2-Pyridone-based fluorophores containing 4-dialkylamino-phenyl group: Synthesis and fluorescence properties in solutions and in solid state

Hagimori, Masayori; Shigemitsu, Yasuhiro; Murakami, Ryo; Yokota, Kenichirou; Nishimura, Yasuhisa; Mizuyama, Naoko; Wang, Bo-Cheng; Tai, Chen-Kuen; Wang, San-Lang; Shih, Tzenge‐Lien; Wu, Kuen-Da; Huang, Zhi-Shuan; Tseng, Shih-Chuw; Lü, Jie; Wei, Ho‐Hsiang; Nagaoka, Junko; Mukai, Takahiro; Kawashima, Shinichi; Kawashima, Keisuke; Tominaga, Yoshinori

doi:10.1016/j.dyepig.2015.09.017

Cited by 13 publications

(13 citation statements)

References 24 publications

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“…2‐pyridones are intensely luminescent chromophoric units [136,137] and their LC properties are also known [138,139] . Motivated by these, Adhikari et al.…”

Section: Dlc Based Materials As Emitters In Oledsmentioning

confidence: 99%

Discs to a ‘Bright’ Future: Exploring Discotic Liquid Crystals in Organic Light Emitting Diodes in the Era of New‐Age Smart Materials

Sharma

Sengupta

et al. 2022

The Chemical Record

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With the advent of a new decade and the paradigm shift of every sphere of urban life to virtual platforms, it has become imperative for the global researcher community to channelize efforts into upgradation of the existing display‐technology. In this context, discotic liquid crystals (DLCs) are a class of self‐assembling organic materials that are recently being explored in fabricating the emissive layers of organic light emitting diodes (OLEDs). With their unique inherent structural and functional properties, they have the potential to challenge the currently prevailing OLED‐emitters. Yet the applications of this promising class of materials in OLEDs have not been comprehensively reviewed in literature till now. In this account, we present an overview of the developments in the field of luminescent DLC‐based emitters, supported by their associated photophysical phenomena and their performance parameters as emitters in fabricated OLED devices.

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“…2‐pyridones are intensely luminescent chromophoric units [136,137] and their LC properties are also known [138,139] . Motivated by these, Adhikari et al.…”

Section: Dlc Based Materials As Emitters In Oledsmentioning

confidence: 99%

Discs to a ‘Bright’ Future: Exploring Discotic Liquid Crystals in Organic Light Emitting Diodes in the Era of New‐Age Smart Materials

Sharma

Sengupta

et al. 2022

The Chemical Record

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“…Fluorescent compounds have attracted considerable attention as functional materials because of their applications in areas such as information devices, displays, and clinical diagnosis [ 1 – 3 ]. Organic compounds with planar structures and large π systems exhibit strong fluorescence in dilute solutions [ 4 – 5 ]. However, these compounds usually form aggregate structures in high-concentration solutions, and their emission efficiency, chromogenic properties, and light sensitivity decrease rapidly [ 5 – 6 ].…”

Section: Introductionmentioning

confidence: 99%

“…Organic compounds with planar structures and large π systems exhibit strong fluorescence in dilute solutions [ 4 – 5 ]. However, these compounds usually form aggregate structures in high-concentration solutions, and their emission efficiency, chromogenic properties, and light sensitivity decrease rapidly [ 5 – 6 ]. In recent years, contrary to conventional fluorescent compounds, aggregation-induced emission enhancement (AIEE)-based compounds that exhibit strong fluorescence in aggregate structures have been reported [ 7 – 10 ].…”

Section: Introductionmentioning

confidence: 99%

“…Previously, we have reported various pyridine derivatives, including polysubstituted pyridines and fused pyridines, which exhibited strong fluorescence in organic solvents (ethanol and dichloromethane) [ 16 – 19 ], while their fluorescence in aqueous media was quenched due to aggregation-caused quenching (ACQ) [ 10 ]. Generally, the restriction of intermolecular π–π interactions in highly planar compounds plays a key role in aggregate structures exhibiting fluorescence [ 5 – 6 10 ]. In addition, intramolecular mechanisms, such as intramolecular rotation (RIR), intramolecular charge transfer, and twisted intramolecular charge transfer (TICT) are involved in AIEE [ 20 – 22 ].…”

Section: Introductionmentioning

confidence: 99%

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Syntheses of novel pyridine-based low-molecular-weight luminogens possessing aggregation-induced emission enhancement (AIEE) properties

Hagimori

Yoshida

Nishimura

et al. 2022

Beilstein J. Org. Chem.

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Novel pyridine-based fluorescing compounds, viz. pyrido[1,2-a]pyrrolo[3,4-d]pyrimidines 3a,b and N-methyl-4-((pyridin-2-yl)amino)maleimides 4a–e, were selectively prepared by a one-pot reaction between a functionalized maleimide and 2-aminopyridines with electron-donating or electron-withdrawing groups at position 5 and were investigated photophysically and computationally. The photophysical studies revealed that all the synthesized compounds exhibited fluorescence in organic solvents, while N-methyl-4-((pyridin-2-yl)amino)-substituted maleimide derivatives 4a–e, which are based on an acceptor–donor–acceptor (A–D–A) system, exhibited aggregation-induced emission enhancement (AIEE) properties in aqueous media. Compounds 4a and 4e, bearing electron-withdrawing groups (Br and CF3, respectively) showed 7.0 and 15 times fluorescence enhancement. Time-dependent density functional theory (TD-DFT) calculations were performed to gain better insight into the electronic nature of the compounds with and without AIEE properties.

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“…Moreover, 2-pyridone ring is one of the most classes of fluophores, with several photo functional applications [18], this skeleton exhibit a strong emission in different regions of spectrum. Recently, they are a much interest in the development of convenient methodologies of the synthesis of 2-pyridones from simple and available starting materials to their fluorescent properties [19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Novel bis-(3-cyano-2-pyridones) derivatives: synthesis and fluorescent properties

et al. 2021

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Novel substituted bis-(3-cyano-2-pyridone) derivatives were prepared via a powerful method using enaminonitriles push-pull dienes as key building blocks. The synthesis was performed in three-steps from easily accessible starting materials in good yields. All target products were structurally elucidated by spectroscopic data. The reaction mechanism for formation of bis (3cyano-2-pyridone) derivatives was proposed. The structures of enaminonitriles 3a and bispyridones 4c were confirmed by single-crystal X-ray diffraction. The florescent study of some bis (3-cyano-2-pyridones) derivatives was reported.

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2-Pyridone-based fluorophores containing 4-dialkylamino-phenyl group: Synthesis and fluorescence properties in solutions and in solid state

Cited by 13 publications

References 24 publications

Discs to a ‘Bright’ Future: Exploring Discotic Liquid Crystals in Organic Light Emitting Diodes in the Era of New‐Age Smart Materials

Discs to a ‘Bright’ Future: Exploring Discotic Liquid Crystals in Organic Light Emitting Diodes in the Era of New‐Age Smart Materials

Syntheses of novel pyridine-based low-molecular-weight luminogens possessing aggregation-induced emission enhancement (AIEE) properties

Novel bis-(3-cyano-2-pyridones) derivatives: synthesis and fluorescent properties

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