3
4
J Incl Phenom Macrocycl Chem (2011) 70:29–35
naked eye depending on the concentration of the solution.
The solution of receptor 2 showed more intense color
change than the receptor 1 for the most of the anions
investigated. In addition, despite of simpler structures than
the receptors 3 and 4 with a benzophenone group as a
chromogenic signaling subunit [34, 35], the receptors 1 and
11. Bhosale, S.V., Bhosale, S.V., Kalyankar, M.B., Langford, S.: A
core-substituted naphthalene diimide fluoride sensor. J. Org. Lett.
1
1, 5418–5421 (2009)
1
1
2. Lin, Y.-C., Chen, C.-T.: Acridinium salt-based fluoride and
acetate chromofluorescent probes: molecular insights into anion
selectivity switching. Org. Lett. 11, 4858–4861 (2009)
3. Jose, D.A., Kumar, D.K., Ganguly, B., Das, A.: Efficient and
simple colorimetric fluoride ion sensor based on receptors having
urea and thiourea binding sites. Org. Lett. 6, 3445–3448 (2004)
2
showed more intense color change at the same concen-
tration of host and anions. This result suggests that the
benzophenone moiety may not act as a chromogenic sig-
naling subunit, unlikely we have proposed in the previous
study [34, 35]. In this case, single nitrophenyl group is
better than dual chromophore.
14. Hayashita, T.; Onodera, T.; Kato, R.; Nishizawa, S.; Teramae, N.:
Positioning dependent anion recognition by thiourea-based
chromoionophores via hydrogen bonding in aqueous vesicle
solutions. Chem. Commun. 755–756 (2000)
1
5. Kato, R., Nishizawa, S., Hayashita, T., Teramae, N.: A thiourea-
based chromoionophore for selective binding and sensing of
acetate. Tetrahedron Lett. 42, 5053–5056 (2001)
The changes of solution color on additions of anion were
shown in Fig. 7 with structures of hosts.
1
6. Lee, D. H.; Lee, H. Y.; Lee, K. H.; Hong, J.-I. : Selective anion
sensing based on a dual-chromophore approach. Chem. Commun.
In summary, we developed new chromogenic anion
receptors 1 and 2 with a nitrophenyl group as a signaling
group. The receptor 1 formed the hydrogen-bonded com-
plex with various anions except fluoride. However, the
receptor 2 formed deprotonated receptor immediately with
various anions. Therefore, they operated based on a
hydrogen bonding and an acid–base equilibrium. In addi-
tion, the receptors 1 and 2 proved to be efficient naked-eye
detectors despite of their simple structures.
1
188–1189 (2001)
17. Tozawa, T., Misawa, Y., Tokita, S., Kubo, Y.: A regioselectively
bis(thiourea)-substituted dibenzo-diaza-30-crown-10: a new strat-
egy for the development of multi-site receptors. Tetrahedron Lett.
4
1, 5219–5223 (2000)
1
1
8. Gunnlaugsson, T.; Davis, A. P.; Glynn, M.: Fluorescent photo-
induced electron transfer (PET) sensing of anions using charge
neutral chemosensors. Chem. Commun. 2556–2557 (2001)
9. Sasaki, S., Citterio, D., Ozawa, S., Suzuki, K.: Design and syn-
thesis of preorganized tripodal fluororeceptors based on hydrogen
bonding of thiourea groups for optical phosphate ion sensing.
J. Chem. Soc. Perkin Trans. 2, 2309–2313 (2001)
Acknowledgements Financial support from Korea Ministry Envi-
ronment ‘‘ET-Human resource development Project’’ and the Korean
Science & Engineering Foundation (R01-2008-000-20704-0 and
20. Hennrich, G., Sonnenschein, H., Resch-Genger, U.: Fluorescent
anion receptors with iminoylthiourea binding sites—selective
2
-
-
hydrogen bond mediated recognition of CO , HCO3 and
3
2-
2
009-0074066) is gratefully acknowledged.
HPO4 . Tetrahedron Lett. 42, 2805–2808 (2001)
2
2
1. Mei, M.H., Wu, S.K.: A study on anion recognition by a naph-
thyl-thiourea derivative. Acta Chim. Sin. 59, 1112–1115 (2001)
2. Jim e´ nez, D., Mart ´ı nez-M a´ n˜ ez, R., Sancen o´ n, F., Soto, J.: Selec-
tive fluoride sensing using colorimetric reagents containing
anthraquinone and urea or thiourea binding sites. Tetrahedron
Lett. 43, 2823–2825 (2002)
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