Novel sugar-based azo dyes as multistimuli responsive supramolecular gelators and chemosensors

Recently Developed Carbohydrate Based Gelators and Their Applications

“…aryl azo moieties for photo-responsiveness and hydroxyl groups as pH and metal ion responsive groups [112]. The gels formed by the sugar azobenzene derivatives were found to collapse within 30 min of exposure to 254 nm and 360 nm UV light.…”

Insights into a novel class of azobenzenes incorporating 4,6-O-protected sugars as photo-responsive organogelators

“…From 13 C NMR analysis of compounds (5-7, 9-11 & 13-15) the methyl carbon atoms of the acetyl group appear in the range of 22.1-29.6 ppm. 107.0 ppm corresponds to acetal carbon of ethylidene, benzylidene and butylidene derivatives, respectively.…”

“…1 Representative examples of sugar-based low molecular weight organogelators reported in the literature. 1,13 azobenzene, 20 stilbene, 21 butadiene, 22 dithienylethene, 23 spiropyran, 24 and anthracene groups 25 are extensively incorporated to from photo-responsive materials. Similarly, the introduction of the p-methoxy group to the benzylidene acetal affects the gelation property.…”

“…Compound, 14 was obtained by the reaction of 2-acetamido-2 00 -amino-ortho-bisazobenzene, 12 (0.52 mmol, 1.04 g) and 4,6-O-ethylidene-b-D-glucopyranose 1b (0.5 mmol, 0.5 g) as a red solid. Yield: 1.00 g (76%); mp 152-154 C; 1 H NMR (CDCl 3 + DMSO-d 6 , 300 MHz), d 8.65 (d, J ¼ 8.1 Hz, 2H, Ar-H), 7.76-7.93 (m, 3H, Ar-H), 7.60 (t, J ¼ 7.5 Hz, 1H, Ar-H), 7.54 (t, J ¼ 6.3 Hz, 1H, Ar-H), 7.21-7.35 (m, 2H, Ar-H), 6.97 (d, J ¼ 8.7 Hz, 1H, Ar-H), 6.71-6.91 (m, 2H, Ar-H), 6.16 (s, 1H, -NH), 5.16 (s, 1H, Ace-H), 4.71-4.76 (q, J ¼ 4.8 Hz, 1H, Ano-H), 4.41 (s, 1H, -NH), 4.61 (s, 3H, Sac-H), 4.02-4.12 (m, 1H, Sac-H), 3.83-3.89 (q, J ¼ 4.2 Hz, 2H, Sac-OH), 3.46-3.54 (m, 1H, Sac-H), 3.21-3.32 (m, 1H, Sac-H), 1.88 (s, 3H, -NHCOCH3 ), 1.37 (t, J ¼ 4.8 Hz, 3H, Sac-CH 3 ) 13. C NMR (CDCl 3 + DMSO-d 6 , 75 MHz)d 174.2, 152.3, 147.7, 142.6, 140.3, 138.4, 136.3 (2C), 134.8, 132.4 (2C), 128.0 (2C), 125.5, 124.0, 123.2, 118.5 (2C), 104.1, 102.2, 97.8, 85.6, 80.8, 78.2, 73.3, 66.8, 29.5, 25.1.…”

A Schiff-Base Modified Pt Nano-Catalyst for Highly Efficient Synthesis of Aromatic Azo Compounds

“…Aromatic azo compounds (Aazo) are important raw materials, which are widely used in the fields of pigments [1][2][3], radical reaction initiators [4][5][6], food additives [7,8], electronic devices [9][10][11][12], and drugs [13][14][15][16]. The industrial production of Aazo is achieved by the azo-coupling reaction between a diazonium salt and an electron-rich arene, in which stoichiometric amounts of nitrite salts are used, therefore generating large amounts of dangerous wastes of diazonium salts in this process [17][18][19].…”