Synthesis of (perfluoroalkylsulfonyl)benzenes

Joglekar, Bharati; Miyake, Tomoko; Kawase, Ritsu; Shibata, Katsuyoshi; Muramatsu, Hiroshige; Matsui, Masaki

doi:10.1016/0022-1139(95)03261-b

Cited by 17 publications

(8 citation statements)

References 3 publications

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“…The diazotization-coupling reaction of 4-(perfluorobutylsulfonyl)aniline 1, obtained as described in our paper, 15 with 1-naphthylamine gave azo intermediate 2 in moderate yield. By using acetone-ethanol-water system as the reaction medium, disazo dye 3 was obtained in 30% yield.…”

Section: Resultsmentioning

confidence: 99%

Second-Order Optical Nonlinearity of Novel Methacrylate Polymer with Pendant Disazo Dye Chromophore Containing a Perfluorobutylsulfonyl Group

Joglekar

Shibata

Muramatsu

et al. 1997

Polym J

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KEY WORDSNonlinear Optics (NLO) / Second-Order Nonlinear Optical Coefficient (d33) / Second Harmonic Generation (SHG) / Perfluorobutylsulfonyl / Disazo Dye / Relaxation Behavior / Potential applications like optical communications and electrooptics have motivated researchers to flourish the area of nonlinear optics (NLO). 1 -4 To get a large second-order nonlinear optical coefficient (d 33 ), dyes terminated with strong electron-withdrawing and donating groups at both the ends of the molecule separated by a n-electron conjugated system find better position. 5 -9 Efforts are also being made to improve the relaxation behavior of the chromophore after poling. The strong electron-withdrawing nature of the perfluorobutylsulfonyl group has been reported in chromophore design for NLO. 10 -12 In our previous report, 13 disazo dyes having a perfluorobutylsulfonyl group doped in polycarbonate (PC) and poly(methyl methacrylate) (PMMA) exhibited a large d 33 value and slow relaxation behavior.Based on these results, in this note, we wish to report second-order optical nonlinearity of novel methacrylate polymer with pendant perfluorobutylsulfonyl-substituted naphthylene disazo dye. EXPERIMENTAL Preparations 4-[ 4-(Perfluorobutylsulf onyl)phenylazo ]-1-naphthylamine (2)To an 20ml acetone-water solution containing 750 mg (2 mmol) of 4-(perfluorobutylsulfonyl)aniline 1 was added cone. hydrochloric acid (0.5 ml, 6 mmol). After cooling the solution to 0°C, an aqueous solution (5 ml) of sodium nitrite (138 mg, 2 mmol) was added and stirred for 2 h. To this mixture was added an aqueous buffer solution of acetic acid-sodium acetate of 1-naphthylamine (284 mg, 2 mmol) and stirred for 2 hat -5°C. After the reaction was completed, the resulting precipitate was filtered, rinsed with water and dried. The obtained solid was purified by column chromatography (silica gel, CH2Cl 2 ), followed by recrystallization from chloroform-hexane. Yield 50%; mp 114-115°C; 1 H NMR (CDC1 3 ): fJ 4.92 (brs, 2H), 6.86 (d, J=8.2Hz, lH), lH), lH), 7.84 (d, J= 9.4Hz, lH), 8.06 (d, J=9.4Hz, lH), 8.16 (d, J=6.7Hz, t To whom correspondence should be addressed. 4-[ 4-[ 4-(Perfluorobutylsulfonyl)phenylazo ]naphthylazo ]-N-ethyl-N-hydroxyethylaniline (3)To an acetone-ethanol-water solution (2.0: 1.0: 0.5, 30ml) of 529mg of 2 (1 mmol) was added cone. hydrochloric acid (0.25 ml, 3 mmol). After cooling the solution between O and 5°C, an aqueous solution (5 ml) of sodium nitrite (69mg, 1 mmol) was added and stirred for 6 h. To this mixture was added an acetone solution (5 ml) of 2-(N-ethylanilino )ethanol (350 mg, 2 mmol) and stirred overnight at room temperature. After the reaction was completed, the resulting precipitate was washed with water and dried. The product was purified by column chromatography (silica gel, CH 2 Cl 2 ), followed by recrystallization from chloroform-hexane. Yield 30%; mp 130°C; 1 H NMR (CDC1 3 ): fJ 1.29 (t, J=6.4Hz, 3H), 1.63 (br, lH), 3.60 (q, J=6.4Hz, 2H), 3.66 (t, J=4.6Hz, 2H), 3.91 (t, J=4.6Hz, 2H), 6.87 (d, J=7.9Hz, 2H), 2H), 7.8...

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Section: Resultsmentioning

confidence: 99%

Second-Order Optical Nonlinearity of Novel Methacrylate Polymer with Pendant Disazo Dye Chromophore Containing a Perfluorobutylsulfonyl Group

Joglekar

Shibata

Muramatsu

et al. 1997

Polym J

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“…Although 4-nitrothiophenol is a very poor substrate (see section 4.1.1. and Table 11 ), it reacts with perfluoroalkyl iodides to afford 4-perfluoroalkylsulfanylnitrobenzenes in presence of NaH in DMF in almost quantitative yields [ 201 ], presumably via “hydride” catalysis.…”

Section: Reviewmentioning

confidence: 99%

Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation

Boiko¹

2010

Beilstein J. Org. Chem.

263

119

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SummaryThis review covers all of the common methods for the syntheses of aromatic and heterocyclic perfluoroalkyl sulfides, a class of compounds which is finding increasing application as starting materials for the preparation of agrochemicals, pharmaceutical products and, more generally, fine chemicals. A systematic approach is taken depending on the mode of incorporation of the SRF groups and also on the type of reagents used.

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“…The physical and spectral data of the products are given below. (16), 99 (18), 76 (30), 72 (34). (20), 99 (40), 72 (53).…”

Section: Synthesis Of Azo Dyes 3 3ј and 4-9mentioning

confidence: 99%

“…(14), 120 (17). (16), 325 (17), 226 (20), 102 (37), 72 (32). 3), 3.55-3.82 (8H, m), 7.51 (1H, t, J 7.9), 7.58 (1H, d, J 9.2), 7.67 (1H, t, J 7.9), 8.52 (1H, d, J 9.2), 9.00 (1H, d, J 7.9), 9.01 (1H, d, J 7.9); m/z 524 (M + ; 100%), 494 (15), 226 (18), 116 (21), 99 (30), 72 (45).…”

Section: Synthesis Of Azo Dyes 3 3ј and 4-9mentioning

confidence: 99%

Synthesis, structure, and UV–VIS absorption spectra of azo dyes derived from (dialkylamino)thiazole dimers †

Kim

Funabiki

Muramatsu

et al. 2001

J. Chem. Soc., Perkin Trans. 2

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published as an Advance Article on the web 16th February 2001(Dialkylamino)thiazole dimers act as very strong electron-donating coupling components in azo dyes, the first and second UV-VIS absorption bands of which were observed at λ = 568-737 (ε = 24000-88000) and 404-475 (ε = 9200-52000) nm in dichloromethane, respectively. The azo compounds derived from the (dialkylamino)thiazole dimers having very strong electron-withdrawing moieties such as 4-(perfluoroalkylsulfonyl)phenyls, 2,4-dinitrophenyl, and thiazol-2-yls exhibited a negative solvatochromism. This is the first example of a negative solvatochromism in neutral azo dyes.

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Synthesis of (perfluoroalkylsulfonyl)benzenes

Cited by 17 publications

References 3 publications

Second-Order Optical Nonlinearity of Novel Methacrylate Polymer with Pendant Disazo Dye Chromophore Containing a Perfluorobutylsulfonyl Group

Second-Order Optical Nonlinearity of Novel Methacrylate Polymer with Pendant Disazo Dye Chromophore Containing a Perfluorobutylsulfonyl Group

Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation

Synthesis, structure, and UV–VIS absorption spectra of azo dyes derived from (dialkylamino)thiazole dimers †

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