Synthesis and Fluorescence Properties of Thiazole–Boron Complexes Bearing a β-Ketoiminate Ligand

Kubota, Yasuhiro; Tanaka, Syunki; Funabiki, Kazumasa; Matsui, Masaki

doi:10.1021/ol302179r

Cited by 143 publications

(74 citation statements)

References 63 publications

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“…By expanding the conjugation systems with fused heterocycles involving the nitrogen atom in the ketoiminate complexes, various AIE-active molecules can be obtained. Kubota et al 50 presented AIE-active molecules and a complex with the same degree of fluorescence quantum yields in both the solution and solid states. Sun and colleagues reported the creation of quinoxaline-fused complexes.…”

Section: Versatility Of Boron Diketonates K Tanaka and Y Chujomentioning

confidence: 99%

Recent progress of optical functional nanomaterials based on organoboron complexes with β-diketonate, ketoiminate and diiminate

2015

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The synthesis and application of organoboron complexes are a highly relevant topic owng to their unique characteristics. Based on their emissive properties, these complexes have been used to make novel optical materials and devices; boron β-diketonate is a simple and robust organoboron complex. From a series of recent studies, unique and versatile optical properties have been reported. In this review, we introduce the results of primarily recent studies on boron diketonate and related compounds containing polymers and particularly explain their optical properties. Initially, the multi-emission of boron diketonate derivatives and its application to biotechnology are explained. Next, the formation of nanostructures and its emission properties are demonstrated. The modulation of optical properties by mechanical stress is also presented. Finally, recent progress in the development of solid-emissive materials are shown with boron diketonates and their derivatives, which have aggregation-induced emission properties. The versatility of boron diketonates as a building block for the preparation of functional optical materials is the focus of this review.

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Section: Versatility Of Boron Diketonates K Tanaka and Y Chujomentioning

confidence: 99%

Recent progress of optical functional nanomaterials based on organoboron complexes with β-diketonate, ketoiminate and diiminate

2015

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“…Furthermore, the p-p interaction reduced between adjacent layers and thus simultaneously increasing the uorescence intensity. 36 In addition, weak interactions e.g.…”

Section: Molecular Packingmentioning

confidence: 99%

Engineering fused coumarin dyes: a molecular level understanding of aggregation quenching and tuning electroluminescence via alkyl chain substitution

et al. 2014

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Simple molecular structures capable of emitting over the entire visible range are still a challenge. Planar molecular structures have the drawback of fluorescence quenching in the solid state thus limiting their application fields. Combining long range excimer/exciplex emissions with a compound emission have been used to get white light. In this work, a series of new coumarin derivatives having a planar structure have been synthesized and characterized. The effects of systematic variation in alkyl chain functionalization providing morphological variations that permit interesting solid state emitting properties have been discussed simultaneously with electrochemical behavior and OLED (organic light emitting diode) device applications. Carbon chains containing 0-16 carbon atoms have been studied in order to conclude the results that systematic changes in alkyl group substitution can be utilized as a tool to tune the emitting color of these planar coumarins. Alkyl chains were introduced by O-acylation and O-benzoylation reaction on the hydroxyl group of parent coumarin 5. Thus the present strategy is also helpful in establishing a template to control the unproductive interchromophore electronic couplings.Solid state fluorescence properties support the crystal studies. Theoretical studies are also in agreement with experimental data. Electroluminescence of Device 2 with a turn on voltage (V on ) around 5-6 V having s-CBP doped with 1% of 8 having alkyl substitution of 2-carbons is found to exhibit white emission with CIE co-ordinates of (0.29, 0.34) which is close to white emission while the alkyl substitution of 14-carbons (compound 17) in Device 7 (V on ¼ 7 V) exhibited green emission. Thus a strategy helpful to tune the electroluminescence has been discussed.

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“…The structural and photophysical properties of different families of boron complexes have been reported in the literature, among which neutral, coordinately saturated, N,N (excluding BODIPYs), [15,19] N,N,O,O tetradentate, [20] O,N,O tridentate, [21] and N,O bidentate ligands have been described. The N,O chelating ligands are by far the most studied p-conjugated ligands, including a wide range of structures with single or multiple boron centers, mainly as hydroxyquinolate, [22] pyrene, [23] perylenetetracarboxylic diimides (PDIs), [24] and Schiff bases, [25] but some more exotic structures such as iminoketone [26] and azaoxobenzazulene [27] have also been reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Luminescent Ethynyl‐Extended Regioisomers of Borate Complexes Based on 2‐(2′‐Hydroxyphenyl)benzoxazole

Massue

Frath

Retailleau

et al. 2013

Chemistry A European J

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A series of thirteen luminescent tetrahedral borate complexes based on the 2-(2'-hydroxyphenyl)benzoxazole (HBO) core is presented. Their synthesis includes the incorporation of an ethynyl fragment by Sonogashira cross-coupling reaction, with the goal of extending the conjugation and consequently redshifting their emission wavelength. Different regioisomers, substituted in the 3-, 4-, or 5-position of the phenolate side of the HBO core, were studied in order to compare their photophysical properties. The complexes were characterized by X-ray diffraction and NMR, UV/Vis, and emission spectroscopy in solution and in the solid state. In all cases, complexation to boron leads to a donor-acceptor character that impacts their photophysical properties. Complexes with a 3- or 5-substituted fragment display mild to pronounced internal charge transfer (ICT), a feature strengthened by the presence of p-dibutylaminophenylacetylene in the molecular structure, protonation of the nitrogen atom of which leads to a significant blueshift and an increase in quantum yield. On the contrary, when the ethynyl module is grafted on the 4-position, narrow, structured, symmetrical absorption/emission bands are observed. Moreover, the fact that protonation has little effect on the emission maximum wavelength reveals singlet excited-state decay. Solid-state emission properties reveal a redshift compared to solution, explained by tight packing of the π-conjugated systems and the high planarity of the dyes. Subsequent connection of these complexes to other photoactive subunits (BODIPY, Boranil) provides dyads in which efficient cascade energy transfer is observed.

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Synthesis and Fluorescence Properties of Thiazole–Boron Complexes Bearing a β-Ketoiminate Ligand

Cited by 143 publications

References 63 publications

Recent progress of optical functional nanomaterials based on organoboron complexes with β-diketonate, ketoiminate and diiminate

Recent progress of optical functional nanomaterials based on organoboron complexes with β-diketonate, ketoiminate and diiminate

Engineering fused coumarin dyes: a molecular level understanding of aggregation quenching and tuning electroluminescence via alkyl chain substitution

Synthesis of Luminescent Ethynyl‐Extended Regioisomers of Borate Complexes Based on 2‐(2′‐Hydroxyphenyl)benzoxazole

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