FLUORESCENT SENSORS BASED ON 2-SUBSTITUTED IMIDAZOLIDINES
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using the residual solvent signals as reference (CHCl3,
δ 7.25 ppm; DMSO-d5, δ 2.50 ppm). The IR spectra
were obtained on a Varian Excalibur 3100 FT-IR
instrument. The electronic absorption spectra were
measured on a Varian Cary-100 spectrophotometer.
The fluorescence spectra were recorded on a Hitachi
650-60 spectrofluorimeter. The melting points were
determined in glass capillaries using a PTP (M)
melting point apparatus. The progress of reactions and
the purity of products were monitored by TLC on
Silufol UV-254 plates using chloroform as eluent;
spots were visualized by treatment with iodine vapor in
a moist chamber.
spectrum, ν, cm–1: 1590, 1470, 1385. H NMR spec-
trum, δ, ppm: 2.63 m (2H, CH2N), 3.24 m (2H, CH2N),
3.42 d (2H, CH2C6H4, J = 14.7 Hz), 3.71 d (2H,
CH2C6H4, J = 13.7 Hz), 3.90 s (1H, CH), 6.50–7.65 m
(13H, Harom), 9.72 s (2H, OH). Fluorescence spectrum
(acetonitrile): λmax = 341 nm. Found, %: C 76.70;
H 6.67; N 7.84. C23H24N2O2. Calculated, %: C 76.64;
H 6.71; N 7.77.
1,3-Bis(2-hydroxybenzyl)-2-(naphthalen-1-yl)-
imidazolidine (VI) was synthesized from diamine II
and naphthalene-1-carbaldehyde. Yield 80%, mp 132–
133°C (from benzene). IR spectrum, ν, cm–1: 1595,
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1475, 1380, 1255. H NMR spectrum, δ, ppm: 2.68 m
Compounds III–VII (general procedure). A solu-
tion of 2 mmol of amine I or II in 10 ml of butan-1-ol
and 2 mmol of the corresponding aldehyde in the pres-
ence of acetic or p-toluenesulfonic acid as catalyst was
heated for 30–40 min. The solvent was removed under
reduced pressure, the residue was cooled, and the
precipitate was filtered off, washed with petroleum
ether, dried in air, and recrystallized from appropriate
solvent.
2-(Anthracen-9-yl)-1,3-dibenzylimidazolidine
(III) was synthesized from diamine I and anthracene-
9-carbaldehyde. Yield 83%, mp 177–178°C (from
butan-1-ol). IR spectrum, ν, cm–1: 1465, 1380. 1H NMR
spectrum, δ, ppm: 2.60 m (2H, CH2N), 3.26 d (2H,
CH2Ph, J = 13.6 Hz), 3.37 m (2H, CH2N), 3.64 d (2H,
CH2Ph, J = 12.7 Hz), 5.52 s (1H, CH), 6.95–7.63 m
(14H, Harom), 7.98 d (2H, 4′-H, 5′-H, J = 9.0 Hz),
8.42 s (1H, 10′-H), 8.70 br.s (1H, 1′-H), 9.84 br.s (1H,
(2H, CH2N), 3.35 m (2H, CH2N), 3.47 d (2H,
CH2C6H4, J = 14.1 Hz), 3.65 d (2H, CH2C6H4, J =
14.1 Hz), 4.50 s (1H, CH), 6.48–8.00 m (14H, Harom),
8.88 d (1H, Harom, J = 9.4 Hz), 9.48 s (2H, OH).
Fluorescence spectrum (acetonitrile): λmax = 341 nm.
Found, %: C 78.97; H 6.44; N 6.84. C27H26N2O2. Cal-
culated, %: C 79.00; H 6.38; N 6.82.
1,3-Bis(2-hydroxybenzyl)-2-(2-hydroxynaphtha-
len-1-yl)imidazolidine (VI) was synthesized from
diamine II and 2-hydroxynaphthalene-1-carbaldehyde.
Yield 84%, mp 147–148°C (from benzene). IR spec-
trum, ν, cm–1: 3330, 1600, 1475, 1380. 1H NMR spec-
trum, δ, ppm: 2.83 m (2H, CH2N), 3.48 m (2H, CH2N),
3.53 d (2H, CH2C6H4, J = 14.4 Hz), 3.72 d (2H,
CH2C6H4, J = 13.8 Hz), 4.74 s (1H, CH), 6.84–7.94 m
(14H, Harom), 9.12 s (1H, OH), 9.60 br.s (2H, OH).
Fluorescence spectrum (acetonitrile): λmax = 414 nm.
Found, %: C 75.95; H 6.23; N 6.65. C27H26N2O3. Cal-
culated, %: C 76.03; H 6.14; N 6.57.
8′-H). Fluorescence spectrum (acetonitrile): λmax
=
439 nm. Found, %: C 86.77; H 6.65; N 6.58. C31H28N2.
Calculated, %: C 86.88; H 6.59; N 6.53.
This study was performed under financial support
by the Russian Foundation for Basic Research (project
no. 09-03-00052), by the Ministry of Education and
Science of the Russian Federation (project
no. RNP.2.2.1.1.2348), and by the Council for Grants
at the President of the Russian Federation (project
no. NSh-363.2008.3).
2-(Anthracen-9-yl)-1,3-bis(2-hydroxybenzyl)-
imidazolidine (IV) was synthesized from diamine II
and anthracene-9-carbaldehyde. Yield 85%, mp 201–
202°C (from butan-1-ol). IR spectrum, ν, cm–1: 3385,
1
1595, 1480, 1387. H NMR spectrum, δ, ppm: 2.84 m
(2H, CH2N), 3.45 d (2H, CH2C6H4, J = 14.1 Hz),
3.55 m (2H, CH2N), 3.96 d (2H, CH2C6H4, J =
13.2 Hz), 5.48 s (1H, CH), 6.58–8.10 m (14H, Harom),
8.52 s (1H, 10′-H), 8.58 d (1H, 1′-H, J = 9.7 Hz),
9.07 d (1H, 8-H, J = 8.8 Hz), 9.17 s (1H, OH).
Fluorescence spectrum (acetonitrile): λmax = 417 nm.
Found, %: C 80.90; H 6.09; N 6.13. C31H28N2O2. Cal-
culated, %: C 80.84; H 6.13; N 6.08.
REFERENCES
1. de Silva, A.P., McClean, G.D., Moody, T.S., and
Weir, S.M., Handbook of Photochemistry and Photo-
biology, Nalwa, H.S., Ed., Stevenson Ranch, CA:
American Scientific, 2003, p. 217.
2. Bren’, V.A., Usp. Khim., 2001, vol. 70, p. 1152.
3. de Silva, A.P., Chem. Technol., 2009, vol. 6, no. 4, p. 25.
4. Shihadeh, Y.A., Benito, A., Lloris, J.M., Martínez-
Máñez, R., Pardo, T., Soto, J., and Marcos, M.D.,
J. Chem. Soc., Dalton Trans., 2000, p. 1199.
1,3-Bis(2-hydroxybenzyl)-2-phenylimidazolidine
(V) was synthesized from diamine II and benzalde-
hyde. Yield 73%, mp 182–183°C (from benzene). IR
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 8 2010