Substituted 1,5-diphenyl-3-benzothiazol-2-yl-Δ2-pyrazolines: synthesis, X-ray structure, photophysics, and cation complexation properties

Journal of Physical Chemistry A

Volumn 104, Issue 26, 2000, Pages 6171-6188

  Rurack, Knut ^a,b   Bricks, Julia L ^c   Schulz, Burkhard ^b   Maus, Michael ^d   Reck, Günter ^b   Resch Genger, Ute ^b  

^a HUMBOLDT UNIVERSITY   (Germany)

^b BAM FEDERAL INSTITUTE FOR MATERIALS RESEARCH AND TESTING   (Germany)

^c INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

^d UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; CROWN ETHERS; ELECTROCHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC SOLVENTS; PHOTOCHEMICAL REACTIONS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

FLUORESCENCE SPECTROSCOPY; INTRAMOLECULAR ELECTRON TRANSFER; PHOTOPHYSICS;

CHROMOPHORES;

EID: 0034229880     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp993404q     Document Type: Article

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102. g were obtained from the optimized geometry in the ground state by semiempincal calculations (AM1).
103. 108 resulting in a modified Lippert-Mataga eq 15. (equation presented)
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117. 17a,49
118. Moreover, for 1a and 1b in ethanol, no phosphorescence at 77 K could be detected in the spectral region of 430-900 nm and at various delay times in the range of 0.05-100 ms employing the Perkin-Elmer LS50B spectrometer with low-temperature luminescence accessory, flash lamp excitation (fwhm < 10 μs), and gated PMT (the same is found for the reference compound 2a between 370 and 900 nm). These results were confirmed by measurements of fluorescence polarization in ethanol at 77 K (Spectronics Instruments 8100 fluorometer. He cryostat) according to the method of photoselection (Albrecht, A. C. J. Mol. Spectrosc. 1961, 6, 84) which allows to discriminate between (overlapping) transitions of different nature (see, e.g., Gudipati, M. S.; Maus, M.; Daverkausen, J.; Hohlneicher, G. Chem. Phys. 1995, 192, 37). For all four compounds, the degree of anisotropy is constant (±0.05) over the whole range of the emission spectrum (440-650 nm, 1a and 1b; 380-560 nm, 2a).
119. Moreover, for 1a and 1b in ethanol, no phosphorescence at 77 K could be detected in the spectral region of 430-900 nm and at various delay times in the range of 0.05-100 ms employing the Perkin-Elmer LS50B spectrometer with low-temperature luminescence accessory, flash lamp excitation (fwhm < 10 μs), and gated PMT (the same is found for the reference compound 2a between 370 and 900 nm). These results were confirmed by measurements of fluorescence polarization in ethanol at 77 K (Spectronics Instruments 8100 fluorometer. He cryostat) according to the method of photoselection (Albrecht, A. C. J. Mol. Spectrosc. 1961, 6, 84) which allows to discriminate between (overlapping) transitions of different nature (see, e.g., Gudipati, M. S.; Maus, M.; Daverkausen, J.; Hohlneicher, G. Chem. Phys. 1995, 192, 37). For all four compounds, the degree of anisotropy is constant (±0.05) over the whole range of the emission spectrum (440-650 nm, 1a and 1b; 380-560 nm, 2a).
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141. Note that these are the lifetimes of the complex(es) after 1 day of equilibration.
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144. 50
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148. (equation presented) (ref 56). For a definition of parameters, see section 3.1.2.
149. Notario, R.; Herreros, M.; Ballesteros, E.; Essefar, M.; Abboud, J.-L. M.; Sadekov, I. D.; Minkin, V. I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1994, 2341.
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152. II complexation with 2-thien-2-yl-pyridine (log K = 0.2. Sigel, H.; Wynberg, H.; van Bergen, T. J.; Kahmann, K. Helv. Chim. Acta 1972, 55, 610) and 4-pyrid-2-yl-imidazole (log K = 8.76. Eilbeck, W. J.; Holmes, F.; Phillips, G. C.; Underhill, A. E. J. Chem. Soc. A 1967, 1161).
153. II complexation with 2-thien-2-yl-pyridine (log K = 0.2. Sigel, H.; Wynberg, H.; van Bergen, T. J.; Kahmann, K. Helv. Chim. Acta 1972, 55, 610) and 4-pyrid-2-yl-imidazole (log K = 8.76. Eilbeck, W. J.; Holmes, F.; Phillips, G. C.; Underhill, A. E. J. Chem. Soc. A 1967, 1161).
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157. III in acidic solution yielding an intense blue colour.
158. 53 was also detected during our studies.
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163. 2-pyrazolines has to be taken into account (Yamamoto, H.; Sano, Y.; Shirota, Y.; Seki, H.; Mikawa, H. Bull. Chem. Soc. Jpn. 1979, 52, 1533. Grimshaw, J.; de Silva, A. P. J. Chem. Soc., Perkin Trans. 2 1983, 1679). Here, only for 1c the occurrence of such a photoreaction could be verified when using comparatively high laser power (>9 kW pulse peak power) for excitation of a sample.
164. 2-pyrazolines has to be taken into account (Yamamoto, H.; Sano, Y.; Shirota, Y.; Seki, H.; Mikawa, H. Bull. Chem. Soc. Jpn. 1979, 52, 1533. Grimshaw, J.; de Silva, A. P. J. Chem. Soc., Perkin Trans. 2 1983, 1679). Here, only for 1c the occurrence of such a photoreaction could be verified when using comparatively high laser power (>9 kW pulse peak power) for excitation of a sample.
165. de Silva, A. P.; Gunaratne, H. Q. N.; Kane, A. T. M.; Maguire, G. E. M. Chem. Lett. 1995, 125. de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Nieuwenhuizen, M. Chem. Commun. (Cambridge) 1996, 1967.
166. de Silva, A. P.; Gunaratne, H. Q. N.; Kane, A. T. M.; Maguire, G. E. M. Chem. Lett. 1995, 125. de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Nieuwenhuizen, M. Chem. Commun. (Cambridge) 1996, 1967.
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168. Huston, M. E.; Haider, K. W.; Czarnik, A. W. J. Am. Chem. Soc. 1988, 110, 4460. de Silva, A. P.; Gunaratne, H. Q. N. J. Chem. Soc., Chem. Commun. 1990, 186.
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170. Siebrand, W. J. Chem. Phys. 1967, 46, 440. Siebrand, W. J. Chem. Phys. 1967, 47, 2441.
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180. rel〉 = 0.82) and 0.34 ns.
181. Atomic deviations from the planes (Å). 1b: plane 1 = 0.043 N(1), -0.003 N(2), -0.037 C(3), 0.055 C(4), -0.057 C(5); plane 2 = 0.002 C(6), -0.003 C(7), 0.002 C(8), 0.002 C(9), -0.003 C(10), 0.001 C(11); plane 3 = -0.002 C(12), -0.011 N(13), 0.018 S(14), -0.005 C(15), -0.003 C(16), 0.008 C(26), 0.012 C(27), -0.005 C(28). -0.012 C(29); plane 4 = 0.001 C(18), -0.001 C(19), 0.000 C(20), 0.001 C(21), -0.001 C(22), 0.000 C(23). 2a: plane 1 = 0.063 N(1), -0.024 N(2), -0.026 C(3), 0.057 C(4), -0.070 C(5); plane 2 = 0.012 C(6), -0.012 C(7), -0.002 C(8), 0.015 C(9), -0.014 C(10), 0.001 C(11); plane 3 = -0.001 C(12), 0.003 C(13), -0.002 C(H), 0.000 C(15), 0.002 C(16), -0.002 C(17); plane 4 = -0.017 C(18), 0.013 C(19), 0.002 C(20), -0.013 C(21), 0.009 C(22), 0.006 C(23). 3: plane 1 = 0.057 N(1), -0.011 N(2), -0.041 C(3), 0.066 C(4), -0.072 C(5); plane 2 = -0.009 C(6), 0.003 C(7), 0.003 C(8), -0.002 C(9), -0.003 C(10), 0.009 C(11); plane 3 = 0.015 C(12), -0.009 N(13), 0.011 S(14), -0.014 C(15), -0.006 C(16), -0.007 C(26), 0.017 C(27), 0.017 C(28), -0.025 C(29); plane 4 = 0.003 C(18), -0.001 C(19), 0.004 C(20), -0.009 C(21), 0.010 C(22), -0.007 C(23).
182. i
183. 83
184. II as well. However, the occurrence of these trace metal ions at such concentrations is barely found in matrices where fluorescence sensing is commonly employed.
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