<i>Ab initio</i> study of 3‐furyl fulgide I. Molecular structures and relative stabilities of three isomers

Yoshioka, Yasunori; Irie, Masahiro

doi:10.1002/ejtc.23

Cited by 9 publications

(10 citation statements)

References 4 publications

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“…Differently from F1E and F1Z, cyclized F1c exhibits an absorption band in the visible region, as a result of the more extended p-conjugation in this molecule. 7, 8 The positions and intensities of the absorption bands of F1E, F1Z and F1c compare well with those of similar fulgimides. 24, 25 Fig.…”

Section: Electronic Absorption Propertiessupporting

confidence: 55%

“…This phenomenon is explained by the extended p-conjugated system adopted by the photo-generated c-isomer where the cycles are forced by the closure of the new central ring to lie in a single plane. 7,8 Fulgides are closely related to fulgimides that contain a succinimide group instead of the succinic anhydride. 9 Their properties and photochemical behaviour are similar.…”

Section: Introductionmentioning

confidence: 99%

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Photochemical, photophysical and redox properties of novel fulgimide derivatives with attached 2,2′-bipyridine (bpy) and [M(bpy)3]2+ (M = Ru and Os) moieties

et al. 2009

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Fulgimides monosubstituted with [M(bpy)(3)](2+) (M = Ru, Os; bpy = 2,2'-bipyridine) chromophore units and with a single bpy group were synthesized and investigated as components of conceivable dinuclear photochromic switches of luminescence. The E-, Z- and closed-ring (C) photoisomer forms of the bpy-bound fulgimide were successfully separated by semi-preparative HPLC. The same procedure failed, however, in the case of the [M(bpy)(3)](2+)-substituted fulgimides. Energy transfer from the excited photochromic unit to the metal-bpy centre competes with the fulgimide cyclization, reducing the photocyclization quantum yields by approximately one order of magnitude compared to the non-complexed fulgimide-bpy ligand (phi(EC) = 0.17, phi(EZ) = 0.071, phi(ZE) = 0.15 at lambda(exc) = 334 nm). The cycloreversion of the fulgimide-bpy ligand is less efficient (phi(CE) = 0.047 at lambda(exc) = 520 nm). The intensity of the (3)MLCT-based luminescence of the metal-bpy chromophore (in MeCN, phi(deaer) = 6.6 x 10(-2) and tau(deaer) = 1.09 micros for Ru; phi(deaer) = 6.7 x 10(-3) and tau(deaer) = 62 ns for Os) is not affected by the fulgimide photoconversion. These results and supporting spectro-electrochemical data reveal that the lowest triplet excited states of the photochromic fulgimide moiety in all its E-, Z- and closed-ring forms lie above the lowest (3)MLCT levels of the attached ruthenium and osmium chromophores. The actual components are therefore unlikely to form a triad acting as functional switch of energy transfer from [Ru(bpy)(3)](2+) to [Os(bpy)(3)](2+) through the photochromic fulgimide bridge.

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Section: Electronic Absorption Propertiessupporting

confidence: 55%

Section: Introductionmentioning

confidence: 99%

Photochemical, photophysical and redox properties of novel fulgimide derivatives with attached 2,2′-bipyridine (bpy) and [M(bpy)3]2+ (M = Ru and Os) moieties

et al. 2009

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“…In FGs, the open form can be present in both cis and trans configurations, providing further possibilities for tuning optical properties. 24,25 In contrast to photochromism based on electrocyclisation, azobenzene (AZB) derivatives undergo a E-Z (trans-cis) isomerisation about their azo-double bond (see Fig. 1).…”

Section: Aure ´Lie Perriermentioning

confidence: 99%

Multiphotochromic molecular systems

et al. 2015

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Molecular systems encompassing more than one photochromic entity can be used to build highly functional materials, thanks to their potential multi-addressability and/or multi-response properties. Over the last decade, the synthesis and spectroscopic and kinetic characterisation as well as the modeling of a wide range of multiphotochromes have been achieved in a field that is emerging as a distinct branch of photochemistry. In this review, we provide an overview of the available multiphotochromic compounds which use a variety of photoactive building blocks, e.g., diarylethene, azobenzene, spiropyran, naphthopyran or fulgimide derivatives. Their efficiency in terms of multi-responsiveness is discussed and several strategies to circumvent the most common limitation (i.e., the loss of photochromism of one part) are described.

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“…Dithienyl perfluorocyclopentenes are an important class of thermally irreversible (P‐type) photochromic compounds, which have been extensively investigated to estimate the above‐mentioned properties and their potential application as optical switches 2, 4–7. Over the years, Irie and coworkers reported on their extensive efforts to design dual‐mode optical molecular switching materials both experimentally 2, 4, 5, 8–24 and theoretically 25–31. Lehn and coworkers 7, 32–36 have also synthesized photochromic compounds as potential molecular optical switches.…”

Section: Introductionmentioning

confidence: 99%

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

Patel

Михайлов

Belfield

et al. 2009

Int J of Quantum Chemistry

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ABSTRACT:Certain organic compounds possess the ability to change color under the influence of light, called photochromism. This change is due to ultrafast chemical transition from open to closed ring isomers (photocyclization), which can be used for optical data storage and photoswitching applications. These applications require minimization of the irreversible photodegradation of the material, called photofatigue. This property is related to the chemical rate of byproduct formation. We use density functional theory methods to predict the mechanism and activation barriers to the byproduct formation for 1,2-bis(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene in order to estimate its fatigue resistance. We also explain higher fatigue resistance for its methylated derivative. The methods used in this study may become a part of rational design strategy for the new photochromic materials.

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Ab initio study of 3‐furyl fulgide I. Molecular structures and relative stabilities of three isomers

Cited by 9 publications

References 4 publications

Photochemical, photophysical and redox properties of novel fulgimide derivatives with attached 2,2′-bipyridine (bpy) and [M(bpy)3]2+ (M = Ru and Os) moieties

Photochemical, photophysical and redox properties of novel fulgimide derivatives with attached 2,2′-bipyridine (bpy) and [M(bpy)3]2+ (M = Ru and Os) moieties

Multiphotochromic molecular systems

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

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