An Acid‐Responsive Single Trichromatic Luminescent Dye That Provides Pure White‐Light Emission

Imamura, Keigo; Ueno, Yoshifumi; Akimoto, Seiji; Eda, Kazuo; Du, Yiqun; Eerdun, Chaolu; Wang, Meiling; Nishinaka, Kumiko; Tsuda, Akihiko

doi:10.1002/cptc.201700108

Cited by 8 publications

(4 citation statements)

References 33 publications

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“…We previously reported the synthesis of a π-conjugated phenylene-bridged bipyrrole bearing N-alkylimino groups (BPI-1), and found that it is an acid-responsive single trichromatic luminescent dye capable of emitting pure white light (WL) (Imamura et al, 2017). The blue-light-emitting BPI-1 exhibits dramatic color changes in fluorescence to orange and green upon mono-and diprotonation, respectively, providing a wide emission band in the range of λ = 400-800 nm that provide WL when the compound is in a dynamic equilibrium between the three states.…”

Section: Introductionmentioning

confidence: 99%

A Chiral Metal-Organic 1D-Coordination Polymer Upon Complexation of Phenylene-Bridged Bipyrrole and Palladium (II) Ion

Nishinaka

Han

et al. 2020

Front. Chem.

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Metal-organic 1D-coordination polymers, having unique electronic and optical properties, are expected to be a novel advanced functional material capable of fabricating smart plastics, films, and fibers. In this study, we have synthesized a novel metal-organic 1D-coordination polymer composed of a phenylene-bridged bipyrrole bearing N-alkylimino groups (BPI) and palladium(II) ion. The BPI and Pd(II) form square planar bis(bidentate) complex to form a metal coordinated π-conjugation polymer (Poly-BPI/Pd). It is stable in solutions at room temperature, and allowed measurement of its average molecular weight in SEC (Mw = 106,000 and Mn = 18,000, Mw/Mn = 5.88). It also provided a reversible multi redox profile in cyclic voltammetry, most likely originating from strong π-electronic interactions between the BPI components via Pd ion. A variety of substituent groups can be attached to the imino-nitrogens of BPI. A coordination polymer composed of a BPI derivative bearing chiral alkyl chains and Pd(II) showed strong circular dichroism (CD) in the solution due to the unidirectional chiral conformation of the BPI components in the polymer backbone.

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Section: Introductionmentioning

confidence: 99%

A Chiral Metal-Organic 1D-Coordination Polymer Upon Complexation of Phenylene-Bridged Bipyrrole and Palladium (II) Ion

Nishinaka

Han

et al. 2020

Front. Chem.

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“…Luminescent materials exhibiting multicolor emission have attracted considerable attention due to their potential applications in many areas. Mixing emission colors in the visible region may generate white light − that could be used in energy-efficient organic light-emitting diodes (OLEDs). − Two or more emission bands from a single fluorophore could be exploited in the self-calibrating ratiometric sensing technologies, − which offer the advantage of minimizing systematic errors originating from concentration variation, excitation power fluctuation, and photobleaching of the fluorophore . Properties of the microenvironment surrounding a multiple-emission fluorophore can be extracted through monitoring the changes of various emission bands that have uneven responses to environmental factors such as polarity , or viscosity. , …”

Section: Introductionmentioning

confidence: 99%

Excitation-Dependent Multiple Fluorescence of a Substituted 2-(2′-Hydroxyphenyl)benzoxazole

et al. 2018

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Excitation-dependent multiple fluorescence of a 2-(2′hydroxyphenyl)benzoxazole (HBO) derivative ( 1) is described. Compound 1 contains the structure of a charge-transfer (CT) 4hydroxyphenylvinylenebipy fluorophore and an excited-state intramolecular proton transfer capable (ESIPT-capable) HBO component that intersect at the hydroxyphenyl moiety. Therefore, both CT and ESIPT pathways, while spatially mostly separated, are available to the excited state of 1. The ESIPT process offers two emissive isomeric structures (enol and keto) of 1 in the excited state, while the susceptibility of 1 to a base adds another option to tune the composite emission color. In addition to the ground-state acid−base equilibrium that can be harnessed for the control of emission color by excitation energy, compound 1 exhibits excitation-dependent emission that is attributed to solventaffected ground-state structural changes. Therefore, depending on the medium and excitation wavelength, the emission from the enol, keto, and anion forms could occur simultaneously, which are in the color ranges of blue, green, and orange/red, respectively. A composite color of white with CIE coordinates of (0.33, 0.33) can be materialized through judicious choices of medium and excitation wavelength.

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“…Indole with its larger aromatic structure also allowed formylation at the 3-position in 86% yield, but benzofuran provided the 2-formyl product in relatively low yield ( 1g and 1h , respectively). Since VR 2 efficiently reacted with 1 H -pyrrole, we next carried out one-pot formylation reactions of bispyrroles, which are utilized for fabricating functional supramolecular architectures and macrocyclic rings . Bispyrrole derivatives, including an aliphatic and an aromatic bridge, both provided the corresponding bisformyl products in high yields ( 1i and 1j ).…”

Section: Resultsmentioning

confidence: 99%

Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses

et al. 2021

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The Vilsmeier reagent (VR), first reported a century ago, is a versatile reagent in a variety of organic reactions. It is used extensively in formylation reactions. However, the synthesis of VR generally requires highly toxic and corrosive reagents such as POCl 3 , SOCl 2 , or COCl 2 . In this study, we found that VR is readily obtained from a CHCl 3 solution containing N,Ndimethylformamide or N,N-dimethylacetamide upon photoirradiation under O 2 bubbling. The corresponding Vilsmeier reagents were obtained in high yields with the generation of gaseous HCl and CO 2 as byproducts to allow their isolations as crystalline solid products amenable to analysis by X-ray crystallography. With the advantage of using CHCl 3 , which bifunctionally serves as a reactant and a solvent, this photo-on-demand VR synthesis is available for one-pot syntheses of aldehydes, acid chlorides, formates, ketones, esters, and amides.

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An Acid‐Responsive Single Trichromatic Luminescent Dye That Provides Pure White‐Light Emission

Cited by 8 publications

References 33 publications

A Chiral Metal-Organic 1D-Coordination Polymer Upon Complexation of Phenylene-Bridged Bipyrrole and Palladium (II) Ion

A Chiral Metal-Organic 1D-Coordination Polymer Upon Complexation of Phenylene-Bridged Bipyrrole and Palladium (II) Ion

Excitation-Dependent Multiple Fluorescence of a Substituted 2-(2′-Hydroxyphenyl)benzoxazole

Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses

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