210
M. Rahimizadeh, M. Pordel, M. Ranaei, and M. Bakavoli
Vol 49
Figure 2. Emission spectrum of compounds 3a–e in dilute (1 ꢂ 10ꢀ6
M) chloroform solution. [Color figure can be viewed in the online
issue, which is available at wileyonlinelibrary.com.]
Figure 1. Visible absorption spectrum of compounds 3a–e in dilute (1
ꢂ 10ꢀ5 M) chloroform solution. [Color figure can be viewed in the
online issue, which is available at wileyonlinelibrary.com.]
Table 1
Photophysical data for absorption (abs) and fluorescence (flu) of 3a-e.
Dye
3a
3b
3c
3d
3e
kmax (nm)a
382, 446, 476
2.74, 1.48, 2.03
382, 446, 474
3.15, 1.68, 2.32
382, 446, 474
3.71, 1.91, 2.72
382, 446, 476
2.94, 1.48, 1.51
382, 444, 472
3.92, 2.07, 2.80
e ꢂ 10ꢀ4 (Mꢀ1 cmꢀ1 b
)
kex (nm)c
283
485
0.59
283
490
0.63
283
490
0.65
283
490
0.66
283
485
0.60
kflu (nm)d
e
UF
a Wavelengths of maximum absorbance (kmax).
b Molar extinction coefficient.
c Wavelengths of fluorescence excitation (kex).
d Wavelengths of fluorescence emission (kflu).
e Fluorescence quantum yield (UF).
NMR (CDCl3, ppm): d 1.02 (t, J ¼ 7.2 Hz, 3H, CH3), 1.81–
2.16 (m, 2H, ACH2A), 4.58 (t, J ¼ 7.2 Hz, 2H, ACH2A),
7.00 (dd, J ¼ 7.8 Hz, J0¼ 6.6 Hz, 1H, pyridine), 7.38–7.88
(m, 5H, phenyl and pyridine protons), 8.68 (d, J ¼ 7.0 Hz,
1H, pyridine), 8.9 (d, J ¼ 8.4 Hz, 1H, pyridine) ppm; 13C
NMR (CDCl3, ppm): d 10.55, 24.78, 39.38, 100.13, 109.38,
111.27, 115.19, 116.94, 118.27, 118.74, 120.48, 122.61,
124.62, 128.58, 130.97, 132.07, 139.59, 140.62, 146.95,
148.43 ppm; IR (KBr disk): m 2240 cmꢀ1 (CN). MS (m/z) 325
(Mþ). Anal. Calcd. for C15H8N4 (325.4): C, 73.83; H, 4.65; N,
21.52. Found: C, 73.41; H, 4.50; N, 21.71.
139.59, 140.62, 146.97, 148.43 ppm; IR (KBr disk): m 2240
cmꢀ1 (CN). MS (m/z) 339 (Mþ). Anal. Calcd. for C15H8N4
(339.4): C, 74.32; H, 5.05; N, 20.63. Found: C, 73.91; H,
5.15; N, 20.71.
5-Benzyl-5H-pyrido[100,200:10,20]imidazo[40,50:5,6]pyrido[2,3-b]
indole-13-carbonitrile (3e). Compound 3e was obtained as
1
shiny yellow needles (EtOH), yield (75%), mp 276–278ꢁC; H
NMR (CDCl3, ppm): d 5.80 (s, 2H, ACH2A), 7.05 (dd, J ¼
7.9 Hz, J0 ¼ 6.7 Hz, 1H, pyridine), 7.3–7.9 (m, 10H, phenyl
and pyridine protons), 8.65 (d, J ¼ 6.9 Hz, 1H, pyridine), 8.88
(d, J ¼ 8.4 Hz, 1H, pyridine) ppm; 13C NMR (CDCl3, ppm): d
49.35, 101.07, 109.31, 111.40, 115.18, 116.87, 118.23, 118.69,
120.53, 122.62, 123.76, 124.61, 124.78, 125.03, 125.81,
128.59, 130.99, 132.07, 139.58, 140.62, 146.53, 148.43 ppm;
IR (KBr disk): m 2240 cmꢀ1 (CN). Anal. Calcd. for C15H8N4
(373.4): C, 77.20; H, 4.05; N, 18.75. Found: C, 77.41; H,
4.20; N, 18.51.
5-Butyl-5H-pyrido[100,200:10,20]imidazo[40,50:5,6]pyrido[2,3-b]
indole-13-carbonitrile (3d). Compound 3d was obtained as
1
shiny yellow needles (EtOH), yield (67%), mp 232–235ꢁC; H
NMR (CDCl3, ppm): d 1.00 (t, J ¼ 6.7 Hz, 3H, CH3), 1.16–
1.51 (m, 2H, ACH2A), 1.75–2.01 (m, 2H, ACH2A), 4.59 (t, J
¼ 6.7 Hz, 2H, ACH2A), 6.96 (dd, J ¼ 7.8 Hz, J0¼ 6.6 Hz,
1H, pyridine), 7.26–7.90 (m, 5H, phenyl and pyridine protons),
8.58 (d, J ¼ 7.0 Hz, 1H, pyridine), 8.8 (d, J ¼ 8.4 Hz, 1H,
pyridine) ppm; 13C NMR (CDCl3, ppm): d 13.94, 18.65,
33.45, 38.48, 100.08, 109.38, 111.27, 115.19, 116.94, 118.27,
118.74, 120.48, 122.61, 124.62, 128.58, 130.97, 132.07,
REFERENCES AND NOTES
[1] Mꢀakosza, M. Pol J Chem 1992, 66, 3.
[2] Mꢀakosza, M. Russ Chem Bull 1996, 45, 491.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet