Photoswitchable Organic Nanoparticles and a Polymer Film Employing Multifunctional Molecules with Enhanced Fluorescence Emission and Bistable Photochromism

Lim, Seon-Jeong; An, Byeong‐Kwan; Jung, Sang Don; Chung, Myung-Ae; Park, Soo Young

doi:10.1002/anie.200461172

Cited by 482 publications

(177 citation statements)

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“…For the preparing of amphiphilic core-shell type nanoparticles, coatings of photochromic compounds have been developed [19,54,55]. A number of these nanoparticles exhibit reversible fluorescence switching [19,[56][57][58].…”

Section: Core-shell Photochromic Nanoparticlesmentioning

confidence: 99%

“…The aggregation of cyano-containing diarylethene derivative Sch. 4 in organic nanoparticles prepared by a reprecipitation method results in enhanced fluorescence and bistable photoswitching [19]. Unlike this compound, the conventional analog without the cyano-group [5] shows significant concentration fluorescence quenching in the nanoparticles.…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Core-shell Photochromic Nanoparticlesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Nanophotochromism

Barachevsky¹

2015

Organic Photonics and Photovoltaics

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“…We next investigated the relationship between these two states since optically induced switching between stable states of indole [12] and other products [17] had already been demonstrated.…”

Section: Photoactivation Of Bci Leads To Two Products Distinguished mentioning

confidence: 99%

“…This is here demonstrated for the first time for the use of the BCI precipitate in biological systems. However, the bistable photochromism of other indolyl derivatives has been recently exploited for use in digital data storage [12,17]. BCI may also potentially provide material for digital information storage.…”

Section: Introductionmentioning

confidence: 99%

Near-infrared laser illumination transforms the fluorescence absorbing X-Gal reaction product BCI into a transparent, yet brightly fluorescent substance

Matei¹,

Feng²,

Pauley³

et al. 2006

Brain Research Bulletin

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The β-galactosidase protein generated by the bacterial LacZ gene is widely used to map gene expression patterns. The ease of its use is only rivaled by green fluorescent protein, which can be used in combination with various other procedures such as immunocytochemistry, flow cytometry, or tract tracing. The β-galactosidase enzymatic reaction provides potentially a more sensitive assay of gene expression than green fluorescent protein. However, the virtual impermeability and tendency to absorb light over a wide range limit the use of the most frequently used β-galactosidase substrate, X-Gal, in combination with other fluorescent labeling procedures. Here, we provide details on a simple photoactivation procedure that transforms the light-absorbing XGal product, 5-bromo-4-chloro-3-indolyl (BCI) precipitate, into an intensely fluorescent product excited by 488 and 633 nm light. Photoactivation is achieved through exposure to 730 nm nearinfrared light emitted from a femtosecond titanium-doped Sapphire laser. Photoactivation of BCI occurs in tissue sections suspended in buffered saline, glycerol, or even embedded in epoxy resin. A protocol for the use of BCI photoactivation is here provided. Importantly, the BCI photoactivated product is photoswitchable, displaying bistable photochromism. This permits the use of the fluorescent product in a variety of co-localization studies in conjunction with other imaging modalities. As with other bistable and photoswitchable products, the BCI reaction product shows concentration quenching at high density and can be degraded by continuous exposure to intense 730 nm illumination. Therefore, care must be taken in developing imaging strategies. Our findings have implications for the use of X-Gal in gene and protein detection and provide a novel substrate for high density digital information storage.

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“…Dithienylethene (DE) [9][10][11][12] is one of the most promising candidates for photochromic materials due to its good fatigue resistance, thermal stability and an ability to undergo conformational changes between open and closed forms via photoisomerization. DE derivatives are also known to show luminescent colour changes through photoisomerization [12][13][14][15][16][17][18][19][20][21][22] . Similarly, conjugated polymers containing DE moieties in the polymer backbones exhibit photochromism attributed to structural changes of the main chains 12,[23][24][25][26] .…”

mentioning

confidence: 99%

Photochemically colour-tuneable white fluorescence illuminants consisting of conjugated polymer nanospheres

Watanabe

Hayasaka

et al. 2014

Nat Commun

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p-Conjugated aromatic polymers have attracted much interest due to their semi-conducting and luminescent properties, and are therefore regarded as promising materials for next-generation optoelectronic devices. Especially, it is considered as one of the indispensable steps for advanced function to control the optoelectronic properties by external stimuli. Herein, we show photochemically fluorescent colour-tuneable systems consisting of photoresponsive conjugated polymer nanospheres. We design and synthesize photoresponsive conjugated polymers with red, green and blue (RGB) fluorescence by introducing photoisomeric dithienylethene moieties in the side chains. A mixture of the red-, green-and blue-fluorescent polymer nanospheres exhibits photoswitchable white fluorescence between emission and quenching by irradiating external lights in both the nanosphere solution and film state. In addition, reversible change in fluorescent colour between white and RGB is also achieved by replacing a photoresponsive polymer with a non-photoresponsive analogue in the mixture. Thus, we successfully demonstrate 'photoresponsive polymer illuminant' systems bearing photochemically colour-tuneable white fluorescence.

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Photoswitchable Organic Nanoparticles and a Polymer Film Employing Multifunctional Molecules with Enhanced Fluorescence Emission and Bistable Photochromism

Cited by 482 publications

References 26 publications

Nanophotochromism

Nanophotochromism

Near-infrared laser illumination transforms the fluorescence absorbing X-Gal reaction product BCI into a transparent, yet brightly fluorescent substance

Photochemically colour-tuneable white fluorescence illuminants consisting of conjugated polymer nanospheres

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