NJC
Paper
has not been confirmed unequivocally but it has been suggested
by others to occur via extrusion of the acetate group and
6 F. Arnaud-Neu, E. M. Collins, M. Deasy, G. Ferguson, S. J. Harris,
B. Kaitner, A. J. Lough, M. A. McKervey, E. Marques, B. L. Ruhl,
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7 R. Joseph and C. P. Rao, Chem. Rev., 2011, 111, 4658–4702.
8 P. E. Georghiou, S. Rahman, G. Valluru, L. N. Dawe,
S. M. S. Rahman, A. N. Alodhayb and L. Y. Beaulieu,
New J. Chem., 2013, 37, 1298–1301.
1
5
direct sulphur–Au bond formation. Regardless, the strong MCL
2
+
response to aqueous Ca in 1 was not seen with 3 which,
+
instead, showed sensitivity to aqueous Cs and to a lesser-
+
+
extent to Rb ions and a negligible response to K . This selectivity
suggests that a suite of similar bimodally-functionalized calix-
arenes can be tailor-made to respond to a mixture of metal
cations with a multi-MCL device in which several MCLs with
suitable reference MCLs can be developed, a goal which we are
striving to achieve.
9 A. Alodhayb, S. M. Saydur Rahman, S. Rahman,
G. K. Valluru, P. E. Georghiou and L. Y. Beaulieu, Sens.
Actuators, B, 2014, 203, 766–773.
1
0 For an earlier report on using thioacetate-functionalized
calix[4]arenes for SAM formation on Au, Pt and Pd, see
G. Genorio, T. He, A. Meden, S. Polanc, J. Jamnik and
J. M. Tour, Langmuir, 2008, 24, 11523–11532.
Acknowledgements
We thank the research support from the Research Development
Corporation, Vale, Memorial University of Newfoundland and
the Ministry of Higher Education, Kingdom of Saudi Arabia for
the scholarship to AA. Dr Bo Li, Boston College X-ray facility
is acknowledged for the single crystal X-ray data collection.
Dr S. M. Saydur Rahman is thanked for help with the SPIP and
helpful discussions.
1
1
1
1
1 B. Chailap and T. Tuntulani, Org. Biomol. Chem., 2012, 10,
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2 K. Y. Manning, N. R. Butt, A. Alodhayb, I. Saika-Voivod and
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3 M. Kimura, M. Yokokawa, S. Sato, T. Fukawa and T. Mihara,
Chem. Lett., 2011, 40, 1402–1404.
4 Crystal data for
3 (acetonitrile : ethanol): C H O S
62 88 9
2
ꢁ
1
(M = 1041.44 g mol ): monoclinic, space group P2
1
/n
(
no. 14), a = 21.9907(9) Å, b = 27.7429(14) Å, c = 29.1299(12) Å,
Notes and references
3
b = 95.471(3), V = 17 690.8(14) Å , Z = 12, T = 296.15 K,
m(CuKa) = 1.242 mm , Dcalc = 1.173 g cm , 236792 reflec-
tions measured (4.82 r 2Y r 95.672), 16 373 unique (Rint
0.1965, Rsigma = 0.1372) which were used in all calculations.
The final R was 0.1519 (I 4 2s(I)) and wR was 0.4584 (all
ꢁ
1
ꢁ3
1
For reviews on calixarenes, see (a) C. D. Gutsche, Calixarenes:
An Introduction, Royal Society of Chemistry, Cambridge, UK,
=
2nd edn, 2008; (b) in Calixarenes 2001, ed. Z. Asfari,
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1
2
Publishers, Dordrecht, The Netherlands, 2001; (c) Calixarenes
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2
3
(c) C. J. Evans and G. P. Nicholson, Sens. Actuators, B, 2005,
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2
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4
5
F. Arnaud-Neu, S. Fanni, L. Guerra, W. M. McGregor, K. Ziat, 17 G. W. Gokel, in Encyclopedia of Supramolecular Chemistry,
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and will be reported in due course.
5
872 | New J. Chem., 2014, 38, 5868--5872
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