized under UV-irradiation. After removal of the RAFT-core-constituting the central hub of the star polymer-by aminolysis, the carrier is ready for loading.

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Regioselectivity in the photodimerization of 9-hydroxy-methylanthracene and 9-anthracene carboxylic acid esters in surfactant systems

Cited by 17 publications

References 29 publications

Supramolecular Photochemistry as a Potential Synthetic Tool: Photocycloaddition

Supramolecular Photochemistry as a Potential Synthetic Tool: Photocycloaddition

Acrylate polymers of triazine containing chalcone moiety: Synthesis, characterization, reactivity ratio and photocrosslinking studies

Tailoring Confinement: Nano-Carrier Synthesis via Z-RAFT Star Polymerization

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