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It has been reported (see: Sessler, J. L, Cho, W.-S, Gross, D. E, Shriver, J. A, Lynch, V. M, Marquez, M. J. Org. Chem. 2005, 70, 5982-5986) that the yield of fluorinated calix[n]pyrroles can be increased by addition of tetrabutylammonium chloride (TBACl) to the reaction mixtures during their synthesis. It is expected that the chloride anion acts as a template for the formation of the calix[n]pyrrole ring system. However, addition of TBACl to a mixture of 1, 2, and a catalytic amount of Et 2O·F3 did not result in an increased yield, and the receptor 3 was obtained in 16% yield. This observation is most likely because of the fact that two of the pyrrole units in the calix[4]pyrrole ring system have been substituted by two thiophene moieties that are not capable of forming hydrogen bonds to the templating chloride anion see ref 18a, Binding studies between the receptor 3 and TBACl carried out in a CDCI 3
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1H NMR spectra (see Supporting Information) recorded of 3 and a mixture of 3 and TBACl were essentially identical, indicating that no binding between the receptor 3 and the chloride anion takes place in solution.
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.+) which normally appears at g values around 2.009 see: Wudl, F.; Smith, G. M.; Hufnagel, E. J. J. Chem. Soc., Chem. Commun. 1970, 1453-1454
-
.+) which normally appears at g values around 2.009 (see: Wudl, F.; Smith, G. M.; Hufnagel, E. J. J. Chem. Soc., Chem. Commun. 1970, 1453-1454
-
-
-
-
57
-
-
0013454324
-
-
.-) which normally appears at g values around 2.003
-
.-) which normally appears at g values around 2.003
-
-
-
-
58
-
-
0000626922
-
-
see
-
(see: Bryce, M. R.; Moore, A. J.; Tanner, B. K.; Whitehead, R.; Clegg, W.; Gerson, F.; Lamprecht, A.; Pfenninger, S. Chem. Mater. 1996, 8, 1182-1188).
-
(1996)
Chem. Mater
, vol.8
, pp. 1182-1188
-
-
Bryce, M.R.1
Moore, A.J.2
Tanner, B.K.3
Whitehead, R.4
Clegg, W.5
Gerson, F.6
Lamprecht, A.7
Pfenninger, S.8
-
59
-
-
38549165372
-
-
2Ch to determine the stoichiometry between 3 and TCNQ in solution; however, no reliable results were obtained.
-
2Ch to determine the stoichiometry between 3 and TCNQ in solution; however, no reliable results were obtained.
-
-
-
-
60
-
-
21544435239
-
-
Chappell, J. S.; Bloch, A. N.; Bryden, W. A.; Maxfield, M. O.; Poehler, T.; Cowan, D. O. J. Am. Chem. Soc. 1981, 103, 2442-2443.
-
(1981)
J. Am. Chem. Soc
, vol.103
, pp. 2442-2443
-
-
Chappell, J.S.1
Bloch, A.N.2
Bryden, W.A.3
Maxfield, M.O.4
Poehler, T.5
Cowan, D.O.6
-
61
-
-
0001366703
-
-
Flandrois, S.; Chasseau, D. Acta Crystallogr., Sect. B 1977, 33, 2744-2750.
-
(1977)
Acta Crystallogr., Sect. B
, vol.33
, pp. 2744-2750
-
-
Flandrois, S.1
Chasseau, D.2
-
62
-
-
0001054627
-
-
Long, R. E.; Sparks, R. A.; Trueblood, K. N. Acta Crystallogr. 1965, 18, 932-939.
-
(1965)
Acta Crystallogr
, vol.18
, pp. 932-939
-
-
Long, R.E.1
Sparks, R.A.2
Trueblood, K.N.3
-
63
-
-
0001879385
-
-
Hoekstra, A.; Spoelder, T.; Vos, A. Acta Crystallogr., Sect. B 1972, 28, 14-25.
-
(1972)
Acta Crystallogr., Sect. B
, vol.28
, pp. 14-25
-
-
Hoekstra, A.1
Spoelder, T.2
Vos, A.3
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