Determination of reaction quantum yields of photochromic fulgides using mid-IR spectroscopy: quantitative evaluation and normal mode analysis

Seibold, Marc; Port, H.; Gustav, Klaus

doi:10.1016/s0009-2614(99)01134-3

Cited by 18 publications

(13 citation statements)

References 18 publications

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“…1) and fulgide 4a also undergo coloration upon ultraviolet irradiation. 9,10 Indeed, the photoinduced closing of a six-membered ring at the core of their structures results in the formation of the colored isomers 3b and 4b, respectively. These compounds, however, are thermally stable and revert to the original and colorless forms only after visible irradiation.…”

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confidence: 99%

“…The visible absorbance changes that accompany the photoinduced conversion of 1a-4a into 1b-4b are a consequence of the pronounced stereoelectronic modifications associated with these transformations. [7][8][9] In fact, these photochromic processes affect a diversity of structural and electronic properties at the molecular level in addition to the absorption signature. For example, the trans isomer 1a switches to the cis form 1b with a decrease of ca.…”

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Fluorescence modulation with photochromic switches in nanostructured constructs

2009

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This tutorial review illustrates the structural design, photochemical and photophysical properties of nanostructured constructs incorporating luminescent and photochromic components. In these systems, the pronounced structural and electronic modifications that accompany the transformations of the photochromic components can be exploited to modulate the emission intensity of the luminescent components on the basis of electron and energy transfer processes. These photoresponsive systems can be assembled by: (1) integrating fluorescent and photochromic components within the main chain of the same polymer; (2) attaching multiple photochromes to a fluorescent organic polymer or luminescent inorganic nanoparticle; (3) appending either independent fluorophores and photochromes or fluorophore-photochrome dyads to a common polymer scaffold; (4) trapping distinct fluorophores and photochromes within the hydrophobic interior of the same cross-linked polymer. In all instances, the changes in absorbance and/or redox potentials associated with the reversible interconversion of the two states of each photochromic component regulate the radiative deactivation of the luminescent components. As a result, the emission intensity of these nanoscaled assemblies can reversibly be switched between high and low values under the influence of optical stimulations. Thus, these clever operating principles for fluorescence modulation can lead to the development of innovative functional and nanostructured materials with photoresponsive character. In particular, protocols for the optical writing and reading of data as well as luminescent probes for bioimaging applications might ultimately emerge from these fundamental studies on photoresponsive molecular switches.

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Fluorescence modulation with photochromic switches in nanostructured constructs

2009

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“…Other common photochromic compounds based on ring opening and closing steps are the dihydroazulenes (e.g., 3a in Figure 1), [13] the spiroindolizines (e.g., 4a), [14,15] the dihydropyrans (e.g., 5a) [16] and the fulgides (e.g., 6a). [17] In alternative to ring opening and closing reactions, photoinduced cis/trans isomerizations can also be exploited to implement photochromic transformations. For example, the colorless trans-azobenzene 7a switches to the colored cis isomer 7b upon ultraviolet irradiation with a quantum yield of 0.1 in cyclohexane.…”

Section: Photochromic Compoundsmentioning

confidence: 99%

Fluorescent Switches Based on Photochromic Compounds

2009

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The photochemical transformations associated with photochromic compounds can be exploited to switch the emission of complementary fluorophores under the influence of optical stimulations. Specifically, fluorescent and photochromic components can be integrated within the same molecular or supramolecular assembly and the significant changes in the stereoelectronic properties associated with the photoinduced interconversion of one component can be designed to modulate the emission intensity and/or wavelength of the other. In particular, the modifications in absorption properties, conjugation, dipole moment, redox potentials and shape of a photochrome can all be transduced effectively into reversible alterations of the emissive behavior of a fluorophore. Furthermore, some of these ingenious mechanisms for fluorescence 1. Photochromism History and DefinitionsThe term "photochromism" was introduced in the early 1950s to indicate the photoinduced and reversible change in color of certain compounds.[1] Since then, the number of publications on photochromism has increased exponentially [a]

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“…Upon photoirradiation, photochromic compounds reversibly change not only the absorption spectra but also other physicochemical properties, such as refractive index, electrical moment dielectric constants, chelate formation, ion dissociation, oxidation/reduction potentials, and phase transitions during the photochromic reaction. Fulgides, a kind of photochromic systems, which have attracted extent interesting and lots of papers, are reported on synthesis, properties, and potential photoelectronic applications [10, 11] because of the fatigue resistance and thermally irreversibility. However, among them,there are few publications that contribute to holographic recording.…”

Section: Introductionmentioning

confidence: 99%

Improved photochromic and fatigue performance of (E)‐dicyclopropylmethylene‐(2,5‐dimethyl‐3‐furylethylidene)‐succinicanhydride doped in polyurethane thin film

Asiri

2011

Polymer Engineering & Sci

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Improved photochromic properties and fatigue performance of (E)‐dicyclopropylmethylene‐(2,5‐dimethyl‐3‐furylethylidene)‐succinicanhydride doped in polyurethane thin film were discussed in this study. Fulgide 1‐E doped in polyurethane polymer films was heated at various annealing temperatures. Upon irradiation with UV light (366 nm), fulgide 1‐E undergoes a conrotatory ring closure to the pink‐colored closed form 1‐C. The latter color was switched back to the original color when the films were irradiated with white light. The kinetics of photocoloration and photobleaching processes was followed spectrophotometrically by monitoring the absorbance of the ring‐closed product 1‐C at its λmax of 525 nm. The first‐order plots of photocoloration reaction show distinct linear line and the slope of which corresponding to the first‐order rate constants k. It was found that for photocoloration reaction, the rate constant of the photocoloration reaction is slower than the photobleaching reaction, and both reactions decrease with increasing the annealing temperatures. It was found that there was almost complete loss of photochemical fatigue resistance of fulgide 1 doped in polyurethane polymer film irrespective of the annealing temperature. POLYM. ENG. SCI., 2012. © 2011 Society of Plastics Engineers

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Determination of reaction quantum yields of photochromic fulgides using mid-IR spectroscopy: quantitative evaluation and normal mode analysis

Cited by 18 publications

References 18 publications

Fluorescence modulation with photochromic switches in nanostructured constructs

Fluorescence modulation with photochromic switches in nanostructured constructs

Fluorescent Switches Based on Photochromic Compounds

Improved photochromic and fatigue performance of (E)‐dicyclopropylmethylene‐(2,5‐dimethyl‐3‐furylethylidene)‐succinicanhydride doped in polyurethane thin film

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