Spectral-kinetic evidence of interaction of photochromic diarylethenes with silver nanoparticles

Кобелева, О. И.; Валова, Т. М.; Barachevskii, V. A.; Krayushkin, М. М.; Lichitskiĭ, B. V.; Dudinov, A. A.; Kuznetsova, O. Yu.; Adamov, G. E.; Grebennikov, E. P.

doi:10.1134/s0030400x10070167

Cited by 9 publications

(3 citation statements)

References 15 publications

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“…Namely, in the case of the 1‐(2,5‐dimethyl‐3‐thienyl)‐2‐(2‐methyl‐5‐(2,4‐difluorophenyl)) perfluorocyclopentene; and for 1‐[2‐methyl‐5‐(4‐cyanophenyl)‐3‐thienyl]‐2‐[2‐methyl‐5‐(4‐clorophenyl)‐3‐thienyl] perfluorocyclopentene, first‐order kinetics for the cycloreversion were observed . Likewise, in the investigation of the photochromism of some diarylethenes bearing sulfur‐containing sustituents with and without silver nanoparticles, also a first‐order photodecoloration in dimethylsulfoxide (DMSO) was described …”

Section: Resultsmentioning

confidence: 99%

Ring opening/closure reactions of novel diheteroarylethenes derivatives. Solvent effects

Vázquez

Nudelman

2012

J of Physical Organic Chem

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Three novel diarylethenes derived from benzothiophene were synthesized and their photochemical optical properties studied in four solvents (n‐hexane, toluene, acetonitrile and methanol). It was determined that these compounds dramatically increase the light absorption in the visible region upon exposure to UV light, showing two absorption maxima at 420 nm and 520 nm, respectively. The observed change is completely reverted upon exposure to visible light. The three compounds demonstrate negligible fatigue, excellent stability in the four solvents, and absence of photodegradation and thermal back reactions. This paper also describes a complete study of solvent effects on the kinetics of the ring opening and cycloreversion. While, the UV spectra are little sensitive both to the substitution pattern and to the solvent influence, the kinetics of ring opening/cycloreversion reactions exhibit a more interesting behavior that differs from other diarylethenes reported in the literature. The cyclization kinetics shows a complex order, well fitted by an exponential equation, while the cycloreversion presents first‐order kinetics. The whole complex reaction scheme can be explained by the unusual presence of two conformers of the open form, a parallel and an antiparallel conformation. Though other alternative mechanism could explain the kinetics, additional evidence is consistent with the conformational equilibrium proposed: i.e. the solvent influence on the kinetics of the nitro‐substituted substrate, and the double signals for the methyl protons and for the methoxy protons (when present) observed in the nuclear magnetic resonance spectra. These observations are relevant in relation to the application of these novel diarylethenes as potential optical materials. Copyright © 2012 John Wiley & Sons, Ltd.

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Section: Resultsmentioning

confidence: 99%

Ring opening/closure reactions of novel diheteroarylethenes derivatives. Solvent effects

Vázquez

Nudelman

2012

J of Physical Organic Chem

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“…Likewise, Liu and coworkers 12 have determined similar kinetic behavior for the thienyl diarylethene 1‐[2‐methyl‐5‐(4‐cyanophenyl)‐3‐thienyl]‐2‐[2‐methyl‐5‐(4‐chlorophenyl)‐3‐thienyl]‐perfluorocyclopentene. Kobeleva et al 13 have described the photochromism of some diarylethenes with sulfur‐containing substituents in DMSO with and without silver nanoparticles. The photobleaching of solutions is well described by straight lines, whereas the photocoloration kinetics required complex equations.…”

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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“…In this connection, for the first time, novel photochromic thiosemicarbazide and thiocarbazate derivatives of dithienylperfluorocyclopentenes Sch. 77 were synthesized [112].…”

Section: Scheme 76mentioning

confidence: 99%

Nanophotochromism

Barachevsky¹

2015

Organic Photonics and Photovoltaics

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Abstract:The review presents the state-of-the-art analysis of investigations in the field of a new line of research of photochromism -nanophotochromism. The design, properties, and possible applications of photochromic nanoparticles prepared by different methods with the use of photochromic substances (aggregates, host-guest, and polymer systems, solid nanoparticles) as well as core-shell photochromic nanostructures based on polymers, silica, quantum dots, doped upconversion nanocrystals, and Ag, Au, etc. nanoparticles have been reviewed. Keywords: photochromism; photochromic nanoparticles; core-shell photochromic nanoparticles design; photoswitching; aggregates; polymer systems, host-guest systems IntroductionPhotochromism is a very important phenomenon for different applications in photonics. The applications are based on reversible phototransformations of photochromic compounds between two states and changes of their properties that accompany these transformations At present, systems and materials containing photochromic nanopatricles have become highly significant. Among these are nanodimensional particles of photochromic substances, including aggregates, and coreshell systems. As a core, inorganic nanoparticles of gold, silver, metal oxides, quantum dots (QD), and also polymeric nanoparticles are used. The shell consists of photochromic molecules or their aggregates connected to a core surface either chemically or physically. Photochromic nanoparticles with photocontrolled fluorescence arouse a special interest because the fluorescence technique is becoming a leading strategy in biological diagnosis, imaging, and detection applications. This paper is a state-of-the-art review which presents results of studying photochromic nanoparticles including author's own data. The results of earlier research are also surveyed in some other reviews [1][2][3][4][5][6][7][8][9][10][11][12][13]. Photochromic nanoparticles:properties and applications Nanoparticles based on photochromic substances AggregatesThe most known photochromic nanoparticles are aggregates of photochromic organic compounds [14]. These compounds experience reversible photoinduced transformations between two states, Sch. 1A and Sch. 1B. Scheme 1The photoinduced colored merocyanine form B absorbing visible irradiation is formed from a colorless form A as a result of photodissociation of the -C-O-bond of the pyran heterocycle under UV radiation, and this is followed by spontaneous isomerization of the cis-form to the trans one. The colored form B can be converted back to the initial colorless form A upon absorption of visible light or spontaneously during the dark relaxation, which is accelerated by heating.The J-aggregates of nitro-substituted indoline spiropyrans Sch. 2 with long alkyl substituents are of special interest [15].The narrow absorption bands of J-aggregates of these photochromic compounds (Fig. 1) made it possible prepare a specimen of the multilayered optical disk providing freUnauthenticated Download

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Spectral-kinetic evidence of interaction of photochromic diarylethenes with silver nanoparticles

Cited by 9 publications

References 15 publications

Ring opening/closure reactions of novel diheteroarylethenes derivatives. Solvent effects

Ring opening/closure reactions of novel diheteroarylethenes derivatives. Solvent effects

Photokinetics of two novel photochromic diarylethenes derived from benzothiophene

Nanophotochromism

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