A new fluoride selective fluorescent as well as chromogenic chemosensor containing naphthalene urea derivative Eun Jin Cho, Jung Wha Moon, Seung Whan Ko, Jin Yong Lee*, Sook Kyung Kim,† Juyoung Yoon† and Kye Chun Nam* Department of Chemistry and Institute of Basic Science, Chonnam National University, Kwangju 500-757, Korea, Department of Chemistry, Ewha Womans University,11-1 Daehyun-dong, Seodaemun-gu, Seoul 120-750, Korea E-mail:
[email protected] Supporting Information
Contents 1. Fluorescent titrations of compound 1 (6 µM) with tetrabutylammonium fluoride in acetonitrile-DMSO (9:1, v/v) (excitation wavelength = 310 nm). (Figure S1) 2. UV-vis spectra of solutions containing 1 and F- in acetonitrile-DMSO. (Figure S2) 3. Calculated energies of 1, 1-, and (1F-). (Table S1) 4. The AM1 predicted structures of 1 and 1F-. (Figure S3)
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400 Comp 1 only. 1 + F- 1eq. 1 + F- 10eq. 1 + F- 50eq.
Intensity
300
200
100
0 350
400
450
500
550
600
Wavelength(nm)
Figure S1. Fluorescent titrations of compound 1 (6 µM) with tetrabutylammonium fluoride in acetonitrile-DMSO (9:1, v/v) (excitation wavelength = 310 nm).
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[F-] / [naphthalene] = 50 [F-] / [naphthalene] = 5 [F-] / [naphthalene] = 2 [F-] / [naphthalene] = 1 [F-] / [naphthalene] = 0.5 naphthalene alone
Figure S2. UV-vis spectra of solutions containing 1 (300 µM) and fluoride ion acetonitrile-DMSO (1:1, v/v).
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Table S1. Calculated energies of 1, 1-, and (1F-). 1 11 -’ Energya 0.0944347 0.0272399 0.0357963
1F-0.1015643
1F-’ -0.0939494
ADE (∆E)b Erelc
-126.43 -4.78
-121.65
1.83 -5.37
1.60
a
Energies are in Hartree. bAdiabatic electron detachment energies (ADEs) for 1- and 1-’
are in eV, and binding energies (∆Es) for 1F- and 1F-’ are in kcal/mol. cErel represents the relative energies (in kcal/mol) of 1- and 1F- with respect to 1-’ and 1F-’, respectively.
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Figure S3. The AM1 predicted structures of 1 and 1F-.
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