Fabrication of Colorless Organic Materials Exhibiting White Luminescence Using Normal and Excited-State Intramolecular Proton Transfer Processes

Shono, Hideaki; Ohkawa, Tatsuya; Tomoda, Haruhiko; Mutai, Toshiki; Araki, Koji

doi:10.1021/am200022z

Cited by 129 publications

(66 citation statements)

References 15 publications

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“…[ 48 ] Araki and his coworkers obtained white-light emission from the solid-state mixtures of two 2-phenylimidazo[1,2-a]pyridine (PIP) -based molecules exhibiting normal and ESIPT luminescence as blue-and yellow-emission, respectively, by various fabrication methods. [ 114 ] For example, they prepared mixed powders of H2 ( λ max = 536 nm, Φ PL = 0.31) and M2 ( λ max = 422 nm, Φ PL = 0.15) by grinding in a mortar. ( Figure 24 a) A mixed solid with a ratio of H2:M2 = 3:10 by weight showed a bright white luminescence ( Φ PL = 0.24) at the CIE coordinate of (x, y) = (0.30, 0.31).…”

Section: Effi Cient White-light Generation From Mixturesmentioning

confidence: 99%

Advanced Organic Optoelectronic Materials: Harnessing Excited‐State Intramolecular Proton Transfer (ESIPT) Process

2011

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Recently, organic fluorescent molecules harnessing the excited-state intramolecular proton transfer (ESIPT) process are drawing great attention due to their unique photophysical properties which facilitate novel optoelectronic applications. After a brief introduction to the ESIPT process and related photo-physical properties, molecular design strategies towards tailored emission are discussed in relation to their theoretical aspects. Subsequently, recent studies on advanced ESIPT molecules and their optoelectronic applications are surveyed, particularly focusing on chemical sensors, fluorescence imaging, proton transfer lasers, and organic light-emitting diodes (OLEDs).

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Section: Effi Cient White-light Generation From Mixturesmentioning

confidence: 99%

Advanced Organic Optoelectronic Materials: Harnessing Excited‐State Intramolecular Proton Transfer (ESIPT) Process

2011

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“…[1][2][3][4][5] In particular, some of their derivatives have been used as current clinical treatments and they have good pharmaceutical activity against a range of disease targets. [1][2][3][4][5] In particular, some of their derivatives have been used as current clinical treatments and they have good pharmaceutical activity against a range of disease targets.…”

Section: Introductionmentioning

confidence: 99%

Mechanism of the gold(i)-catalyzed synthesis of imidazo-pyrimidines and imidazo-pyrazines via [3 + 2] dipolar cycloaddition: a DFT study

Zhang

Geng

2016

RSC Adv.

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Density functional theory calculations have been carried out to study the mechanisms of gold(I)-catalyzed [3 + 2] cycloaddition reactions of pyridinium N-(heteroaryl)-aminides, as nucleophilic nitrenoids, with electron-rich alkynes, leading to imidazo-pyrimidines and imidazo-pyrazines. The calculation results suggest that the reaction mainly involves two plausible pathways leading to different products, since two carbon atoms of the asymmetric alkyne are attacked selectively by the aminide nitrogen atom. These reaction steps include C-C bond activation of the alkyne by the gold complex, a bimolecular nucleophilic attack, a closed-loop process and migration of the pyridine molecule to finally give cycloaddition products. The closed-loop process is the rate-limiting step for the whole catalytic reaction and the energy barrier shows that the pathway of the nucleophile onto the amide carbon atom of the alkyne with the electron-withdrawing group is favored. Through a detailed mechanistic investigation, we have explained the regioselectivity and the major/minor products observed by Davies et al. in gold(I)catalyzed [3 + 2] cycloaddition reactions of nucleophilic nitrenoids with electron-rich alkynes. Fig. 3 Free energy profiles calculated for the gold-catalyzed [2 + 3] cycloaddition of pyridinium N-(2-pyrimidinyl) aminide with thiophen-2ynamide. The relative free energies are given in kcal mol À1 . This journal is View Article Online found for b-TS2 in comparison to that for a-TS2 may be owing to the effect of the thienyl group. The next step for pyridine migration results in the new Au imidazole intermediate, b-IN3.Then, b-IN3, through a barrier-free process, easily generates the nal product (P3), regenerating the catalyst (CA). The whole catalytic cycle is exothermic by À65.2 kcal mol À1 . Fig. 4 Fully optimized structures of the intermediates and the transition states for pathway b are shown in Fig. 3, with selected bond lengths inÅ. The H atoms in structures are omitted for clarity. 62104 | RSC Adv., 2016, 6, 62099-62108 This journal is

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“…Moreover, the aqueous medium cannot quench the ESIPT emission of compound 1 , because the intramolecular hydrogen bond NH···N is protected by its unique structure . This condition significantly differs from conventional ESIPT chromophores, where ESIPT emission is typically disrupted due to the formation of intermolecular hydrogen bonds …”

Section: Introductionmentioning

confidence: 98%

Accurate description of excited state intramolecular proton transfer that involves zwitterionic state using optimally tuned range‐separated time‐dependent density functional theory

Zhou

2018

Int J of Quantum Chemistry

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Excited‐state intramolecular proton transfer (ESIPT) reaction typically involves the excited‐state of charge‐transfer (CT) character. Thus, locating the transition state (TS) and providing an accurate description for the canonical and tautomeric forms play important roles and remain as challenges in the investigation of ESIPT reaction. In this study, the ESIPT reaction of a recently developed ESIPT chromophore (compound 1) (N. Suzuki et al., Angew. Chem. Int. Ed. 2014, 53, 8231) that involves the CT and zwitterionic states has been investigated using the time‐dependent density functional theory (TDDFT) method with different functionals and the second‐order algebraic diagrammatic construction (ADC(2)) method. Theoretical results suggest that the TDDFT method with IP‐tuned range‐separated functional should be applied to investigate ESIPT reaction when the zwitterionic or CT states are involved. In addition, the TS geometries for the ESIPT reaction of compound 1 in three different solvents have been successfully located, and the Gibbs free energies along the reaction path have been provided. The calculated results can clearly explain the experimentally observed solvent‐dependent fluorescence of compound 1.

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Fabrication of Colorless Organic Materials Exhibiting White Luminescence Using Normal and Excited-State Intramolecular Proton Transfer Processes

Cited by 129 publications

References 15 publications

Advanced Organic Optoelectronic Materials: Harnessing Excited‐State Intramolecular Proton Transfer (ESIPT) Process

Advanced Organic Optoelectronic Materials: Harnessing Excited‐State Intramolecular Proton Transfer (ESIPT) Process

Mechanism of the gold(i)-catalyzed synthesis of imidazo-pyrimidines and imidazo-pyrazines via [3 + 2] dipolar cycloaddition: a DFT study

Accurate description of excited state intramolecular proton transfer that involves zwitterionic state using optimally tuned range‐separated time‐dependent density functional theory

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