Photochromic reactions of crystalline spiropyrans and spirooxazines induced by intense femtosecond laser excitationDedicated to Professor Frank Wilkinson on the occasion of his retirement.

Suzuki, Mototsugu; Asahi, Tsuyoshi; Masuhara, Hiroshi

doi:10.1039/b108108j

Cited by 58 publications

(38 citation statements)

References 60 publications

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“…Using this principle, FP resonators have recently been used in fiber for sensing applications. [15][16][17] A drawback to using SPO is that the photochromic reaction is slow in polymer blends and is prohibited in crystal form 18 as the conformation change is impeded by the solid phase. Therefore, we combine the SPO liquid solution with optical fibers.…”

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confidence: 99%

Spiro-oxazine photochromic fiber optical switch

Huang

Liang

Poon

et al. 2006

Applied Physics Letters

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A photochromic all-optical switch in telecommunication-grade fiber is fabricated by filling a fiber Bragg grating Fabry-Pérot resonator with a spiro-oxazine solution. The narrow linewidth of the resonator allows for a high sensitivity of the resonance wavelengths to the index change. The switch is controlled by low intensity UV light exposure, and operation at infrared telecommunication wavelengths is demonstrated. The switching speed on the order of minutes has been achieved.

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confidence: 99%

Spiro-oxazine photochromic fiber optical switch

Huang

Liang

Poon

et al. 2006

Applied Physics Letters

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“…15 An interesting effect is the formation of the short lived (characteristic lifetime about several nanoseconds) isomers of the nonplanar photocol ored form upon irradiation with femtosecond laser pulses of microcrystalline powders of the spiro compounds that exhibit no photochromic properties under the conditions of steady state irradiation. [16][17][18][19] In this work, the photochromic transformations of phenanthroline annulated 3,3 trimethylspiro[indoline 2,2´ bipyrido [3,2 f] [2,3 h] [1,4]benzoxazine] (SPO1) 20 in the polycrystalline state (see Scheme 1) were found and studied.…”

Section: Methodsmentioning

confidence: 99%

“…37 The character istic lifetime of the nonplanar cisoid isomers formed upon the photoexcitation of spiropyrans and spirooxazines is several nanoseconds in the polycrystalline state. [16][17][18] The broad distribution of molecules of the B form over planar transoid isomeric forms appears as a result of local melting of a microcrystal of SPO1 under the action of a laser pulse. The effect of nonequilibrium distribution over isomeric forms is manifested in the transient absorp tion spectra and kinetics of formation of the absorption of the В form in experiments on laser flash photolysis (see Figs 1 and 5).…”

Section: Kinetics Of Thermal Relaxation Of the B Formmentioning

confidence: 99%

Photochromic properties of phenanthroline-annulated spirooxazine in the solid state

et al. 2011

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Photochromic transformations of phenanthroline annulated spirooxazine were observed in polycrystalline powders and solid phase films obtained from solutions by solvent evaporation. The spectral and kinetic properties of the solid phase films were studied by stationary absorp tion spectroscopy and laser flash photolysis. The mechanism of photoinitiated reactions of solid phase samples of phenanthroline annulated spirooxazine includes mutual transforma tions of different transoid isomers of the merocyanine form.Organic photochromic compounds can be used in the development of various photosensitive systems, such as optical media with nonlinear absorption, systems of opti cal information recording, and optical switchers. Com pounds retaining ability to photochromic transformations in solid films or in the crystalline state are of special inter est. Such compounds are actively used during the recent decade (see reviews 1,2 and references therein). Photo chromic transformations were observed in both poly crystalline films and single crystals of diarylethenes 3,4 and derivatives of salicylaldehyde, 1,5 arylhydrazides, 6 fulgides, 7 and chromenes. 8 Scheme 1Spiropyrans and spirooxazines (Scheme 1) refer to the most widely studied classes of photochromic compounds. In this case, photochromic transformations are due to tran sitions between the closed spiro form А and open mero cyanine form В. As a rule, spiropyrans and spirooxazines are not photochemically active in microcrystalline pow ders and single crystals. 9 This is explained by the fact that the phototransformations caused by bond cleavage between the spiro carbon atom and oxygen atom followed by isomerization of the molecule require large free volume.However, several examples for the manifestation of the ability of spiropyrans and spirooxazines to photochromic transformations in the poly and monocrystalline states are described in the literature. These properties are char acteristic of crystals of spiropyran 9-11 and spirooxazine 12 salts including pyridinium moiety. In this case, the possi bility of photoisomerization is determined, most likely, by the specific feature of the structures of these compounds in the solid state. The crystal structure formed by cationic layers separated by particular iodide ions provides a suffi cient volume for phototransformations. Several examples are known for the non salt spiro compounds exhibiting photochromic transformations. The photochromic prop erties of single crystals of N (n propyl)nitrospiropyran were observed. 13 The photochromic transformations of spirooxazine containing the azahomoadamantyl group were reported. 14 The free volume necessary for photo isomerization is provided by either cavities in the crystal packing 13 or a large size of one of the functional groups. 14

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“…4). All isomers of the open form can rapidly interconvert and are assumed to be in equilibrium [38]. The open forms with the exception of the z-cis form are grouped together and coded as A for the following analysis.…”

Section: Methodsmentioning

confidence: 99%

Tuning the Thermal Relaxation of a Photochromic Dye in Functionalized Mesoporous Silica

Mühlstein

Sauer²,

Bein

2009

Adv Funct Materials

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In this study, it is shown that the kinetics of the back‐switching reaction of a photochromic spirooxazine dye encapsulated in mesoporous silica materials can be significantly influenced both by the space available to the dye molecules and by the functionalization of the silica wall. Steric hindrance of the ring‐closing process due to high dye content or small pore size leads to a slow fading speed of the irradiated dye species. Further, the density of surface silanol‐groups present at the silica walls has an effect on the switching behavior of the dye because of their ability to stabilize the zwitterionic merocyanine isomers, thereby slowing the fading process from the open to the closed form. This stabilization effect is further enhanced in the presence of acidic functional groups, while, in contrast, basic functional groups reduce the stabilization of the open‐from dye isomers, and thus a faster decay of the irradiated species is observed. Control over the fading speed of photochromic dyes is interesting for applications requiring a particularly fast or slow fading speed.

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Photochromic reactions of crystalline spiropyrans and spirooxazines induced by intense femtosecond laser excitationDedicated to Professor Frank Wilkinson on the occasion of his retirement.

Cited by 58 publications

References 60 publications

Spiro-oxazine photochromic fiber optical switch

Spiro-oxazine photochromic fiber optical switch

Photochromic properties of phenanthroline-annulated spirooxazine in the solid state

Tuning the Thermal Relaxation of a Photochromic Dye in Functionalized Mesoporous Silica

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