Unimolecular photochemistry of anthracenes

Becker, Hans Dieter

doi:10.1021/cr00017a008

Cited by 382 publications

(287 citation statements)

References 129 publications

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“…The photochemistry of anthracene and its derivatives has been widely studied [3,[21][22][23][24]. Anthracene has four distinct UV absorption bands in the wavelength range of 275-325 nm and an irradiation by wavelengths higher than 350 nm induces a (4π + 4π) cycloaddition reaction leading to the formation of a photodimer.…”

Section: Introductionmentioning

confidence: 99%

Photoresponsive Cellulose Nanocrystals

Filpponen

Sadeghifar

Argyropoulos

2011

Nanomaterials and Nanotechnology

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In this communication a method for the creation of fluorescent cellulose nanoparticles using click chemistry and subsequent photodimerization of the installed sidechains is demonstrated. In the first step, the primary hydroxyl groups on the surface of the CNCs were converted to carboxylic acids by using TEMPO-mediated hypohalite oxidation. The alkyne groups, essential for the click reaction, were introduced into the surface of TEMPOoxidized CNCs via carbodiimide-mediated formation of an amide linkage between monomers carrying an amine functionality and carboxylic acid groups on the surface of the TEMPO-oxidized CNCs. Finally, the reaction of surface-modified TEMPO-oxidized cellulose nanocrystals and azido-bearing coumarin and anthracene monomers were carried out by means of a click chemistry, i.e., Copper(I)-catalyzed Azide-Alkyne Cycloaddition (CuAAC) to produce highly photo-responsive and fluorescent cellulose nanoparticles. Most significantly, the installed coumarin and/or anthracene side-chains were shown to undergo UV-induced [2+2] and [4+4] cycloaddition reactions, bringing and locking the cellulose nanocrystals together. This effort paves the way towards creating, cellulosic photo responsive nano-arrays with the potential of photo reversibility since these reactions are known to be reversible at varying wavelengths.

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Section: Introductionmentioning

confidence: 99%

Photoresponsive Cellulose Nanocrystals

Filpponen

Sadeghifar

Argyropoulos

2011

Nanomaterials and Nanotechnology

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“…The well-documented anthracene photodimerisation process (see Figure 2) was monitored by the decrease in absorbance of the characteristic monomer band at 275 nm and an accompanying increase in absorbance at 263 nm assigned to the photodimer. At 365 nm, the dimer does not absorb significantly and reverse dimer-to-monomer reaction is minimal [25]. The isosbestic point of the spectra at ~294 nm is not particularly clean indicating that the dimerisation reaction occurs with some side reactions.…”

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confidence: 94%

Synthesis and Characterization of Anthracene-2,6-dithioacetate: a Rigid, Conjugated Molecule for the Formation of Monolayers on Gold

2008

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“…These reversible properties are based on the photodimerization reaction. Anthracene photodimerization is one of the oldest best known photochemical reactions which was reported by Fritzche et al [1][2][3][4][5][6][7].…”

Section: Introductionmentioning

confidence: 99%

Photodimerization of thioxanthone–anthracene: formation of monochromophoric Type II initiator

Balta

Arsu

2016

Designed Monomers and Polymers

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Thioxanthone-anthracene (TX-A) was previously synthesized and used as an initiator for the polymerization of acrylates and methacrylates in air atmosphere. Photodimerization of TX-A was carried out in benzene under light irradiation of >350 nm, and dimer (diTX-A) formation was followed by UV-vis, fluorescence and phosphorescence spectroscopy. The conjugation of anthracene was destroyed after dimerization, and the thioxanthone group was left behind. Therefore, the typical thioxanthone absorption spectrum was seen at 380 nm. TX-A itself does not have phosphorescence emission; however, diTX-A displayed phosphorescence emission spectrum similar to thioxanthone. IR and 1 H NMR spectrophotometric techniques also helped to determine the structure of diTX-A. Furthermore, photopolymerization of methyl methacrylate (MMA) in the presence of dimer (diTX-A) was another proof of the photodimerization of TX-A. diTX-A initiated polymerization of MMA as good as thioxanthone in the nitrogen atmosphere and displayed typical Type II initiator behaviour.

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Unimolecular photochemistry of anthracenes

Cited by 382 publications

References 129 publications

Photoresponsive Cellulose Nanocrystals

Photoresponsive Cellulose Nanocrystals

Synthesis and Characterization of Anthracene-2,6-dithioacetate: a Rigid, Conjugated Molecule for the Formation of Monolayers on Gold

Photodimerization of thioxanthone–anthracene: formation of monochromophoric Type II initiator

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