Theoretical study of photochromic compounds, part 2: Thermal mechanism for byproduct formation and fatigue resistance of diarylethenes used as data storage materials

Patel, Pansy D.; Михайлов, И. В.; Belfield, Kevin D.; Masunov, Artëm E.

doi:10.1002/qua.22358

Cited by 66 publications

(55 citation statements)

References 70 publications

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“…For each DTE, the absorbance was monitored at the λ max of the ringclosed isomer. [31][32][33][34] Further, the formation of photostable byproducts in DTEs has been proposed to involve a methylcyclopentene diradical as a possible intermediate. These results suggest that the presence of phenylethynyl substituents in DTEs (i.e., 1 and 2) decreases their photostability relative to the presence of a methyl group, as in 3.…”

Section: Synthesis Of Asymmetrical Amphiphilic Dtesmentioning

confidence: 99%

Photocontrol of ion permeation in lipid vesicles with amphiphilic dithienylethenes

et al. 2015

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The integration of photochromic dithienylethenes (DTEs) with lipid vesicles as photoresponsive membrane disruptors for ion transport applications has been examined. We have synthesized three amphiphilic DTEs 1-3 that incorporate a terminally charged alkyl chain, and contain methyl or phenylethynyl substituents at the reactive carbons. Our photochromic reactivity studies suggest that the inclusion of a single alkyl chain favors the photoactive antiparallel conformation of DTEs, given the significant improvement in the cyclization quantum yield over previous phenylethynyl derivatives. Our ion permeation studies show that the open-ring isomers of these DTEs are more disruptive than the closed-ring isomers in the four lipid vesicle systems studied, regardless of their lamellar phase at room temperature. In addition, a steric effect was clearly observed as DTEs incorporating the comparatively smaller methyl group exhibited lower rates of ion permeation than the bulkier phenylethynyl group. In all cases, UV irradiation led to a reduction in ion permeability. In fact, the methyl analog exhibited a significant reduction in ion permeability in gel-phase lipid vesicles upon UV exposure. Also, the hexyl chain derivatives had a greater effect on membrane permeability than the dodecyl derivative owing to their relative position in the bilayer membrane of lipid vesicles.

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Section: Synthesis Of Asymmetrical Amphiphilic Dtesmentioning

confidence: 99%

Photocontrol of ion permeation in lipid vesicles with amphiphilic dithienylethenes

et al. 2015

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“…Therefore, the nonswitchable character in basic medium is not related to an unfavorable orbital disposition but is probably due to the creation of nonphotochromic by-products. This problem, related to a diatropic rearrangement, has already been discussed elsewhere [13,42], and is not the focus of the present work.…”

Section: In All Its Formsmentioning

confidence: 92%

Ab initio modeling of optical spectra in pH‐sensitive diarylethenes

Maurel

Perrier

Jacquemin

2011

Int J of Quantum Chemistry

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ABSTRACT:The photochromic and acidochromic shifts undergone by recently synthesized diarylethene photochromes have been simulated using a Time-Dependent Density Functional Theory approach relying on a range-separated functional, namely CAM-B3LYP. The selected approach is generally accurate for reproducing the variations of the spectral features, though acidochromic shifts are clearly more challenging than their photochromic counterparts. More importantly, an analyzis of the shapes of the relevant molecular orbitals grants insights into the electro-cyclization of several diarylethenes, therefore partly allowing to understand the presence of experimental deadlocks.

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“…In particular, we focus on molecular materials, and, thereby, topics of devices, for example, laser system, optical system, and so on, which have been introduced in some excellent reviews [2,34], are not included. The significant studies on theory and calculations mainly using a DFT (density functional theory) method, which are useful in the design of new two-photon absorbing molecules, have also been reported [35][36][37] and reviewed [38]. …”

Section: Methodsmentioning

confidence: 99%

Two-Photon Absorbing Molecules as Potential Materials for 3D Optical Memory

Ogawa

2014

Applied Sciences

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Abstract:In this review, recent advances in two-photon absorbing photochromic molecules, as potential materials for 3D optical memory, are presented. The investigations introduced in this review indicate that 3D data storage processing at the molecular level is possible. As 3D memory using two-photon absorption allows advantages over existing systems, the use of two-photon absorbing photochromic molecules is preferable. Although there are some photochromic molecules with good properties for memory, in most cases, the two-photon absorption efficiency is not high. Photochromic molecules with high two-photon absorption efficiency are desired. Recently, molecules having much larger two-photon absorption cross sections over 10,000 GM (GM= 10 ) have been discovered and are expected to open the way to realize two-photon absorption 3D data storage.

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Theoretical study of photochromic compounds, part 2: Thermal mechanism for byproduct formation and fatigue resistance of diarylethenes used as data storage materials

Cited by 66 publications

References 70 publications

Photocontrol of ion permeation in lipid vesicles with amphiphilic dithienylethenes

Photocontrol of ion permeation in lipid vesicles with amphiphilic dithienylethenes

Ab initio modeling of optical spectra in pH‐sensitive diarylethenes

Two-Photon Absorbing Molecules as Potential Materials for 3D Optical Memory

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