High-Contrast Electroswitching of Emission and Coloration Based on Single-Molecular Fluoran Derivatives

Kanazawa, Kenji; Nakamura, Kazuki; Kobayashi, Norihisa

doi:10.1021/jp5060588

Cited by 36 publications

(20 citation statements)

References 64 publications

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“…In general, fluoran derivatives used as thermochromic dyes are normally transparent because central carbon of spirostructure linking xanthene and lactone unit through sp 3 hybrid orbitals breaks conjugation length, resulting in a large bandgap. On the other hand, when the fluoran derivative is oxidized and the lactone ring is opened, the conjugation length becomes longer as the sp 3 hybrid orbital of central carbon is converted to sp 2 hybrid orbital, which reduces the bandgap and shifts absorption wavelength to red region . The absorption wavelength of fluoran dyes can be tuned by the substituents linked to the xanthene unit, and some fluoran derivatives that are black in the lactone ring‐open state have been reported .…”

Section: Resultsmentioning

confidence: 99%

High‐Performance Electrochromic Optical Shutter Based on Fluoran Dye for Visibility Enhancement of Augmented Reality Display

Kim

et al. 2018

Advanced Optical Materials

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In this paper, a high‐performance electrochromic optical shutter (ECOS) based on fluoran dye and an augmented reality (AR) display system comprising of ECOS are proposed. The electrochromic reactions of the fluoran dye that transmit or absorb visible light depending on its redox state are activated by the protons generated from hydroquinone derivatives, thereby significantly improved visible light absorption and decreased driving voltage. The visible light‐absorbing function of ECOS is a sole solution for overcoming the main issue of low visibility of displayed images under strong ambient light conditions in optical see‐through head‐mounted displays (OST‐HMDs) implementing augmented reality. The proposed AR display effectively solves the problem by significantly increasing the ambient contrast ratio and color gamut of the displayed image on OST‐HMD even in the strong ambient light condition due to the excellent visible light‐absorbing function of ECOS.

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Section: Resultsmentioning

confidence: 99%

High‐Performance Electrochromic Optical Shutter Based on Fluoran Dye for Visibility Enhancement of Augmented Reality Display

Kim

et al. 2018

Advanced Optical Materials

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“…Recently, many electrofluorochromic materials have been prepared and used in photoelectric conversion devices, biological information storage, chemical sensors, and intelligent displays . So far, electrofluorochromic materials can be broadly divided into four types: molecular dyads, intrinsically switchable fluorophores, switchable fluorescent polymers, and switchable fluorescent composites . Among those, electrofluorochromic polymers are highly desirable for their fast switching speed, facile molecular design and good processability.…”

Section: Methodsmentioning

confidence: 99%

New electrofluorochromic polymer bearing oligoaniline, carbazole, and polyhedral oligomeric silsesquioxane: Synthesis and properties

Yan

Jia

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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Electrofluorochromic materials have gained much exposure in recent years due to their reversible switching of fluorescence intensity upon electrical potentials. 1 The electrofluorochromic property can be generated from the interplay between electroactive moiety and fluorescence emission moiety. Recently, many electrofluorochromic materials have been prepared and used in photoelectric conversion devices, biological information storage, chemical sensors, and intelligent displays. 2,3 So far, electrofluorochromic materials can be broadly divided into four types: molecular dyads, 4-6 intrinsically switchable fluorophores, 7-9 switchable fluorescent polymers, [10][11][12][13][14][15][16] and switchable fluorescent composites. [17][18][19][20][21][22] Among those, electrofluorochromic polymers are highly desirable for their fast switching speed, facile molecular design and good processability. There are currently a variety of strategies to construct the electrofluorochromic polymers using different electroactive units and fluorescence emission units. For example, Xu and coworkers designed and synthesized a novel alternating conjugated polymer based on thiophene and tetraphenylethene derivatives, which exhibited an aggregation-enhanced fluorescent emission, electrochromic, and electrofluorochromic dualswitching behavior. 10 Kawabata and Goto reported a series of fluorescent conjugated polymers through electrochemical polymerization. The resultant polymer nanofibers showed an interesting electrofluorochromic performance in polarized photoluminescence. 23 Fluorescent polytriphenylamines was also prepared and reported as electroflorochromic materials. [24][25][26][27][28][29] Approving electrofluorochromic performance was displayed, ascribing to effective mitigation of aggregation-caused quenching effect benefiting from unique propeller starburst structure of triphenylamine. For better understanding of electrofluorochromic mechanism and expansion of practical applicability, electrofluorochromic polymers need to be further explored.As the model compounds of polyaniline, oligoanilines have drawn much attention in recent years due to their well-defined structure, good electro-optical properties, and facile molecular design. In light of their reversible electroactivity and relatively low redox potentials, oligoanilines have also been employed as electroactive moiety to construct electrofluorochromic polymers coupled with fluorescent triphenylamine derivatives. 30,31 Expected electrofluorochromic behavior has been revealed through several of electrochemical measurements with the assistance of spectrometric techniques. Due to the coexistence of two types of electroactive moieties (oligoaniline and triphenylamine), the energy transfer could between each other, resulting in an unclear electrofluorochromic mechanism for these system.In this work, we designed and synthesized a new electroactive polymer bearing oligoaniline, carbazole, and polyhedral oligomeric silsesquioxane (POSS) pendants (POCP). Its electrochemical properties, i...

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“…In this case, therefore, the electroswitching from a nonfluorescent to a fluorescent species occurs because there is a change in the molecular structure of the fluoran molecule. [ 60,61 ] The other example of fluorescence enhancing has been reported by our group who proposed the use of liquid crystalline thienoviologens as ISF. [ 30,62 ] In such a case, the thienoviologen dication is a highly emissive species but, on reduction to the radical cation species, an increase of the fluorescence occurs, accompanied by a shift of the emission maximum, due to a change in the supramolecular organization of the thienoviologens in the liquid crystalline phase.…”

Section: Fundamentals Of Electrofluorochromismmentioning

confidence: 99%

Overview on the Recent Progress on Electrofluorochromic Materials and Devices: A Critical Synopsis

Corrente

Beneduci

2020

Advanced Optical Materials

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case of electroluminochromism (ELC), which includes tuning of the phosphorescence. This is mainly observed in metal organic complexes based on metals with d 6 , d 8 , and d 10 configuration such as Ir III , Ru II , and Eu III that, in contrast to entirely organic systems, exhibit emission lifetimes of several seconds. [19,20] Metal complexes generally have also rich excited state properties, good redox reversibility, high emission quantum yields, thereby showing electroluminochromic response with multicolor tunable emission in a wide wavelength range. [19,20] This interesting class of ELC materials has been extensively discussed in a some very recent reviews [19,20,21] to which the reader is reminded. EFC technology is highly desirable in electro-optic applications [8-10] as well as in fluorescent imaging. [22-24] For most of the above applications, EFC materials and devices should possess ideal properties such as high contrast of optical response, rapid switching time, long-term stability,

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High-Contrast Electroswitching of Emission and Coloration Based on Single-Molecular Fluoran Derivatives

Cited by 36 publications

References 64 publications

High‐Performance Electrochromic Optical Shutter Based on Fluoran Dye for Visibility Enhancement of Augmented Reality Display

High‐Performance Electrochromic Optical Shutter Based on Fluoran Dye for Visibility Enhancement of Augmented Reality Display

New electrofluorochromic polymer bearing oligoaniline, carbazole, and polyhedral oligomeric silsesquioxane: Synthesis and properties

Overview on the Recent Progress on Electrofluorochromic Materials and Devices: A Critical Synopsis

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