Acid‐Responsive Absorption and Emission of 5‐<i>N</i>‐Arylaminothiazoles: Emission of White Light from a Single Fluorescent Dye and a Lewis Acid

Yamaguchi, Kirara; Murai, Toshiaki; Guo, Jing‐Dong; Sasamori, Takahiro; Tokitoh, Norihiro

doi:10.1002/open.201600059

Cited by 34 publications

(16 citation statements)

References 51 publications

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“…Variation in the color of a dye or pigment due to changes in its immediate environment is referred to as chromism. It is a key feature that has led to sensing applications, perhaps most importantly involving acid–base equilibria (e.g. halochromism of pH indicators).…”

Section: Introductionmentioning

confidence: 99%

Structural Modulation of Chromic Response: Effects of Binding‐Site Blocking in a Conjugated Calix[4]pyrrole Chromophore

et al. 2018

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Herein, we modulate the chromic response of a highly colored tetrapyrrole macrocycle, namely, tetrakis(3,5‐di‐tert‐butyl‐4‐oxocyclohexadien‐2,5‐yl)porphyrinogen (OxP) by structural modification. N‐Benzylation at the macrocyclic nitrogen atoms leads to stepwise elimination of the two calix[4]pyrrole‐type binding sites of OxP and serial variation of the chromic properties of the products, double N‐benzylated Bz2OxP and tetra N‐benzylated Bz4OxP. The halochromic (response to acidity) and solvatochromic (response to solvent polarity) properties were studied by using UV/Vis spectroscopy and NMR spectroscopy in nonpolar organic solvents. Titration experiments were used to generate binding isotherms to elucidate their binding properties with difluoroacetic acid. Differences in the halochromic properties of the compounds allowed construction of a colorimetric scale of acidity in nonpolar solvents, as the compounds in the series OxP, Bz2OxP, and Bz4OxP are increasingly difficult to protonate but maintain their propensity to change color upon protonation. The concurrent effects of binding‐site blocking and modulation of acidity sensitivity are important new aspects for the development of colorimetric indicators.

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Section: Introductionmentioning

confidence: 99%

Structural Modulation of Chromic Response: Effects of Binding‐Site Blocking in a Conjugated Calix[4]pyrrole Chromophore

et al. 2018

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“…4,123.3,124.0,126.9,127.4,128.1,128.2,129.2,133.0,136.4,140.9,146.3,147.1,161.3;MS (EI) 3, 44.5, 120.5, 122.1, 123.1, 124.7, 126.0, 126.4, 127.6, 128.1, 129.0, 129.7, 13.04, 130.6, 132.5, 136.5, 137.8, 140.8, 144.3 44.5,121.6,123.5,126.8,127.4,128.0,128.3,129.3,129.5,132.9,138.7,141.0,142.0,146.3,149.2,160.2;MS (EI) 13 C NMR (CDCl3)  20. 7,21.3,44.5,120.4,121.0,121.5,121.6,125.8,126.2,126.7,126.9,127.0,127.3,127.9,128.8,129.0,129.4,129.7,129.9,130.2,132.9,144.3,165.2;MS (EI)…”

Section: N-benzyl-4-(methylsulfanyl)benzothioamide (1a)mentioning

confidence: 99%

“…4 In particular, we recently established synthetic methods for compounds with N-arylamino groups at the 5-position of thiazoles 5 in a series on main group chemistry. 6 We also determined their fundamental photophysical properties 5b and used them in white-light emission, 7 the generation of radical cations showing near-infrared absorption, 8 and the detection of halogenated solvents via vapochromic behaviors. 9 In some cases, pyridyl groups were used as anchor moieties to interact with Lewis acidic compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Photophysical Properties of 5-N-Arylaminothiazoles with Sulfur-Containing Groups on the Aromatic Ring at the 2-Position

Murai¹,

Furukawa²,

Yamaguchi³

2018

HETEROCYCLES

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5-Amino-2-(4-methylsulfanylphenyl)thiazoles were prepared by reacting 4-methylsulfanylbenzthioamides and N,N-diarylthioformamides. Demethylaiton of the resulting thiazoles gave 4-sulfhydrylphenylthiazoles. Starting from these thiazoles, a range of thiazoles with sulfur-containing functional groups were prepared. Oxidation of the thiazoles also gave thiazoles with sulfenyl and sulfonyl groups. The photophysical properties of a series of thiazoles were determined. The effects of sulfur-containing functional groups on the electronic structures of the thiazoles were elucidated by DFT calculations. Oxidation of the divalent sulfur atoms introduced to thiazoles helped to lower the energy levels of the LUMOs of the resulting thiazoles.

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“…The two forms should emit complementary colors and can consist of monomer/excimer, 19,20,21 neutral/(de)protonated species, 14,22,23,24 or free/complexed ligand. 24,25 We recently described methoxy-substituted arylvinylpyrimidine derivatives that emit blue light in their neutral form and red light upon protonation. 26,27 A mixture of the two forms 10.1002/chem.202000817…”

Section: Introductionmentioning

confidence: 99%

Push–Pull (Iso)quinoline Chromophores: Synthesis, Photophysical Properties, and Use for White‐Light Emission

Allaoui

Gall

Fihey

et al. 2020

Chemistry A European J

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The photophysical properties of a series of conjugated push-pull (iso)quinolines have been studied. The compounds were synthesized by well-established and straightforward methodologies. The materials exhibited not only emission solvatochromism in a variety of non-polar solvents, but also tunable halochromism. Some of the compounds remained moderately luminescent after protonation and these had a red emissive form, which was used to obtain white light emission, both in solution and in thin film, by the controlled protonation of the initially blue-green emitting materials. This methodology has potential applications in white OLED fabrication with two forms of a single emitter in equilibrium.

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Acid‐Responsive Absorption and Emission of 5‐N‐Arylaminothiazoles: Emission of White Light from a Single Fluorescent Dye and a Lewis Acid

Cited by 34 publications

References 51 publications

Structural Modulation of Chromic Response: Effects of Binding‐Site Blocking in a Conjugated Calix[4]pyrrole Chromophore

Structural Modulation of Chromic Response: Effects of Binding‐Site Blocking in a Conjugated Calix[4]pyrrole Chromophore

Synthesis and Photophysical Properties of 5-N-Arylaminothiazoles with Sulfur-Containing Groups on the Aromatic Ring at the 2-Position

Push–Pull (Iso)quinoline Chromophores: Synthesis, Photophysical Properties, and Use for White‐Light Emission

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