Spiropyrans

Bertelson, Robert C.

doi:10.1007/0-306-46911-1_2

Cited by 64 publications

(74 citation statements)

References 164 publications

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“…The direct interconversion between the two states SP and ME relies on the photoisomerization of a spiropyran chromophore (36)(37)(38)(39)(40)(41). This switching process is controlled solely by optical inputs, and the two isomers have distinct absorption properties in the visible region (32).…”

Section: Resultsmentioning

confidence: 99%

All-optical processing with molecular switches

Raymo

Giordani

2002

Proc. Natl. Acad. Sci. U.S.A.

196

100

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A gradual transition from electrical to optical networks is accompanying the rapid progress of telecommunication technology. The urge for enhanced transmission capacity and speed is dictating this trend. In fact, large volumes of data encoded on optical signals can be transported rapidly over long distances. Their propagation along specific routes across a communication network is ensured by a combination of optical fibers and optoelectronic switches. It is becoming apparent, however, that the interplay between the routing electrical stimulations and the traveling optical signals will not be able to support the terabit-per-second capacities that will be needed in the near future. O ptical communication networks transport hundreds of gigabits per second over hundreds of kilometers (1, 2). The efficient transmission of data relies on the integration of optoelectronic devices and optical fibers. They are responsible for the generation, amplification, conduction, routing, and detection of optical signals. At each step, the continuous interplay between optical and electrical stimulations controls data processing. In particular, electronically controlled switches guide the traveling optical signals along programmed routes across the communication networks. Signal routing requires multiple optoelectronic and electroopitc conversion steps. From input fibers, the propagating optical signals reach the routing devices, where they are converted into electrical signals, processed in this form, reconverted into optical signals and, finally, directed to specific output fibers. These inevitable optoelectronic and electroopitc conversions are a major ''bottleneck'' to the development of optical networks (3, 4). Besides the obvious loss in signal intensity associated with each conversion step, these switching devices are relatively slow and can process only few signals simultaneously. Only a tiny fraction of the potential transmission capacity of optical fibers is used in present communication networks. These limitations are stimulating considerable research efforts to develop innovative operating principles for optical switching (5-8).A variety of clever and efficient strategies to completely eliminate undesired optoelectronic and electroopitc conversion steps have already been identified (5-8). It is now possible to maintain the propagating signals exclusively at the optical level. However, these methods rely heavily on electronics and, presumably, they will not be able to support the terabit-per-second capacities that will be needed in the near future. Their major limitation is that the switching operations are still controlled by electrical stimulations. The traveling optical signals are routed in response to electrical signals, which cannot handle the immense parallelism offered by optical fibers. Strategies to control optical signals in response to optical signals are potentially much more attractive. However, the identification of reliable operating principles for all-optical switches is a challenging goal.Molecular switch...

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Section: Resultsmentioning

confidence: 99%

All-optical processing with molecular switches

Raymo

Giordani

2002

Proc. Natl. Acad. Sci. U.S.A.

196

100

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“…We found that the cyclic forms of the SPP at 293 K do not possess fluorescence. The maxima of the long-wavelength bands of the acyclic merocyanine isomers B of spiropyrans 1-4 lie in the range 540-586 nm, which corresponds to the absorption data of merocyanine isomers of previously described spiropyrans (Table 1) [2,3].…”

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confidence: 98%

“…The mechanism for the photochromic transformation of spiropyrans, spirooxazines, and their salts (Scheme 2) involves the thermally and photochemically reversible heterolytic clevage of the C spiro -O bond of cyclic isomer A with subsequent cis-trans isomerization to give metastable merocyanine form B, which converts to the starting spiroform either spontaneously or by the action of visible light [2,3].…”

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confidence: 99%

Photo- and thermochromic spiranes. 31.* Photochromic cationic spiropyrans with a pyridinium fragment in the aliphatic side chain*2

Voloshin

Bezugliy

Соловьева

et al. 2008

Chem Heterocycl Comp

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Syntheses are reported for cationic indoline spiropyrans with a quaternized pyridinium fragment in the aliphatic side chain, which display photochromic properties in solution. The major effect of introducing a quaternized pyridinium fragment into the benzopyran part of the spiropyran entails a significant decrease in the rate of thermal relaxation processes.Keywords: cationic indolinospiropyrans, pyridinium fragment, photochromism, electronic absorption spectroscopy.Photochromic organic molecules, some of which are spiropyrans and spirooxazines, have recently been the subject of intensive research due to the use of these compounds in optical recording and data transformation systems, sensors, optical electronics, optical bioelectronics, and transport systems [2-5].However, the limit to improving the characteristics of monofunctional materials has now been reached and attention is being directed toward the development of hybrid polyfunctional materials holding promise for application in molecular electronics.A possible solution of this problem lies in the creation of hybrid polyfunctional materials, which combine structural units responsible for different physicochemical properties such as photochromism and magnetism [6][7][8][9], photochromism and conductivity [10,11], electrical and magnetic properties [12], and optical dichroism and magnetism [13]. A systematic study of both the structure and properties of such units and the feasibility of their combination into a single crystal lattice is required for the development of such materials from molecular units differing in their chemical nature, the investigation of the interaction of such units on each other, and methods for the modification of the properties of the separate units to impart desired properties to the hybrid materials. _______ * For Communication 30 see [1]. * 2 Dedicated to Academician of the Russian Academy of Sciences B. A. Trofimov on his 70th jubilee. __________________________________________________________________________________________

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“…[23,24,29] The use of photochromic compounds in the context of cucurbituril chemistry has been rarely investigated. Recently, the partial inclusion of a spiropyran photochrome [30,31] in cucurbit[n]urils (n = 7 and 8, CB7 and CB8, respectively) was reported. [32,33] On the one hand, it was shown that CB8…”

Section: Introductionmentioning

confidence: 99%

Switching Properties of a Spiropyran–Cucurbit[7]uril Supramolecular Assembly: Usefulness of the Anchor Approach

Nilsson

Carvalho

et al. 2012

ChemPhysChem

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A nitrospiropyran, which was modified with a cadaverine-derived anchor, was investigated with respect to its thermally-induced isomerizations, hydrolytic stability of the merocyanine form, and the photochromic ring closure. The host-guest complexation of the anchor by the cucurbit [7]uril macrocycle, evidenced by absorption titration, NMR spectroscopy, and electrospray ionization mass spectrometry, produced significant improvements of the switching properties of the photochrome: a) a ca. 70 times faster appearance of the merocyanine form, b) a practically unlimited hydrolytic stability of the merocyanine (two and a half days without any measureable decay), and c) a fast, clean, and fatigueresistant photoinduced ring-closure back to the spiro form. The importance of an adequate molecular design of the anchor was demonstrated by including control experiments with spiropyrans with a shorter linker or without such structural asset.

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Spiropyrans

Cited by 64 publications

References 164 publications

All-optical processing with molecular switches

All-optical processing with molecular switches

Photo- and thermochromic spiranes. 31.* Photochromic cationic spiropyrans with a pyridinium fragment in the aliphatic side chain*2

Switching Properties of a Spiropyran–Cucurbit[7]uril Supramolecular Assembly: Usefulness of the Anchor Approach

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