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W.P. Silva et al. / Journal of Molecular Liquids 307 (2020) 112944
8.7 Hz, 4J = 1.9 Hz, 1H), 8.15 (d, 3J = 8.7 Hz, 1H), 7.84 (AA′BB′, 4H), 7.52
(dd, 3J = 8.8 Hz, 4J = 3.9 Hz, 4H), 6.98 (AA′BB′, 4H), 6.88 (dd, 3J =
8.8 Hz, 4J = 3.9 Hz, 4H), 4.44 (t, 3J = 6.5 Hz, 2H), 4.06 (t, 3J = 6.4 Hz,
2H), 3.92 (d, 3J = 5.6 Hz, 2H), 3.84 (s, 6H), 1.93–1.83 (m, 4H, -CH2-),
3J = 6.7 Hz, 4H, Ar-OCH2-), 3.83 (t, 3J = 6.6 Hz, 4H, Ar-OCH2-),
1.94–1.64 (m, 12H, -CH2-), 1.59–1.06 (m, 76H, -CH2-), 0.93–0.84
(m, 12H, -CH3). 13C NMR (100 MHz, CDCl3) δ: 166.05; 161.85;
154.85; 154.20; 151.14; 150.29; 148.76; 148.72; 146.71; 143.04;
140.13; 136.06; 131.56; 131.37; 131.22; 131.00; 129.22; 124.86;
123.80; 123.03; 122.80; 115.29; 115.23; 114.74; 113.18; 113.06;
100.00; 69.21; 68.18; 31.94; 29.77; 29.72; 29.71; 29.69; 29.66;
29.48; 29.45; 29.40; 29.39; 29.24; 29.23; 29.15; 28.70; 26.04;
1.76 (m, 1H, -CH-), 1.45 (m, 10H, -CH2-), 0.98–0.89 (m, 6H, -CH3). 13
C
NMR (100 MHz, CDCl3) δ: 166.03; 161.42; 161.04; 160.56; 160.43;
154.64; 153.98; 146.98; 146.90; 143.08; 140.20; 131.56; 131.39;
131.30; 131.23; 131.04; 129.17; 129.11; 124.27; 114.68; 114.66;
114.64; 113.87; 113.84; 99.99; 70.85; 68.10; 65.45; 55.33; 39.38;
30.52; 29.41; 29.14; 29.09; 28.69; 25.94; 25.82; 23.86; 23.04; 14.07;
11.12. Q-TOF: m/z calcd for C49H54N4O6 (M + H)+: 795.4116; found:
795.4119.
25.91; 22.70; 14.12. Q-TOF: m/z calcd for C87H129ClN4O7 (M + H)+
:
1377.9623; found: 1377.9619.
4.3.2.9. (E)-6-(4-((4-methoxyphenyl)diazenyl)phenoxy)hexyl 2,3-bis(3,4-
bis(dodecyloxy)-phenyl)quinoxaline-6-carboxylate (4d). The solid was
purified by column chromatography using chloroform/hexane
(3:1) as the eluent and recrystallized in acetone. Yield: 52,89%. IV
(νmax/cm−1): 2922, 2857, 1716, 1603, 1258, 1177, 1145, 847. 1H
NMR (400 MHz, CDCl3) δ: 8.84 (s, 1H, Ar-H), 8.33 (d, 3J = 8.8 Hz,
1H), 8.15 (d, 3J = 8.6 Hz, 1H), 7.86 (AA′BB′, 4H), 7.19–6.96 (m, 8H,
Ar-H), 6.85 (d, 3J = 8.3 Hz, 2H), 4.44 (t, 3J = 6.5 Hz, 2H, Ar-
COOCH2-), 4.09–3.97 (m, 6H, Ar-OCH2-), 3.88–3.79 (m, 7H, Ar-
OCH3 e Ar-OCH2-), 1.96–1.68 (m,12H, -CH2-), 1.49–1.17 (m, 76H,
-CH2-), 0.86 (m, -CH3, 12H). 13C NMR (100 MHz, CDCl3) δ: 165.95;
162.75; 155.97; 154.76; 154.11; 150.25; 150.09; 148.69; 148.65;
148.12; 146.73; 142.96; 140.03; 131.46; 131.29; 131.12; 130.90;
129.08; 128.99; 125.51; 124.58; 122.99; 122.97; 122.94; 122.73;
115.2; 115.20; 114.82; 113.12; 112.99; 69.15; 69.10; 68.22; 65.30;
31.85; 29.71; 29.67; 29.61; 29.59; 29.57; 29.53; 29.38; 29.35;
29.30; 29.29; 29.14; 29.07; 28.96; 28.60; 25.95; 25.79; 25.69;
22.63; 22.62; 22.60; 22.58; 22.57; 14.02. Q-TOF: m/z calcd for
4.3.2.6. (E)-6-(4-((4-(decyloxy)phenyl)diazenyl)phenoxy)hexyl 2,3-bis
(3,4-bis(dodecyloxy)-phenyl)quinoxaline-6-carboxylate (4a). The solid
was purified by column chromatography using a gradient of hexane/
ethyl acetate (5:1) and chloroform/hexane (3:1) as the eluent and re-
crystallized in butyl alcohol. Yield: 52,9%. IV (νmax/cm−1): 2922, 2849,
1716, 1603, 1515, 1242, 1145, 1016, 855. 1H NMR (400 MHz, CDCl3) δ:
8.86 (d, 4J = 1.9 Hz, 1H), 8.33 (dd, 3J = 8.7 Hz, 4J = 1.9 Hz, 1H), 8.17
(d, 3J = 8.2 Hz, 1HH), 7.86 (AA′BB′, 4H), 7.15 (dt, 3J = 8.3 Hz, 4J =
2.2 Hz), 7.09 (dd, 3J = 11.6 Hz, 4J = 2.1 Hz, 2H), 6.99 (AA′BB′, 4H),
6.85 (m, 2H), 4.45 (t, 3J = 6.5 Hz, 2H), 4.07–3.99 (m, 8H, Ar-O-CH2-),
3.83 (t, 3J = 6.7 Hz, 4H, Ar-O-CH2-), 1.94–1.78 (m, 12H, -CH2-),
1.76–1.70 (m, 4H, CH2), 1.38–1.21 (m, 90H, -CH2-), 0.92–0.86 (m,
15H, -CH3). 13C NMR (100 MHz, CDCl3) δ: 166.04; 161.16; 161.05;
154.83; 154.18; 150.27; 150.13; 148.74; 148.73; 146.98; 146.92;
143.03; 140.13; 131.55; 131.37; 131.24; 131.01; 129.15; 129.09;
124.28; 123.02; 122.81; 115.31; 115.28; 114.64; 114.33; 113.19;
113.08; 69.20; 68.33; 68.10; 65.45; 64.44; 31.93; 31.89; 29.76; 29.70;
29.68; 29.65; 29.57; 29.55; 29.47; 29.43; 29.39; 29.37; 29.31; 29.22;
29.15; 28.70; 26.03; 25.93; 25.83; 25.36; 22.69; 14.11. Q-TOF: m/z
calcd for C97H150N4O8 (M + H)+: 1501.1559; found: 1501.1560.
C
88H132N4O8 (M + H)+: 1374.01179; found: 1374.01178.
4.3.2.10. (E)-6-(4-((4-((2-ethylhexyl)oxy)phenyl)diazenyl)phenoxy)
hexyl 2,3-bis(3,4-bis(dodecy-loxy)phenyl)quinoxaline-6-carboxylate
(4e). The solid was purified by column chromatography using a gra-
dient of hexane/ethyl acetate (5:1) and chloroform/hexane (3:1) as
the eluent and recrystallized in butyl alcohol. Yield: 41,9%. IV
(νmax/cm−1): 2922, 2849, 1716, 1603, 1242, 1137, 1032, 839. 1H
NMR (400 MHz, CDCl3) δ: 8.85 (d, 4J = 1.6 Hz, 1H, Ar-H), 8.32 (dd,
3J = 8.8 Hz, 4J = 1.8 Hz, 1H), 8.16 (d, 3J = 8.7 Hz, 1H), 7.85 (AA′BB
′, 4H), 7.14 (d, 3J = 8.3 Hz, 2H), 7.08 (d, 3J = 8.5 Hz, 2H), 7.01 (AA′
BB′, 4H), 6.84 (dd, 3J = 8.4, 4J = 6.1 Hz, 2H), 4.44 (t, 3J = 6.4 Hz,
2H, Ar-COOCH2-), 4.09–3.98 (m, 6H, Ar-OCH2-), 3.92 (d, 3J =
5.7 Hz, 2H, OCH2CH-), 3.82 (t, 3J = 6.6 Hz, 4H, Ar-OCH2), 1.97–1.62
(m, 13H, -CH2-), 1.64–1.10 (m, 88H, -CH2-), 1.00–0.81 (m, 18H,
-CH3). 13C NMR (100 MHz, CDCl3) δ: 166.04; 161.42; 161.04;
154.83; 154.18; 150.27; 150.13; 148.75; 146.99; 146.88; 143.03;
140.13; 131.55; 131.02; 129.15; 124.27; 123.02; 115.29; 114.67;
114.64; 113.08; 111.54; 70.84; 69.20; 68.10; 65.45; 39.38; 31.93;
30.52; 29.76; 29.70; 29.68; 29.65; 29.47; 29.44; 29.39; 29.37;
29.22; 29.15; 29.09; 28.71; 26.03; 25.93; 25.83; 23.86; 23.04;
4.3.2.7. (E)-6-(4-((4-nitrophenyl)diazenyl)phenoxy)hexyl 2,3-bis(3,4-bis
(dodecyloxy)-phenyl)quinoxaline-6-carboxylate (4b). The solid was puri-
fied by column chromatography using chloroform/hexane (3:1) as the
eluent and recrystallized in acetone. Yield: 62,1%. IV (νmax/cm−1):
2922, 2849, 1724, 1595, 1523, 1346, 1258, 1145, 863. 1H NMR
(400 MHz, CDCl3) δ: 8.85 (d, 4J = 1.8 Hz, 1H), 8.41–8.27 (m, 3H, Ar-
H), 8.16 (d, 3J = 8.5 Hz, 1H), 7.95 (AA′BB′, 4H), 7.14 (dt, 3J = 8.3 Hz,
4J = 2.1 Hz, 2H), 7.08 (dd, 3J = 9.3 Hz, 4J = 2.0 Hz, 2H), 7.02 (AA′BB′,
2H), 6.84 (d, 3J = 8.3 Hz, 2H), 4.44 (t, 3J = 6.4 Hz, 2H, -COOCH2-),
4.10 (t, 3J = 6.3 Hz, 2H, Ar- OCH2), 4.00 (t, 3J = 6.7 Hz, 4H, Ar-OCH2-),
3.82 (t, 3J = 6.5 Hz, 4H), 1.94–1.67 (m, 12H, -CH2-), 1.46–1.17 (m,
76H, -CH2-), 0.91–0.84 (m, 12H, -CH3). 13C NMR (100 MHz, CDCl3) δ:
166.03; 162.83; 156.05; 154.84; 154.20; 150.33; 150.17; 148.77;
148.73; 148.20; 146.82; 143.04; 140.12; 131.55; 131.37; 131.21;
130.98; 129.17; 129.07; 125.59; 124.67; 123.07; 123.05; 123.03;
122.81; 115.35; 115.29; 114.90; 113.20; 113.07; 69.23; 68.30; 65.38;
31.93; 29.80; 29.75; 29.71; 29.70; 29.67; 29.65; 29.62; 29.47; 29.43;
29.38; 29.37; 29.23; 29.22; 29.15; 29.05; 28.69; 26.03; 25.88; 25.77;
22.72; 22.70; 22.69; 22.67; 22.65; 14.10. Q-TOF: m/z calcd for
22.69; 14.11; 11.12. Q-TOF: m/z calcd for C95H146N4O8 (M + H)+
1473.1247; found: 1473.1251.
:
C
87H129N5O9 (M + H)+: 1388.9863; found: 1388.9857.
CRediT authorship contribution statement
4.3.2.8. (E)-6-(4-((4-chlorophenyl)diazenyl)phenoxy)hexyl 2,3-bis(3,4-
bis(dodecyloxy)phenyl)-quinoxaline-6-carboxylate (4c). The solid was
purified by column chromatography using chloroform/hexane
(3:1) as the eluent and recrystallized in isopropyl alcohol. Yield:
55,3%. IV (νmax/cm−1): 2922, 2849, 1716, 1603, 1258, 1185, 1137,
839. 1H NMR (400 MHz, CDCl3) δ: 8.86 (d, 4J = 1.8 Hz, 1H), 8.33
(dd, 3J = 8.8 Hz, 4J = 1.8 Hz, 1H), 8.17 (d, 3J = 8.5 Hz, 1H), 7.89
(AA′BB′, 2H), 7.83 (AA′BB′, 2H), 7.47 (AA′BB′, 2H), 7.15 (dt, 3J =
8.1 Hz, 4J = 1.9 Hz, 2H), 7.09 (dd, 3J = 11.3, 4J = 2.0 Hz, 2H), 7.00
(AA′BB′, 2H), 6.86 (dt, 3J = 8.3, 4J = 1.9 Hz, 2H), 4.45 (t, 3J =
6.4 Hz, 2H, -COOCH2-), 4.08 (t, 3J = 6.3 Hz, 2H, Ar-OCH2-), 4.01 (t,
Welisson P. Silva: Data curation, Formal analysis, Investigation,
Methodology, Writing - original draft, Writing - review & editing.
Edivandro Girotto: Data curation, Formal analysis, Investigation, Meth-
odology. Hugo Gallardo: Funding acquisition, Supervision, Project ad-
ministration. Rodrigo Cristiano: Formal analysis, Investigation,
Supervision, Funding acquisition, Project administration, Writing - orig-
inal draft, Writing - review & editing.
Declaration of competing interest
No conflicts of interest.