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4
5
.
.
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Martinez-Manez R, Sancenón F (2003) Fluorogenic and chromo-
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with increasing concentration of selected ions were per-
formed. As shown in the Fig. 8, fluorescence intensity of
NAC4 gradually decrease upon increasing the concentration
4
419–4476
Liang Z, Liu Z, Jiang L, Gao Y (2007) A new fluorescent
chemosensor for copper (II) and molecular switch controlled by
light. Tetrahedron Lett 48(9):1629–1632
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switch on–off–on receptor constructed of quinoline allied calix [4]
arene for selective recognition of Cu 2+ from blood serum and F−
from industrial waste water. Analyst 138(9):2531–2535
2
+
−
−5
of Cu and I Detection limit was calculated 1.05×10 and
.
5
4
.0×10− M.
1
HNMR Study
6
.
Valeur B, Leray I (2000) Design principles of fluorescent molecular
sensors for cation recognition. Coord Chem Rev 205(1):3–40
1
HNMR spectra of complexes were also recorded to explore
the binding mechanism of ions with ligand. The spectra were
recorded in DMSO-d at 25 °C. Figure 11 displays the chem-
ical shifts of NAC4 upon the addition of Cu and I . In the
NAC4-Cu complex there is charge transfer from ligand to
metal through carbonyl oxygen and nitrogen electron pairs
since there is no change in amide protons. While in NAC4-
I the amide protons at 8.0 changes to a broad peak and also
9
7. Duke RM, Veale EB, Pfeffer FM, Kruger PE, Gunnlaugsson T
(2010) Colorimetric and fluorescent anion sensors: an overview
of recent developments in the use of 1, 8-naphthalimide-based
chemosensors. Chem Soc Rev 39(10):3936–3953
6
2
+
−
2
+
8
.
Gunnlaugsson T, Glynn M, Tocci GM, Kruger PE, Pfeffer FM
2006) Anion recognition and sensing in organic and aqueous me-
(
dia using luminescent and colorimetric sensors. Coord Chem Rev
250(23):3094–3117
Kim JS, Quang DT (2007) Calixarene-derived fluorescent probes.
Chem Rev 107(9):3780–3799
−
9
.
.0 and 9.23 ppm are merged to single broad peak at 9.25 ppm
indicating N-H deprotonation promoted by (i) the intrinsic
acidity of NAC4 enhanced by conjugation of nitrogen lone-
pair electrons with the aromatic ring and (ii) the high stability
of the [HI] hydrogen-bonding complex. Moreover, some
changes also occurred in aromatic protons of naphthalene with
brooding of peaks [27].
1
0. Kurzątkowska K, Sayin S, Yilmaz M, Radecka H, Radecki J (2015)
Calix [4] arene derivatives as dopamine hosts in electrochemical
sensors. Sensor Actuat B-Chem 218:111–121
−
11. Karakuş ÖÖ, Deligöz H (2008) Azocalixarenes. 8: synthesis and
investigation of the absorption spectra of di-substituted azocalix [4]
arenes containing chromogenic groups. J Incl Phenom Macro 61(3–
4):289–296
1
2. Gutsche CD, Lin L-G (1986) Calixarenes 12: the synthesis of func-
tionalized calixarenes. Tetrahedron 42(6):1633–1640
1
3. Sahin O, Yilmaz M (2012) Synthesis and fluorescence sensing
properties of a new naphthalimide derivative of calix [4] arene.
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Conclusions
1
4. Othman AB, Lee JW, Wu J-S, Kim JS, Abidi R, Thuéry P, Strub
JM, Van Dorsselaer A, Vicens J (2007) Calix [4] arene-based,
Hg2 + −induced intramolecular fluorescence resonance energy
transfer chemosensor. The J Org Chem 72(20):7634–7640
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and ratiometric probes. Inorg Chem 44(6):2018–2030
In summary, we have successfully developed naphthalene
2
+
−
appended calix[4]arene based Cu and I florescence sensor.
The binding properties of ions were fully investigated though
different methods. It showed high selectivity and sensitivity
and low detection limit. The nature of the ion receptor inter-
1
1
action has been defined by absorption and HNMR spectros-
copy that proved that synthesized NAC4 is photophysical rich
structure and very promising,
16. Leray I, Lefevre JP, Delouis JF, Delaire J, Valeur B (2001)
Synthesis and photophysical and cation-binding properties of
mono-and Tetranaphthylcalix [4] arenes as highly sensitive and
selective fluorescent sensors for sodium. Chem-A Eur J 7(21):
4
590–4598
1
1
1
2
7. Choi JK, Kim SH, Yoon J, Lee K-H, Bartsch RA, Kim JS (2006) A
PCT-based, pyrene-armed calix [4] crown fluoroionophore. J Org
Chem 71(21):8011–8015
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triphenylamine units. Spectrochim Acta A 114:190–196
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arene based highly efficient fluorescent sensor for Au3+ and I−. J
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bisimide-armed calix [4]-aza-crown as Bturn on^ fluorescent sensor
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Acknowledgments We thank the Scientific and Technological
Research Council of Turkey (TUBITAK acceptance letter number:
5
3325897-216.01-153062), Selcuk University, Konya and National
Center of Excellence in Analytical Chemistry, University of Sindh,
Jamshoro/Pakistan for the financial support of this work.
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