Tailoring Intermolecular Interactions for Efficient Room‐Temperature Phosphorescence from Purely Organic Materials in Amorphous Polymer Matrices

Kwon, Min Sang; Lee, Dong‐Wook; Seo, Sungbaek; Jung, Jaehun; J, Kim

doi:10.1002/anie.201404490

Cited by 432 publications

(260 citation statements)

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“…[1][2][3][4][5][6] Until very recently, the URTP phenomenon was mostly described for inorganic or organometallic materials containing noble metals or rare-earth elements. Among those, molecules displaying ultralong room-temperature phosphorescence (URTP) are of paramount importance notably for their applications as active materials in bioimaging, anticounterfeiting, information storage, oxygen sensing, etc.…”

Section: Thin Filmsmentioning

confidence: 99%

“…In 2017, Shoji et al revealed the exceptional phosphorescence properties of a series of simple crystalline arylboronic esters, with lifetimes up to 1.73 s, which is-to the best of our knowledge-one of the longest values ever reported for metal-free organic phosphors. [1][2][3][4][5][6] Until very recently, the URTP phenomenon was mostly described for inorganic or organometallic materials containing noble metals or rare-earth elements. After dispersion into polyvinyl alcohol (PVA) to create drop-coating thin films and long irradiation under strong UV light (65 min, 254 nm), an intense phosphorescence (Φ p up to 11.23%) associated with a long lifetime (up to 0.71 s) could be observed at room temperature in aerated atmosphere.…”

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Blue‐Light‐Absorbing Thin Films Showing Ultralong Room‐Temperature Phosphorescence

et al. 2019

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population of the excited triplet via a spinforbidden intersystem crossing from singlet to triplet. Moreover, the excited triplet can be quenched quite easily by molecular oxygen or deactivated through nonradiative pathways ( Figure 1A). In the literature, two main approaches have been developed to overcome those issues and achieve persistent RTP in aerated atmosphere. In any case, the phosphors must be contained in a rigid environment, inducing a restriction of molecular motion, be it a crystalline structure [11][12][13] or the use of an external host trapping the luminophore in the amorphous phase. [14,15] In both systems, much progress has been achieved, and efficient materials have been developed reporting long-lasting phosphorescence and high phosphorescence quantum yield. In 2017, Shoji et al. revealed the exceptional phosphorescence properties of a series of simple crystalline arylboronic esters, with lifetimes up to 1.73 s, which is-to the best of our knowledge-one of the longest values ever reported for metal-free organic phosphors. [16] Earlier this year, Su et al. designed an organic molecule that is able to participate in multiple hydrogen bondings. After dispersion into polyvinyl alcohol (PVA) to create drop-coating thin films and long irradiation under strong UV light (65 min, 254 nm), an intense phosphorescence (Φ p up to 11.23%) associated with a long lifetime (up to 0.71 s) could be observed at room temperature in aerated atmosphere. In fine, these films could be used to print and encode information. [17] These examples, as for most of the studies reporting URTP pure organic systems described in the literature, work only with excitation in the UV range to trigger the phosphorescence response. This represents a clear limitation and makes these materials hardly suitable for potential mass commercial purpose. The only exception has been reported by Huang and co-workers in 2017. [18] In this work, the authors describe the rational design of new phosphorescent organic crystalline powders, characterized by very long emission lifetimes (up to 0.84 s), due to the derivatives ability to form H aggregates. For one crystalline target with absorption strength ranging up to 450 nm, phosphorescence could be obtained after excitation with a commercial white light-emitting diode (LED). But the long-term stability of such crystalline structures is unclear and unreliable, and the elaboration of thin films from such materials can be laborious, which makes them impractical for the development of smart tags or security devices.The development of organic materials displaying ultralong room-temperature phosphorescence (URTP) is a material design-rich research field with growing interest recently, as the luminescence characteristics have started to become interesting for applications. However, the development of systems performing under aerated conditions remains a formidable challenge. Furthermore, in the vast majority of molecular examples, the respective absorption bands of the compounds are in the near ultraviolet (...

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Section: Thin Filmsmentioning

confidence: 99%

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Blue‐Light‐Absorbing Thin Films Showing Ultralong Room‐Temperature Phosphorescence

et al. 2019

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“…39,40 Furthermore, BF 2 chelates have demonstrated the ability to restrict intramolecular twisting of the aromatic-carbonyl moiety to produce rare, metal-free phosphorescence in rigid environments. 20,41–44 …”

Section: Introductionmentioning

confidence: 99%

Oxygen Sensing Difluoroboron Dinaphthoylmethane Polylactide

et al. 2015

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Dual emissive luminescence properties of solid-state difluoroboron β-diketonate-poly(lactic acid) (BF2bdk-PLA) materials have been utilized as biological oxygen sensors. Dyes with red-shifted absorption and emission are important for multiplexing and in vivo imaging, thus hydroxyl-functionalized dinaphthoylmethane initiators and dye-PLA conjugates BF2dnm(X)PLA (X = H, Br, I) with extended conjugation were synthesized. The luminescent materials show red-shifted absorbance (~435 nm) and fluorescence tunability by molecular weight. Fluorescence colors range from yellow (~530 nm) in 10 – 12 kDa polymers to green (~490 nm) in 20 – 30 kDa polymers. Room-temperature phosphorescence (RTP) and thermally activated delayed fluorescence (TADF) are present under a nitrogen atmosphere. For the iodine-substituted derivative, BF2dnm(I)PLA, clearly distinguishable fluorescence (green) and phosphorescence (orange) peaks are present, making it ideal for ratiometric oxygen-sensing and imaging. Bromide and hydrogen analogues with weaker relative phosphorescence intensities and longer phosphorescence lifetimes can be used as highly sensitive, concentration independent, lifetime-based oxygen sensors or for gated emission detection. BF2dnm(I)PLA nanoparticles were taken up by T41 mouse mammary cells and successfully demonstrated differences in vitro ratiometric measurement of oxygen.

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“…The unique properties could be concentrated on ap ure organic compound through this design strategy,w hichprovides an ew efficient channel for the discovery of efficient mechanoresponsive organic materials.Controlling and tuning the solid-state luminescence of organic materials continues to be an attractive topic in both theoretical research and practical applications in the fields of sensing, [1] color displays, [2] and data storage. Following the principle of color mixing, myriad emission colors with aw ide range from orange to purple and across white zone in astraight line in the chromaticity diagram of the Commission Internationale de lEclairage (CIE) can be obtained by simply mechanical grinding the compound.…”

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confidence: 99%

“…Controlling and tuning the solid-state luminescence of organic materials continues to be an attractive topic in both theoretical research and practical applications in the fields of sensing, [1] color displays, [2] and data storage. [3] Ther elationship in the molecular level between the emission properties of organic luminescent materials and the external pressure or mechanical stimuli has recently gained considerable attention because the knowledge of such ar elationship is essential to real-world applications of the "smart" materials.…”

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confidence: 99%

Linearly Tunable Emission Colors Obtained from a Fluorescent–Phosphorescent Dual‐Emission Compound by Mechanical Stimuli

Mao

Yang

Mu³

et al. 2015

Angewandte Chemie

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Organic mechanoluminochromic materials are mechano/piezo-responsive and promising for applications in sensors,d isplays,a nd data storage devices.H owever,t heir switching range of emission is seriously impeded by only one kind of emission (either afluorescent or phosphorescent peak) in the spectrum of single organic compounds.T his study presents ad esign strategy for pure organic compounds with excellent room-temperature fluorescent-phosphorescent dualemission (rFPDE) properties,w hich combines the effective factors of dipenylsulfone group,c rystalline state,a nd heavy atom effect. Following the principle of color mixing, myriad emission colors with aw ide range from orange to purple and across white zone in astraight line in the chromaticity diagram of the Commission Internationale de lEclairage (CIE) can be obtained by simply mechanical grinding the compound. The unique properties could be concentrated on ap ure organic compound through this design strategy,w hichprovides an ew efficient channel for the discovery of efficient mechanoresponsive organic materials.Controlling and tuning the solid-state luminescence of organic materials continues to be an attractive topic in both theoretical research and practical applications in the fields of sensing, [1] color displays, [2] and data storage. [3] Ther elationship in the molecular level between the emission properties of organic luminescent materials and the external pressure or mechanical stimuli has recently gained considerable attention because the knowledge of such ar elationship is essential to real-world applications of the "smart" materials. [4][5][6][7][8][9][10][11] Many studies have been conducted on mechano/piezo-responsive organic luminescent materials,a lso known as mechanoluminochromic materials.H owever,s tudies focusing on the switching range of the emission of such materials remain limited. [11,12] On the other hand, although the compounds are constructed with complex molecular structures,t hese single organic compounds generally exhibit only one kind of emission, either fluorescent or phosphorescent, in the solid state. [13] This limitation seriously impedes the extent of the switching range of such compounds.T hus,p ure organic molecules with room-temperature fluorescent-phosphorescent dual-emission (rFPDE) properties are essentially superior to the above-mentioned luminophores for mechanoluminochromic materials.G iven the difference between the radiative processes of fluorescence and phosphorescence,the separate dual emissions in rFPDE materials exhibit respectively tunable luminescent characteristics under external stimuli, [14] which significantly enrich their emission switching. We present in this communication as uccessful strategy to obtain new rFPDE materials with al arge separation in their dual emissions from asingle organic compound ( Figure 1A). When the crystals of the rFPDE organic compound were converted into the amorphous powder by mechanical stimulus,the compound exhibits an unusually wide range of blue shift in its emission fr...

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Tailoring Intermolecular Interactions for Efficient Room‐Temperature Phosphorescence from Purely Organic Materials in Amorphous Polymer Matrices

Cited by 432 publications

References 22 publications

Blue‐Light‐Absorbing Thin Films Showing Ultralong Room‐Temperature Phosphorescence

Blue‐Light‐Absorbing Thin Films Showing Ultralong Room‐Temperature Phosphorescence

Oxygen Sensing Difluoroboron Dinaphthoylmethane Polylactide

Linearly Tunable Emission Colors Obtained from a Fluorescent–Phosphorescent Dual‐Emission Compound by Mechanical Stimuli

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