Intermolecular hydrogen bonding-assisted high contrast fluorescent switch in the solid state

Lin, Qifei; Xiao, Shuzhang; Li, Ruohan; Tan, Ronghua; Wang, Sa

doi:10.1016/j.dyepig.2014.11.001

Cited by 10 publications

(2 citation statements)

References 40 publications

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“…In the criteria related to fluorescent In short, it is difficult to synthesise photochromic fluorescent diarylethenes with ideal properties and it is often not possible to predict all of the aforementioned properties. In this respect, it is important to synthesise different photochromic compounds that may exhibit fluorescence (14)(15)(16)(17)(18)(19)(20)(21)(22)(23).…”

Section: Introductionmentioning

confidence: 99%

Investigation of Photochromic Fluorescence Features and Synthesis of Diarylethene Type Naphthalimide Compounds

Orhan

Narin

2020

Journal of the Turkish Chemical Society Section A: Chemistry

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The aim of the study was to synthesise novel photo-exchangeable photochromic fluorescent compounds. 3,4-Bis(3,5-dimethyl-4-pyrazolyl)-N-butyl-1,8-naphthalimide 6 and 3,4-bis (1,3,5trimethyl-4-pyrazolyl)-N-butyl-1,8-naphthalimide 7 naphthalimide derivative new compounds were prepared via two-step Suzuki coupling reaction of pyrazolylboronic acid esters from N-butyl-4-bromo-3-iodo-1,8-naphthalimide and characterized by 1 H-NMR, 13 C-NMR, MS and FTIR. Their photochromic fluorescence properties were investigated. Additionally, a solvent effect on the fluorescent properties of 6 and 7 was investigated. Increase of organic solvent polarity results in a red shift (to longer wavelengths) of the fluorescence emissions.

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Section: Introductionmentioning

confidence: 99%

Investigation of Photochromic Fluorescence Features and Synthesis of Diarylethene Type Naphthalimide Compounds

Orhan

Narin

2020

Journal of the Turkish Chemical Society Section A: Chemistry

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“…Photochromic fluorescence diarylethers can be used to fabricate many light-sensitive materials. The diarylethenes can be considered promising because of their advantages such as two alternating photochromism, rapid reaction, high quantum yield, fatigue resistance, large variations in the absorption wavelength between the two isomers (15)(16)(17)(18)(19).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Diarylethenes Bearing Naphthalimide Moiety and Photochromic Fluorescence Behaviors

Orhan

2017

Journal of the Turkish Chemical Society, Section A: Chemistry

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The objective of the research was to synthesize new photo-switchable photochromic fluorescence compounds. Starting from N-butyl-4-bromo-3-iodo-1,8naphthalimide, new compounds, namely 3,4-bis(2-phenyl-5-methyl-4-thiazolyl)-N-butyl-1,8-naphthalimide 1O and 3,4-bis(3,5-dimethyl-4-isoxazolyl)-N-butyl-1,8-naphthalimide 2O were prepared via two-step Suzuki coupling reaction of aryl boronic acid and esters, and their photochromic fluorescence properties were investigated. Although all prepared bisaryl naphthylimides fluoresce due to the naphthylimide moiety, among them photochrome 1O displayed photochromism. On exposure to ultraviolet light, the photochrome 1O showed a pale yellow to blue-green color change due to the formation of ring closed form 1C, which reversed to the ring opened form 1O on exposure to visible light. Conversion ratio and quantum efficiency (from O to C form) for 1O were also determined. Additionally, a solvent effect on the fluorescence properties of 1O and 2O was investigated. Increase of solvent polarity results in a red shift (to longer wavelengths) of the fluorescence emissions.

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Redox Switching of Orthoquinone‐Containing Aromatic Compounds with Hydrogen and Oxygen Gas

et al. 2016

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Unique redox switching of orthoquinone-containing pentacyclic aromatic compounds with molecular hydrogen and oxygen in the presence of ap alladium nanoparticle catalyst (SAPd) is disclosed. These molecules were predicted by in silico screening before synthesis.E fficient protocols for the synthesis of orthoquinone-containing aromatic compounds by palladium-mediated homocoupling and the benzoin condensation reaction were developed. Clear switching between orthoquinone and aromatic hydroquinone compounds was observed on the basis of their photoluminescence properties. Furthermore,the twist strain of the orthoquinone moiety could induce dramatic changes in color and emission.Highly conjugated polyaromatic compounds have been widely applied in the development of fluorescent materials, semiconductor materials,o rganic electroluminescence devices,a nd organic solar-cell devices.F or this purpose,awide variety of polyaromatic organic compounds have been designed. Va rious switching technologies of the p-conjugated molecules have also been reported, such as photochromism, [1] thermochromism, [1] electrochromism, [2] piezochromism, [3] solvatochromism, [4] and halochromism, [5] as well as redoxmediated chromism induced by electricity [2] or chemical reagents.[6] Thekey issue for the design of molecules exhibiting redox switching is the introduction of functional groups that enable interconversion between the oxidized and reduced states (OFF and ON). We were convinced that aromatic compounds containing an orthoquinone moiety were interesting candidates for redox switching,b ecause the orthoquinone could be reduced to the corresponding hydroquinone,and the hydroquinone could also be quickly oxidized to the quinone (Scheme 1).[7] Thus,two different states of a pconjugated system could be produced by aredox reaction. For the establishment of ar edox system, usually oxidizing and reducing reagents,s uch as 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), NaBH 4 ,and Na 2 S 2 O 3 ,are required.[6] However,t he side products derived from these reagents are potential problems for areversible redox system. Foraclean and reversible redox system, molecular hydrogen and oxygen would be ideal reagents.T hus,g aseous hydrogen could be used for the hydrogenation of the orthoquinone to the hydroquinone in the presence of ametal catalyst. In contrast, gaseous oxygen could be used for the oxidation of the hydroquinone to the orthoquinone. [8] In this proposed environmentally friendly redox system based on molecular hydrogen and oxygen, the main side product is removable water, and this system could be made reversible without purification. Furthermore,t his technology could possibly be applied to the development of photoluminescent materials that respond to switching between hydrogen and oxygen gas or to gas sensors for the detection of hydrogen and/or oxygen by the monitoring of fluorescence.T oo ur knowledge,o nly one example of the redox switching of acoumarin derivative as an optical material has been reported, for which ac om...

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Intermolecular hydrogen bonding-assisted high contrast fluorescent switch in the solid state

Cited by 10 publications

References 40 publications

Investigation of Photochromic Fluorescence Features and Synthesis of Diarylethene Type Naphthalimide Compounds

Investigation of Photochromic Fluorescence Features and Synthesis of Diarylethene Type Naphthalimide Compounds

Synthesis of Novel Diarylethenes Bearing Naphthalimide Moiety and Photochromic Fluorescence Behaviors

Redox Switching of Orthoquinone‐Containing Aromatic Compounds with Hydrogen and Oxygen Gas

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