A New Fluoride Selective Fluorescent as Well as Chromogenic

Eun Jin Cho,† Jung Wha Moon,† Seung Whan Ko,† Jin Yong Lee,*,† Sook Kyung Kim,‡. Juyoung Yoon,‡ and Kye Chun Nam*,†. Department of Chemi...
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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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