Fluorescent Probes
FULL PAPER
standard for compounds 1–3. The quantum yield was calculated using the
following Equation (1):
[4] For selective examples, see: a) W. Lin, C. Albanese, R. G. Pestell,
[5] a) Y. Zhao, Q. Zheng, K. Dakin, K. Xu, M. L. Martinez, W.-H. Li, J.
2
Ff ¼ FrðArFs=AsFrÞðhs2=hr
Þ
ð1Þ
where, As and Ar denote the absorbance of the sample and the reference,
respectively, at the same excitation wavelength, Fs and Fr are the corre-
sponding relative integrated fluorescence intensities, and h is the refrac-
tive index of the solvent.
2-(4-(1,3-Dithian-2-yl)phenyl)-1H-phenanthro
ACHTUNGTNER[NUNG 9,10-d]imidazole (1): Com-
b) P. C. Bulmann Page, M. B. V. Niel, J. C. Prodger, Tetrahedron
1989, 45, 7643–7677; c) A. T. Khan, E. Mondal, P. R. Sahu, S. Islam,
Tetrahedron Lett. 2002, 43, 919–922; d) H. M. Meshram, G. S.
b) A. V. Rama Rao, G. Venkatswamy, S. M. Javeed, V. H. Desh-
15–18; b) E. Fujita, Y. Nagao, K. Kaneko, Chem. Pharm. Bull. 1978,
1988, pp. 109–113; c) T. Nakatsuka, H. Iwata, R. Tanaka, S. Lmajo,
[13] a) M. S. Tsai, Y. C. Hsu, J. T. Lin, H. C. Chen, C. P. Hsu, J. Phys.
[14] A. R. Day, E. A. Steck, J. Am. Chem. Soc. 1943, 65, 452–456.
[15] a) I. B. Berlman, Handbook of fluorescence spectra of aromatic mol-
ecules, Academic Press, New York, 1971; b) A. Ajayaghosh, P.
[17] For selective examples of ratiometric probes and books, see: a) J. R.
Lakowicz, Topics in Fluorescence Spectroscopy, Vol. 4, Probe Design
and Chemical Sensing, Kluwer Academic, New York, 2002, pp. 1–
105; b) H. Takakusa, K. Kikuchi, Y. Urano, H. Kojima, T. Nagano,
pound (100.00 mg, 0.31 mmol) and 1,3-propanedithiol (0.03 mL,
2
3.10 mmol) were dissolved in DMF (1 mL) at room temperature under
the nitrogen atmosphere, and Et2O·BF3 (10 mL) was then added. After
48 h at room temperature, the solvent was removed under reduced pres-
sure and the residue was then purified by chromatography on silica gel
(CH2Cl2/petroleum ether 1:4) to give
1 as a white solid (92.8 mg,
0.25 mmol, 75%). M.p. 224–2268C; 1H NMR (400 MHz, [D6]DMSO,
258C, TMS): d=1.76–1.82 (m, 1H), 2.16–2.20 (m, 1H), 2.96 (t, 2H), 3.15
(t, 2H), 5.52 (s, 1H), 7.64–7.69 (m, 4H), 7.72–7.79 (m, 2H), 8.30 (d, J=
8.8 Hz, 2H), 8.55 (d, J=8.0 Hz,1H), 8.60 (d, J=8.4 Hz, 1H), 8.85 (d, J=
8.8 Hz,1H), 8.89 ppm (d, J=8.4 Hz,1H); MS (ESI): m/z (%): 413.1 (80)
[M+H+]; elemental analysis calcd (%) for C21H20N2O3: C 72.78, H 4.89,
N 6.79; found: C 72.57, H 4.62, N 7.08.
Spectral measurements: Metal chlorate (Fe2+, Hg2+, Ni2+, Ca2+, Mg2+
,
Cd2+, Cu2+, Co2+, Zn2+, Na+, K+, Al3+), nitrate (Ag+) or sulfate (Mn2+
) stock solutions were used. Probe 1 was dissolved in acetonitrile at room
temperature to afford the probe stock solution (50 mm). Test solutions
were prepared by placing 0.5 mL of the probe stock solution and an ap-
propriate aliquot of each metal stock into a 5 mL volumetric flask, and
diluting the solution to 5 mL with acetonitrile. The resulting solution was
shaken well before recording the absorption and emission spectra. Unless
otherwise noted, for all measurements, the excitation wavelength was
362 nm, and both the excitation and emission slit widths were 2.5 nm.
Acknowledgements
Funding was partially provided by the Key Project of Chinese Ministry
of Education (108167), the National Science Foundation of China
(20872032), the Scientific Research Foundation for the Returned Over-
seas Chinese Scholars, State Education Ministry (2007-24), and the
Hunan University research funds.
[1] For review and books, see: a) P. G. M. Wuts, T. W. Greene, Greeneꢀs
Protective Groups in Organic Synthesis, 4th ed., Wiley, New York,
2007; b) G. Sartori, R. Ballini, F. Bigi, G. Bosica, R. Maggi, P. Righi,
[3] a) A. Paola, P. J. Wirz, Photochem. Photobiol. Sci. 2002, 1, 441–458;
b) M. Goeldner, R. Givens, Dynamic Studies In Biology, Phototrig-
gers, Photoswitches and Caged Biomolecules, Wiley-VCH, Wein-
heim, 2005; c) G. Marriot, Methods Enzymol. 1998, 291, 1–529.
Received: July 24, 2008
Revised: October 17, 2008
Published online: December 3, 2008
Chem. Eur. J. 2009, 15, 1030 – 1035
ꢀ 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
1035