Redox photochromism of viologen in organized solid state

Nanasawa, Masato; Matsukawa, Yasuo; Jin, Jing Ji; Haramoto, Yuichiro

doi:10.1016/s1010-6030(97)00105-6

Cited by 20 publications

(27 citation statements)

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“…These results were presumably related to the flexible n-butyl groups lined to the viologen moieties. Note here that diphenylviologens containing the long alkylbenzene sulfonates (n = 10, 13 and 15) do form SmA phases until their decomposition temperatures, that is, they do not show the isotropic transitions because of the presence of the more rigid phenyl groups attached to the viologen moieties [16,35]. The short alkylbenzenesulfonates with n = 6 and 8 do not form LC phases [16,35].…”

Section: Thermotropic Lc Properties Of 4-n-alkylbenzenesulfonic Acidsmentioning

confidence: 92%

“…Note here that diphenylviologens containing the long alkylbenzene sulfonates (n = 10, 13 and 15) do form SmA phases until their decomposition temperatures, that is, they do not show the isotropic transitions because of the presence of the more rigid phenyl groups attached to the viologen moieties [16,35]. The short alkylbenzenesulfonates with n = 6 and 8 do not form LC phases [16,35]. In addition, guanidinium alkylbezene sulfonates with even alkyl chain lengths n = 8 or higher do form smectic LC phases [34].…”

Section: Thermotropic Lc Properties Of 4-n-alkylbenzenesulfonic Acidsmentioning

confidence: 99%

“…2.5. General Procedure for the Synthesis1,1 -di-n-butyl-4,4 -bipyridinium di(4-n-alkylbenzenesulfonates) by Metathesis Reaction (V12, V14, V16, V18) Using 4-n-alkylbenzenesulfonic Acid [35] Ethanol (35 mL) was slowly added to 1,1 -di-n-butyl-4,4 -bipyridinium dibromide (0.93 g, 2.16 mmol) in a 100 mL round-bottomed flask and heated on stirring to form a clear solution. The 4-dodecylbenzenesulfonic acid (1.50 g, 4.60 mmol) was then slowly added to the hot solution, and the reaction flask was heated to reflux for 48 h. The solvent was reduced using a rotary evaporator.…”

Section: Synthesis Of 11 -Di-n-butyl-44 -Bipridinium Dibromidementioning

confidence: 99%

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Thermotropic Liquid-Crystalline Properties of Viologens Containing 4-n-alkylbenzenesulfonates

et al. 2019

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A series of viologens containing 4-n-alkylbenzenesulfonates were synthesized by the metathesis reaction of 4-n-alkylbenzenesulfonic acids or sodium 4-n-alkylbezenesulfonates with the respective viologen dibromide in alcohols. Their chemical structures were characterized by Fourier Transform Infrared, 1H and 13C Nuclear Magnetic Resonance spectra and elemental analysis. Their thermotropic liquid-crystalline (LC) properties were examined by differential scanning calorimetry and polarizing optical microscopy. They formed LC phases above their melting transitions and showed isotropic transitions. As expected, all the viologen salts had excellent stabilities in the temperature range of 278–295 °C as determined by thermogravimetric analysis.

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Section: Thermotropic Lc Properties Of 4-n-alkylbenzenesulfonic Acidsmentioning

confidence: 92%

Section: Thermotropic Lc Properties Of 4-n-alkylbenzenesulfonic Acidsmentioning

confidence: 99%

Section: Synthesis Of 11 -Di-n-butyl-44 -Bipridinium Dibromidementioning

confidence: 99%

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Thermotropic Liquid-Crystalline Properties of Viologens Containing 4-n-alkylbenzenesulfonates

et al. 2019

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“…Bis-quaternized 4,4'-bipyridinium salts (''viologens'') are well-known building blocks of special importance because they allow the generation of functional materials with a multitude of stimuli-induced chromism like electrochromism [1,2], photochromism [3,4], thermochromism [5,6], piezochromism [7], solvatochromism [8]. A particular interest for such compounds lies in their electron [9,10] or charge transfer [11,12] abilities.…”

Section: Graphical Abstract Introductionmentioning

confidence: 99%

Viologen capped by nucleobase—building blocks for functional materials: synthesis and structure–properties relationship

Ciobanu

Jordan²

2021

J Mater Sci

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The current study presents a new class of functional derivatives (1–3) consisting of a dicationic viologen (4,4’-bipyridinium unit) (V2+) capped by nucleobases thymine (NB1), adenine (NB2), thymine/adenine (NB1, NB2), and ion-paired with amphiphilic anion 3,4,5-tris(dodecyloxy)benzene sulfonate (DOBS−). The target of our work focuses on the design and synthesis of molecular building blocks in which three different functionalities are combined: chromophore (V2+ unit), molecular recognition (NB unit), and thermotropic liquid crystal (DOBS unit). The resulted materials exhibit liquid crystalline properties at ambient temperature with significant particularities-induced by nucleobases in the mesogen structure. Structure–properties relationship study focuses on providing knowledge about (1) how the thermotropic, redox properties, thermochromism, or ionic conductive properties are influenced by the presence of purinic or pyrimidinic nucleobases, and (2) how effective is their ability to self-assembly by hydrogen bonding in nonpolar solvents. The presence of nucleobases has been proved to have a substantial impact on electron transfer rate during the reduction of viologen moieties by intermolecular aggregation. Ionic conductivity and thermochromic properties of derivatives 1–3 were investigated and compared to a non-containing nucleobase analog methyl viologen with 3,4,5-tris(dodecyloxy)benzene sulfonate anion (MV) as reference. Graphical abstract

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“…Usually, the V + 9 is unstable, therefore the photogenerated V + 9 is observed within the flash-photolytic scale under anaerobic conditions, except in a weak alkali medium 5) . Previously, we have reported that, when viologen embedded in thin isotropic polymer films was irradiated by near UV, photoinduced V + 9 existed for a long time due to stabilization of the surrounding solid matrix through restriction of air oxidation and the decrease of the thermal reverse electron transfer 6,7) . Tsukahara et al have reported that the relative stabilized radicals could reduce cobalt complexes in deaerated aqueous solutions 8) .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and photoinduced coloration of ferric bipyridine complex linked viologen units in a polymer matrix

Jin

Haramoto

Nanasawa³

1999

Macromol. Rapid Commun.

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Redox photochromism of viologen in organized solid state

Cited by 20 publications

References 20 publications

Thermotropic Liquid-Crystalline Properties of Viologens Containing 4-n-alkylbenzenesulfonates

Thermotropic Liquid-Crystalline Properties of Viologens Containing 4-n-alkylbenzenesulfonates

Viologen capped by nucleobase—building blocks for functional materials: synthesis and structure–properties relationship

Synthesis and photoinduced coloration of ferric bipyridine complex linked viologen units in a polymer matrix

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