Articles
16 Hz, Olifenic H), 6.90 (d, 3H, J=8.4 Hz, Ar), 4.08 (m, 12H, 6ꢂ
OCH2), 2.17-1.30 (m, 96H, 48ꢂCH2) and 0.90 (t, 18H, 6ꢂCH3);
13C NMR(100 MHz): 171.13, 149.71, 149.4, 141.79, 135.08, 130.67,
130.20, 129.38, 126.41, 126.03, 120.56, 113.76, 111.87, 69.49, 69.33,
31.96, 29.64, 29.48, 29.40, 26.12, 22.72 and 14.13; Anal. calcd for
29.63, 29.49, 29.46, 29.39, 29.32, 26.15, 22.70 and 14.10; Anal. calcd
for C126H195N3O9: C, 79.82; H, 10.37; N, 2.22. Found: C, 80.15; H,
10.07; N, 2.42.
TTz-10: Rf =0.52 (5% EtOAc-hexane); a yellow solid; yield: 0.42 g
(72%); IR (KBr pellet): nmax in cmꢀ1 2923, 2853, 1603, 1578, 1503,
1467 and 1371; UV-Vis: l max =378.4 nm (absorption) and 541.4 nm
C
105H153N3O6: C, 80.19; H, 9.93; N, 2.71. Found: C, 80.58; H, 9.75; N,
2.60.
(emission), e1 =10.67ꢂ104 L mol ꢀ1 cmꢀ1
,
e2 =2.97ꢂ104 L mol
TTz-6: Rf =0.53 (5% EtOAc-hexane); a yellow solid; yield: 0.35 g
(80%); IR (KBr pellet): nmax in cmꢀ1 2931, 2859, 1604, 1579, 1505,
ꢀ1 cmꢀ1
;
1H NMR (400 MHz): d 8.78 (d, 6H, J=8.5 Hz, Ar), 7.70 (d,
6H, J=8.5 Hz, Ar), 7.20 (d, 3H, J=16 Hz, olifenic H), 7.11 (d, 3H, J=
16.4 Hz, olifenic H), 6.78 (s, 6H, Ar), 4.07 (t, 12H, J=6.5 Hz, 6ꢂ
OCH2), 4.02 (t, 6H, J=6.6 Hz, 3ꢂOCH2), 1.88-1.75 (m, 18H, 9ꢂCH2)
and 1.54-0.87 (m, 153H, 63ꢂCH2, 9ꢂCH3); 13C NMR(100 MHz):
171.16, 153.40, 141.57, 138.86, 135.24, 132.18, 130.97, 129.38,
127.07, 126.54, 105.59, 73.59, 69.29, 31.93, 30.37, 29.67, 29.62,
29.45, 26.15, 22.69 and 14.10; Anal. calcd for C135H213N3O9: C, 80.18;
H, 10.62; N, 2.08. Found: C, 80.48; H, 10.48; N, 1. 69.
1469 and 1372; UV-Vis:
l max =378.04 nm (absorption) and
544.57 nm (emission), e1 =16.96ꢂ104 L mol ꢀ1 cmꢀ1, e2 =4.81ꢂ
1
104 L mol ꢀ1 cmꢀ1; H NMR (400 MHz): d 8.78 (d, 6H, J=8.4 Hz, Ar),
7.71 (d, 6H, J=8.4 Hz, Ar), 7.21 (d, 3H, J=16 Hz, olifenic H), 7.11
(d, 3H, J=16.4 Hz, olifenic H), 6.78 (s, 6H, Ar), 4.07 (t, 12H, J=
6.4 Hz, 6ꢂOCH2), 4.02 (t, 6H, J=6.4 Hz, 3ꢂOCH2), 1.87-1.75 (m,
18H, 9ꢂCH2) and 1.54-0.90 (m, 81H, 27ꢂCH2, 9ꢂCH3);
13C NMR(100 MHz): 171.15, 153.40, 141.56, 138.87, 135.24, 132.18,
130.97, 129.38, 127.07, 126.54, 105.60, 73.58, 69.29, 69.20, 53.39,
31.79, 31.61, 30.32, 29.44, 25.81, 25.79, 22.69, 22.65 and 14.08;
Anal. calcd. for C99H141N3O9: C, 78.37; H, 9.37; N, 2.77. Found: C,
78.56; H, 9.29; N, 2.89.
TTz-11: Rf =0.53 (5% EtOAc-hexane); a yellow solid; yield: 0.48 g
(78%); IR (KBr pellet): nmax in cmꢀ1 2920, 2851, 1603, 1579, 1509,
1467 and 1370; UV-Vis: l max =378.4 nm (absorption) and 557.1 nm
(emission), e1 =5.43ꢂ104 L mol ꢀ1 cmꢀ1
,
e2 =1.52ꢂ104 L mol
ꢀ1 cmꢀ1; H NMR (400 MHz): d 8.77 (d, 6H, J=8 Hz, Ar), 7.70 (d, 6H,
J=8.4 Hz, Ar), 7.20 (d, 3H, J=16 Hz, olifenic H), 7.10 (d, 3H, J=
16 Hz, olifenic H), 6.78 (s, 6H, Ar), 4.07 (t, 12H, J=6.4 Hz, 6ꢂOCH2),
4.02 (t, 6H, J=6.4 Hz, 3ꢂOCH2), 1.88-1.75 (m, 18H, 9ꢂCH2) and
1.54-0.87 (m, 171H, 72ꢂCH2, 9ꢂCH3); 13C NMR(100 MHz): 171.15,
153.40, 141.56, 138.87, 135.24, 132.18, 130.97, 129.38, 127.06,
126.53, 105.60, 73.58, 69.29, 31.94, 30.38, 29.75, 29.67, 29.46, 29.38,
26.15, 22.70 and 14.11; Anal. calcd for C144H231N3O9: C, 80.50; H,
10.84; N, 1.96. Found: C, 80.24; H, 10.99; N, 1.94.
1
TTz-7: Rf =0.52 (5% EtOAc-hexane); a yellow solid; yield: 0.40 g
(83%); IR (KBr pellet): nmax in cmꢀ1 2927, 2856, 1603, 1578, 1505,
1467 and 1370; UV-Vis:
l max =378.69 nm (absorption) and
544.34 nm (emission), e1 =17.42ꢂ104 L mol ꢀ1 cmꢀ1, e2 =4.85ꢂ
1
104 L mol ꢀ1 cmꢀ1; H NMR (400 MHz): d 8.78 (d, 6H, J=12 Hz, Ar),
7.71 (d, 6H, J=12 Hz, Ar), 7.20 (d, 3H, J=16 Hz, olifenic H), 7.11 (d,
3H, J=16 Hz, olifenic H), 6.78 (s, 6H, Ar), 4.08 (t, 12H, J=8 Hz, 6ꢂ
OCH2), 4.02 (t, 6H, J=8 Hz, 3ꢂOCH2), 1.87-1.75 (m, 18H, 9ꢂCH2)
and 1.54-0.90 (m, 99H, 36ꢂCH2, 9ꢂCH3); 13C NMR(100 MHz):
172.22, 154.36, 142.44, 139.73, 136.08, 133.02, 131.78, 130.19,
127.86, 127.33, 106.26, 74.05, 69.72, 32.13, 32.05, 30.55, 29.67,
29.44, 29.28, 26.26, 22.82, 22.77 and 14.17; Anal. calcd for
C108H159N3O9: C, 78.93; H, 9.75; N, 2.56. Found: C, 79.15; H, 9.66; N,
2.65.
TTz-12: Rf =0.55 (5% EtOAc-hexane); a yellow solid; yield: 0.50 g
(76%); IR (KBr pellet): nmax in cmꢀ1 2923, 2854, 1603, 1579, 1508,
1467 and 1371; UV-Vis: l max =377.2 nm (absorption) and 538.8 nm
(emission), e1 =11.60ꢂ104 L mol ꢀ1 cmꢀ1
,
e2 =2.42ꢂ104 L mol
ꢀ1 cmꢀ1
;
1H NMR (400 MHz): d 8.77 (d, 6H, J=8.4 Hz, Ar), 7.70 (d,
6H, J=8.4 Hz, Ar), 7.20 (d, 3H, J=16 Hz, olifenic H), 7.10 (d, 3H,
J=16 Hz, olifenic H), 6.78 (s, 6H, Ar), 4.07 (t, 12H, J=6.4 Hz, 6ꢂ
OCH2), 4.02 (t, 6H, J=6.6 Hz, 3ꢂOCH2), 1.87-1.75 (m, 18H, 9ꢂCH2)
and 1.55-0.87 (m, 189H, 81ꢂCH2, 9ꢂCH3); 13C NMR(100 MHz):
171.14, 153.39, 141.55, 138.09, 135.23, 132.17, 130.96, 129.37,
127.05, 126.53, 105.58, 73.57, 69.27, 31.93, 30.37, 29.66, 29.45,
29.37, 26.14, 22.69 and 14.10; Anal. calcd for C153H249N3O9: C, 80.79;
H, 11.03; N, 1.85. Found: C, 80.43; H, 11.14; N, 1.89.
TTz-8: Rf =0.57 (5% EtOAc-hexane); a yellow solid; yield: 0.43 g
(84%); IR (KBr pellet): nmax in cmꢀ1 2922, 2852, 1603, 1579, 1505,
1467 and 1371; UV-Vis:
l max =378.5 nm (absorption) and
543.68 nm (emission), e1 =13.3ꢂ104 L mol ꢀ1 cmꢀ1, e2 =3.65ꢂ104 L
1
mol ꢀ1 cmꢀ1; H NMR (400 MHz): d 8.77 (d, 6H, J=8.4 Hz, Ar), 7.70
(d, 6H, J=8.4 Hz, Ar), 7.20 (d, 3H, J=16 Hz, olifenic H), 7.10 (d, 3H,
J=16 Hz, olifenic H), 6.78 (s, 6H, Ar), 4.07 (t, 12H, J=6.4 Hz, 6ꢂ
OCH2), 4.02 (t, 6H, J=6.4 Hz, 3ꢂOCH2), 1.88-1.74 (m, 18H, 9ꢂCH2)
and 1.55-0.88 (m, 117H, 45ꢂCH2, 9ꢂCH3); 13C NMR(100 MHz):
171.14, 153.39, 141.56, 138.86, 135.23, 132.18, 130.96, 129.37,
127.06, 126.53, 105.59, 73.58, 69.29, 31.92, 31.85, 30.89, 30.37,
29.56, 29.49, 29.40, 29.31, 26.14, 22.69 and 14.08; Anal. calcd for
C117H177N3O9: C, 79.41; H, 10.08; N, 2.37. Found: C, 80.05; H, 9.77; N,
2.54.
TTz-14: Rf =0.51 (5% EtOAc-hexane); a yellow solid; yield: 0.54 g
(74%); IR (KBr pellet): nmax in cmꢀ1 2923, 2854, 1603, 1578, 1504,
1467 and 1370; UV-Vis: l max =377.7 nm (absorption) and 542.9 nm
(emission), e1 =9.32ꢂ104 L mol ꢀ1 cmꢀ1
ꢀ1 cmꢀ1
,
e2 =2.712ꢂ104 L mol
;
1H NMR (400 MHz): d 8.78 (d, 6H, J=8.4 Hz, Ar), 7.71 (d,
6H, J=8.4 Hz, Ar), 7.20 (d, 3H, J=16 Hz, olifenic H), 7.11 (d, 3H, J=
16 Hz, olifenic H), 6.78 (s, 6H, Ar), 4.07 (t, 12H, J=8.6 Hz, 6ꢂOCH2),
3.98 (t, 6H, J=6 Hz, 3ꢂOCH2), 1.88-1.75 (m, 18H, 9ꢂCH2) and 1.55-
0.88 (m, 225H, 99ꢂCH2, 9ꢂCH3); 13C NMR(100 MHz): 171.16,
153.40, 141.57, 138.88, 135.24, 132.18, 130.97, 129.37, 127.07,
126.54, 105.61, 73.58, 69.30, 53.39, 31.94, 30.38, 29.72, 29.67, 29.63,
29.49, 29.45, 29.37, 26.14, 22.69 and 14.10; Anal. calcd for
C171H285N3O9: C, 81.27; H, 11.37; N, 1.66. Found: C, 81.41; H, 11.06;
N, 1.64.
TTz-9: Rf =0.50 (5% EtOAc-hexane); a yellow solid; yield: 0.41 g
(75%); IR (KBr pellet): nmax in cmꢀ1 2927, 2856, 1603, 1578, 1505,
1467 and 1370; UV-Vis:
l max =378.49 nm (absorption) and
543.13 nm (emission), e1 =18.39ꢂ104 L mol ꢀ1 cmꢀ1, e2 =5.06ꢂ
1
104 L mol ꢀ1 cmꢀ1; H NMR (400 MHz): d 8.78 (d, 6H, J=8.4 Hz, Ar),
7.70 (d, 6H, J=8.4 Hz, Ar), 7.20 (d, 3H, J=16 Hz, olifenic H), 7.10
(d, 3H, J=16 Hz, olifenic H), 6.78 (s, 6H, Ar), 4.04 (t, 12H, J=6.4 Hz,
6ꢂOCH2), 3.99 (t, 6H, J=6.4 Hz, 3ꢂOCH2), 1.87-1.75 (m, 18H, 9ꢂ
CH2) and 1.55-0.88 (m, 135H, 54ꢂCH2, 9ꢂCH3); 13C NMR(100 MHz):
171.15, 153.39, 141.56, 138.86, 135.23, 132.18, 130.96, 129.37,
127.06, 126.53, 105.59, 73.59, 69.29, 31.96, 31.92, 30.38, 29.70,
TTz-16: Rf =0.53 (5% EtOAc-hexane); a yellow solid; yield: 0.59 g
(74%); IR (KBr pellet): nmax in cmꢀ1 2918, 2850, 1604, 1579, 1506,
1468 and 1372; UV-Vis: l max =377.7 nm (absorption) and 542.1 nm
ChemPhysChem 2016, 17, 1 – 14
11
ꢀ 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
&
These are not the final page numbers! ÞÞ