Unveiling a New Aspect of Simple Arylboronic Esters: Long-Lived Room-Temperature Phosphorescence from Heavy-Atom-Free Molecules

Shoji, Yoshiaki; Ikabata, Yasuhiro; Wang, Qi; Nemoto, Daisuke; Sakamoto, Atsushi; Tanaka, Naoki; Seino, Junji; Nakai, Hiromi; Fukushima, Takanori

doi:10.1021/jacs.6b11984

Cited by 298 publications

(175 citation statements)

References 54 publications

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“…Recently, Huang and co‐workers described the use of terephthalic acid in combination with ammonia, potassium, or sodium, which leads to ionic terephthalate crystals with ultralong phosphorescence of up to 600 ms . Fukushima and co‐workers discovered in 2017, that facile phenylboronic esters ( 40 )–( 42 ) revealed blue fluorescence under excitation with 254 nm UV light, which changed to green long‐lived phosphorescence after switching off the lamp (Figure ) . This phenomenon was just detected in the crystalline state and not when ground samples were used.…”

Section: Crystallisation‐induced Phosphorescencementioning

confidence: 99%

Phosphorescence Through Hindered Motion of Pure Organic Emitters

Hayduk

Riebe

Voskuhl

2018

Chemistry A European J

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This minireview deals with the phenomenon of room-temperature phosphorescence induced by aggregation or crystallisation. Recent achievements, as well as novel classes of these unique luminophores, are put in to focus. In this fashion, different compounds, which reveal delayed fluorescence or phosphorescence upon fixation in a crystal lattice or within aggregates are described. Furthermore, the photophysical properties, the origin of the long-lived triplet states, and the possible applications of these fascinating classes of molecules are also discussed. To conclude, a short overview about the state of art in the field of pure organic phosphors at room temperature is presented.

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Section: Crystallisation‐induced Phosphorescencementioning

confidence: 99%

Phosphorescence Through Hindered Motion of Pure Organic Emitters

Hayduk

Riebe

Voskuhl

2018

Chemistry A European J

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“…In the literature, two main approaches have been developed to overcome those issues and achieve persistent RTP in aerated atmosphere. [16] Earlier this year, Su et al designed an organic molecule that is able to participate in multiple hydrogen bondings. [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.…”

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confidence: 99%

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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“…Another desirable feature of the emitting molecules is that they possess simple and small structures that allow broadening the scope of their applications. Therefore, single‐benzene molecules have recently attracted considerable attention as rigid and simple frameworks for its use in emitting organic material . For the development of emitters that retain the advantages of the hexagonal structure, a single‐benzene molecule should be designed, which should be characterised by ( i ) a symmetric structure, ( ii ) low molecular weight (MW) and ( iii ) a small number of different constituting atoms.…”

Section: Methodsmentioning

confidence: 99%

“…Shimizu and Hiyama's group reported low MW molecules based on a single‐benzene framework with π‐expanding vinylene moiety, 1,4‐bis(alkenyl)‐2,5‐dipiperidinobenzenes [symmetry, MW>296, HCN+O or F], for highly efficient solid emitters (Scheme a) . On the other hand, the expansion of the π‐system was shown not to be essential for the low‐energy emission, which was achieved with molecules based on functionalized benzene without conjugated substituents (Scheme b–e) . Kim's group designed efficient room temperature phosphorescent crystals based on benzene having alkoxy, aldehyde and bromine groups [unsymmetric, MW=385, HCOBr] .…”

Section: Methodsmentioning

confidence: 99%

2,5‐Dimethoxybenzene‐1,4‐dicarboxaldehyde: An Emissive Organic Crystal and Highly Efficient Fluorescent Waveguide

2019

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To identify the simplest organic structure for an emitter, we focused on 2,5‐dimethoxybenzene‐1,4‐dicarboaldehyde. This symmetric molecule has a very low molecular weight (MW=194), a single benzene unit, and consists of only three elements (H, C and O). It forms highly efficient and pure emitting crystals (λem=499 nm, ΦF=0.42, FWHM=42 nm) due to the rigid structure based on the single benzene framework and four intramolecular hydrogen bonds between electron‐donating methoxy and electron‐accepting aldehyde groups. This crystal acts as a good optical waveguide with pure green emission (FWHM=34 nm) and very low loss coefficient (0.00120 dB/μm).

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Unveiling a New Aspect of Simple Arylboronic Esters: Long-Lived Room-Temperature Phosphorescence from Heavy-Atom-Free Molecules

Cited by 298 publications

References 54 publications

Phosphorescence Through Hindered Motion of Pure Organic Emitters

Phosphorescence Through Hindered Motion of Pure Organic Emitters

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

2,5‐Dimethoxybenzene‐1,4‐dicarboxaldehyde: An Emissive Organic Crystal and Highly Efficient Fluorescent Waveguide

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