5
62
S. Ghosh and R. Manna
b
i
5
00 MHz) d: 7.23 (m, H ), 7.12 (d, J ¼ 10 Hz, H ), 6.81 (d,
oligomer solution. For fluorescence, the solution was
irradiated at the excitation wavelength of 425 nm
maintaining both the excitation and emission slits at 5.0.
nm upon addition of cations, the changes in emission and
absorbance of the oligomer solution were noted.
j
a,c
J ¼ 10 Hz, H ), 6.64 (m, H ), 4.18–4.16 (dd, J ¼ 3 Hz,
l
H ), 3.95 (m, H ), 3.57–3.50 (m, H ), 3.09 (t,
m,h
d,g
f,e
k
13
J ¼ 7.5 Hz, H ), 1.62 (s, H ). C NMR (CDCl3,
1
1
6
25 MHz) d: 156.34, 143.65, 129.55 (unresolved),
27.77, 116.41, 114.02, 111.71 (unresolved), 111.18,
8.75, 67.09, 52.23, 51.09, 44.75, 41.72, 31.02 anal. calcd
Acknowledgement
for (C H NO S ) : C, 71.44; H, 7.41; N, 1.70. Found: C,
4
9
61
6 2 n
Funding from Department of Science and Technology
7
1.61; H, 7.46; N, 1.67. GPC (using polystyrene standard
(SR/FTP/CS-88/2007), Government of India, is gratefully
acknowledged.
and THF eluent): M ¼ 1071, MWD 2.4.
w
Synthesis of 1
References
Oligomer 1a (0.086 g, 0.126 mmol) was dissolved in 1,4-
dioxan–water (3:1, v/v, 10 ml) at 08C. A diazonium salt of
(
1) (a) Boening, D.W. Chemosphere 2000, 40, 1335–1351.
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(
1
-naphthylamine was prepared by adding an aqueous
2
Sutton, D. Environ. Toxicol. 2003, 18, 149–175.
(c) Templeton, D.M. Pure Appl. Chem. 2004, 76,
1255–1268. (d) Fang, G.Z.; Tan, J.; Yan, X.P. Anal. Chem.
2
solution of NaNO2 (1.04 £ 10 g, 0.15 mmol) into a
2
2
solution of 1-naphthylamine (1.8 £ 10 g, 0.126 mmol in
2
005, 77, 1734–1739.
0
2
.002 ml acetic acid). The mixture was stirred at 08C for
min and then added dropwise into the solution of 1a. The
(
2) (a) Fitzgerald, W.F.; Lamborg, C.H.; Hammerschmidt, C.R.
Chem. Rev. 2007, 107, 641–662. (b) Xie, J.; M e´ nand, M.;
Maisonneuve, S.; M e´ tivier, R. J. Org. Chem. 2007, 72,
5980–5985. (c) Selid, P.D.; Xu, H.; Collins, E.M.;
Collins, M.S.F.; Zhao, J.X. Sensors 2009, 9, 5446–5459.
3) (a) Shiraishi, Y.; Maehara, H.; Ishizumi, K.; Hirai, T.
Org. Lett. 2007, 9, 3125–3128. (b) Nolan, E.M.; Lippard, S.J.
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yellowish colour gradually turned into red. The solution
was stirred at 08C for 10 h. Then, the mixture was treated
with water and extracted with CH Cl . The organic phase
2
2
(
was dried over anhyd. Na SO and filtered. The solvent
4
2
was removed in vacuo to get the product. FT-IR (KBr):
3
431, 2922, 2856, 1646, 1598, 1518, 1463, 1396, 1236,
(c) Tian, D.; Yan, H.; Li, H. Supramol. Chem. 2010, 22,
249–255. (d) Mart ´ı nez, R.; Espinosa, A.; T a´ rraga, A.;
Molina, P. Tetrahedron 2010, 66, 3662–3667.
(4) (a) Rodr ´ı guez-Morgade, M.; Planells, T.; Torres, T.;
2
107, 1033, 666 cm ; H NMR (CDCl , 500 MHz) d:
1 1
1
3
g,h
d
8
.01 (bm, H ), 7.90 (d, H , J ¼ 5 Hz), 7.72–7.48 (m,
e,f,b
o
a
p
H
), 7.12 (d, H , J ¼ 10 Hz), 7.07 (m, H ), 6.81 (d, H ,
n,q
r
Ballester, P.; Palomares, E. J. Mat. Chem. 2008, 18,
1
J ¼ 10 Hz,), 4.17 (d, H , J ¼ 10 Hz), 4.02–3.93 (m, H ),
76–181. (b) Choi, M.G.; Kim, Y.H.; Namgoong, J.E.;
j,m
k,l
.68–3.52 (m, H ), 3.15–3.09 (m, H ), 1.62 (s, ZCH ).
3
3
3
Chang, S.-K. Chem. Commun. 2009, 3560–3562.
(c) _Kim, J.H.; Kim, H.J.; Kim, S.H.; Lee, J.H.; Do, J.H.;
Kim, H.–J.; Lee, J.H.; Kim, J.S. Tetrahedron Lett. 2009, 50,
1
C NMR (CDCl , 125 MHz) d: 156.35, 152.25, 143.66,
3
1
1
1
4
34.37, 131.25, 129.80, 129.57, 128.01, 127.78, 126.22,
25.82, 125.70, 125.60 (unresolved), 123.75 (unresolved),
14.02, 111.40, 111.27, 111.18, 68.76, 66.85, 50.20,
4.79, 41.74, 31.02, 29.71, 29.44; anal. calcd for
5
958–5961. (d) Kwon, S.K.; Kim, H.N.; Rho, J.H.;
Swamy, K.M.K.; Shanthakumar, S.M.; Yoon, J. Bull. Korean
Chem. Soc. 2009, 30, 719–721. (e) Yang, Y.; Cao, X.;
Surowiec, M.; Bartsch, R.A. Tetrahedron 2010, 66,
447–452. (f) Guo, Z.-Q.; Chen, W.-Q.; Duan, X.-M.
Org. Lett. 2010, 12, 2202–2205. (g) Reynal, A.; Etxebarria,
J.; Nieto, N.; Serres, S.; Palomares, E.; Vidal-Ferran, A.
Eur. J. Inorg. Chem. 2010, 9, 1360–1365.
(
C H N O S ) : C, 72.46; H, 6.85; N, 4.29. Found: C,
59 67 3 6 2 n
7
2.35; H, 6.73; N, 4.20. GPC (using polystyrene standard
and THF eluent): M ¼ 2157, MWD 2.6.
w
(
5) (a) Lee, S.J.; Jung, J.H.; Seo, J.; Yoon, I.; Park, K.-M.;
Lindoy, L.F.; Lee, S.S. Org. Lett. 2006, 8, 1641–1643.
(b) Park, C.S.; Lee, J.Y.; Kang, E.-J.; Lee, J.-E.; Lee, S.S.
Tetrahedron Lett. 2009, 50, 671–674.
General procedure of fluorescence and UV–vis titrations
Stock solution of 1 was prepared in THF–water (8:2, v/v)
and 2 ml of the oligomer solution was taken in the cuvette.
Stock solutions of cations were prepared in water, and
were individually added in different amounts to the
(
6) Ghosh, S.; Dey, C.K.; Manna, R. Tetrahedron Lett. 2010, 51,
3177–3180.
7) Gore, P.H.; Wheeler, O.H. J. Am. Chem. Soc. 1961, 26, 3295.
(
(8) Rau, H. Angew. Chem. Int. Ed. Engl. 1973, 12, 224–235.