Green electrogenerated chemiluminescence using a quinacridone derivative as a guest molecule

Koinuma, Yugo; Ishimatsu, Ryoichi; Kato, Emiri; Mizuno, Jun; Kasahara, Takashi

doi:10.1016/j.elecom.2021.107047

Cited by 10 publications

(7 citation statements)

References 27 publications

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“…13 Although traditional ECL systems contain a single emitting species, more recently, ECL solutions containing multiple luminescent materials have been proposed. [14][15][16][17][18][19][20] In 2013, Nobeshima demonstrated an ACdriven white emission cell using yellow and blue fluorescent materials (rubrene and 9,10-diphenylanthracene). 14 Since 2014, we have been investigating host-guest ECL systems by referring to the literature on organic light-emitting diodes (OLEDs).…”

Section: Introductionmentioning

confidence: 99%

“…14 Since 2014, we have been investigating host-guest ECL systems by referring to the literature on organic light-emitting diodes (OLEDs). [15][16][17][18][19][20] Generally, OLEDs have a thin emitting layer containing host and guest materials, and carrier injection and transport layers are used to balance the number of electrons and holes in the emitting layer. Electroluminescence is obtained by energy transfer from the excited host molecules to the guests.…”

Section: Introductionmentioning

confidence: 99%

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Bright Yellow Electrogenerated Chemiluminescence Cell Using a Rubrene Solution Doped with an Emitting Assist Dopant

et al. 2023

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We demonstrated that the electrogenerated chemiluminescence (ECL) performances of 5,6,11,12-tetraphenyltetracene (rubrene)-based devices can be significantly enhanced by using an emitting assist dopant. We prepared an ECL solution by dissolving rubrene and 4-(di-p-tolylamino)-4′-[(di-p-tolylamino)styryl]stilbene (DPAVB) in an organic solvent. A microfluidic ECL cell having the prepared solution exhibited a bright yellow ECL emission from rubrene with a maximum luminance of 292 cd m −2 at 6.0 V and a maximum current efficiency of 4.50 cd A −1 at 5.5 V. Moreover, a current efficiency of over 3.0 cd A −1 was maintained from 3.0 to 6.5 V. Furthermore, the device lifetime was improved in comparison with the rubrene solution without DPAVB. The emission mechanism was discussed using cyclic voltammogram data. The DPAVB molecule was found to be more readily oxidized and more difficult to be reduced than rubrene. The excited rubrene molecules were expected to be produced efficiently in the device by the electron transfer reactions between rubrene •− and DPAVB •+ as well as rubrene •− and rubrene •+ . Based on the findings, we concluded that the enhanced device characteristics were primarily attributed to the well-balanced generation of radical cations and anions.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Bright Yellow Electrogenerated Chemiluminescence Cell Using a Rubrene Solution Doped with an Emitting Assist Dopant

et al. 2023

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“…In addition, the use of expensive metals, even at low concentrations can hinder a potential large‐scale industrialization of such derivatives. On the other hand, organic molecules allow limitless possibilities in order to control the electronic properties and the resulting ECL capability [22–26] . One promising organic moiety, which can be prepared in only two steps on a multi‐ton‐scale is the highly fluorescent but overlooked benzothioxanthene (BTX) structure.…”

Section: Introductionmentioning

confidence: 99%

“…On the other hand, organic molecules allow limitless possibilities in order to control the electronic properties and the resulting ECL capability. [22][23][24][25][26] One promising organic moiety, which can be prepared in only two steps on a multi-ton-scale is the highly fluorescent but overlooked benzothioxanthene (BTX) structure. BTX has never been investigated in the context of ECL, despite its great potential, and is thus evaluated herein.…”

Section: Introductionmentioning

confidence: 99%

Benzothioxanthene Dicarboximide as a Tuneable Electrogenerated Chemiluminescence Dye

Dauphin

Castán

et al. 2022

ChemElectroChem

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Overlooked for years, the promising benzothioxanthene dicarboximide (BTXI) structure is nonetheless known to be an excellent fluorophore. As a further step towards the exploration of this rylene structure, the generation of electrochemiluminescence (ECL) in acetonitrile solutions is investigated herein as well as its direct comparison with a diphenylamine (DPA) derivative. Electrochemical characterization shows that the bare BTXI can be reversibly reduced or oxidized, characteristics which suggest the possibility that the electrogenerated reactive species can be exploited in the context of ECL. As a result, the BTXI moiety was found to be ECL-active in both annihilation and co-reactant mechanisms. Tri-n-propylamine (TPA) and benzoyl peroxide (BPO) were selected as sacrificial co-reactants for promoting ECL. An ECL efficiency of 13 % (BTXI) and 6 % (BTXI-DPA) compared to that of Ru(bpy) 3 2 + was found when using TPA in oxidative ECL. Moreover, the ECL efficiency increased to 75 % and 55 % of Ru(bpy) 3 2 + with BPO (i. e. reductive-oxidation ECL) for BTXI and BTXI-DPA, respectively. These results can be understood by calculating the free enthalpy of the redox reactions associated with each ECL pathway. Although the BTXI-DPA red emitter exhibits more suitable thermodynamic properties, the BTXI green emitter is nonetheless more effective in combination with a co-reactant due to a much larger photoluminescence quantum yield. The ECL spectra of the two molecules are compared to their photoluminescence spectra, revealing the involvement of the same excited states in the two different photoemission processes. In turn, the chemical engineering of BTXI is shown to be an effective platform for achieving tuneable ECL generation.

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“…In our previous work, we proposed host-guest ECL solutions by referring to the emission mechanism of organic light-emitting diodes (OLEDs). [17][18][19][20] In general, OLED devices are composed of organic semiconductor thin films, and the emitting layer consists of a wide-energy-gap host material and a small amount of a guest material in order to obtain bright and efficient electroluminescence. [21][22][23][24][25][26][27][28] In 2014, we developed a red ECL solution using 5,6,11,12-tetraphenyltetracene (rubrene), which emits yellow fluorescence, as a host material.…”

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confidence: 99%

Sky-blue electrogenerated chemiluminescence using anthracene derivatives as host and guest molecules

Kato

Ishimatsu

Koinuma

et al. 2022

Jpn. J. Appl. Phys.

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We developed a solution-based sky-blue electrogenerated chemiluminescence (ECL) cell using two kinds of anthracene derivatives. 9,9’-10,10’-Tetraphenyl-2-2’-bianthracene (TPBA) was used as a guest molecule, while 2-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), which emits deep-blue fluorescence, was used as a host molecule. The microfluidic ECL cell with the TPBA-doped TBADN solution exhibited bright emission from TPBA with a maximum luminance of 7.7 cd m-2. By contrast, the ECL intensity was found to be considerably weak when the host was absent in the solution. We believe that the proposed host-guest solution will contribute to the future development of highly efficient ECL display devices.

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Green electrogenerated chemiluminescence using a quinacridone derivative as a guest molecule

Cited by 10 publications

References 27 publications

Bright Yellow Electrogenerated Chemiluminescence Cell Using a Rubrene Solution Doped with an Emitting Assist Dopant

Bright Yellow Electrogenerated Chemiluminescence Cell Using a Rubrene Solution Doped with an Emitting Assist Dopant

Benzothioxanthene Dicarboximide as a Tuneable Electrogenerated Chemiluminescence Dye

Sky-blue electrogenerated chemiluminescence using anthracene derivatives as host and guest molecules

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