Substrate induced catalysis: Deciphering the weak acid triggered bleaching of an angular terthiazole photochromic dye

Nagakawa, T.; Serpentini, Charles Louis; Coudret, Christophe; Micheau, J. C.; Kawai, Tsuyoshi

doi:10.1016/j.dyepig.2010.03.024

Cited by 6 publications

(2 citation statements)

References 18 publications

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“…The photobleaching of solutions is well described by straight lines, whereas the photocoloration kinetics required complex equations. On the other hand, Nagakawa and coworkers 14 have investigated the thermal bleaching of the ring‐closed isomer of an angular terthiazole photochromic diarylethene induced by acid in acetonitrile and have determined a sigmoid shape in the absorbance versus time plot.…”

Section: Introductionmentioning

confidence: 99%

Photokinetics of two novel photochromic diarylethenes derived from benzothiophene

Vázquez

Nudelman

2012

Int J of Chemical Kinetics

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Two new unsymmetrically substituted photochromic diarylethenes, namely 3- [3, 3,4,4,5,5-hexafluoro-2-(2-methylbenzothien-3-yl)cyclopent-1-en-1-yl]-2-methyl-6-methoxy-1benzothiophene and 3-[3,3,4,4,5,5-hexafluoro-2-(2-methylbenzothien-3-yl)cyclopent-1-en-1yl]-2-methyl-6-methoxy-7-nitro-1-benzothiophene, were synthesized. Their optical properties and kinetics of cyclization and cycloreversion were determined in four solvents and compared with the symmetrical diarylethene (3,3,4,4,5,5-hexafluorocyclopent-1-en-1,2-diyl)bis(2-methyl-1-benzothiophene). While the UV spectra of the three compounds are almost insensitive to solvent changes, the rates of the ring-opening and ring-closure reactions exhibit interesting kinetic behavior that differs from other diarylethenes reported in the literature. The cycloreversion for the three compounds follows first-order kinetics, whereas the cyclization cannot be described by a simple kinetic law. Different approaches were tested, and a complex exponential equation could be derived that fits the experimental data. The unusual presence of two ring-opened conformational isomers, one of them nonphotochromic, is proposed for the ring-opened compounds to explain the derived kinetic law and observed solvent effects. These results are of interest in relation to the application of the novel diarylethenes as potential optical materials. C 2012 Wiley Periodicals, Inc. Int J Chem Kinet 44: [736][737][738][739][740][741][742][743][744] 2012

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Section: Introductionmentioning

confidence: 99%

Photokinetics of two novel photochromic diarylethenes derived from benzothiophene

Vázquez

Nudelman

2012

Int J of Chemical Kinetics

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“…Photochromic compounds have attracted remarkable research interests because of their potential applications in photonic switch device, erasable-memory media, optical data storage and photo-drive actuators by taking advantage of their outstanding thermally irreversible and fatigueresistant photochromic capabilitis [1][2][3][4][5][6]. Spirobenzopyrans, azobenzenes, fulgides and diarylethene moieties have been employed in literatures [7][8][9]. Among those known photochromic system, diarylethene bearing two thienyl-derived groups is the best candidate because it is especially well suited as switching units [1,2,10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Photochromic Properties of a Novel Diarylethene Derivative

Zheng

Fan

et al. 2011

AMR

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A new red diarylethene compound, 1,2-bis[2-n-hexyl-5-hydroxymethyl -3-thienyl]-perfluorocyclopentene (1o), was synthesized and its photochemic properties and fluorescence were studied. Specifically, photochromism in solution and in poly-methylmethacrylate (PMMA) amorphous films were investigated. The results showed that it exhibited good photochromism in both solution and PMMA amorphous film under photoirradiation. In addition, the compound exhibited relatively strong fluorescence that can be useful for the design of the fluorescence molecule switch.

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Gated Photochromism and Acidity Photomodulation of a Diacid Dithienylethene Dye

Massaad

Micheau

Coudret

et al. 2012

Chemistry A European J

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The present study quantitatively analyses the gated photochromism and the acidity photomodulation properties of a diacid dithienylethene compound. Photoisomerisation between the open and closed isomers was investigated by UV/visible and (1)H NMR spectroscopy. It was found that the photocyclisation quantum yield of the diacid form was remarkably high (around 90%). Partial neutralisation of the open isomer revealed a gated photochromism as the photocyclisation quantum yield of the mono- and dianion were 50 and 67%, respectively. A considerable photomodulation of the acidity was observed: the closed isomer is more acid than the open one by more than one pK(a) unit. This effect has been shown to be exploitable for a reversible photo-acid generation. This is the first time that a complete quantitative investigation that allows for the determination of the main photochromic, spectral and thermodynamic parameters of a base-sensitive photochromic diarylethene has been carried out.

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Substrate induced catalysis: Deciphering the weak acid triggered bleaching of an angular terthiazole photochromic dye

Cited by 6 publications

References 18 publications

Photokinetics of two novel photochromic diarylethenes derived from benzothiophene

Photokinetics of two novel photochromic diarylethenes derived from benzothiophene

Synthesis and Photochromic Properties of a Novel Diarylethene Derivative

Gated Photochromism and Acidity Photomodulation of a Diacid Dithienylethene Dye

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