K. Maurer, K. Hager, A. Hirsch
FULL PAPER
2
H, CH2, CH3), 3.90 (m, 8 H, CH2N), 5.00 (d, JH,H = 12.1 Hz, 4
8.0 Hz, 8 H, Py) 8.21 (s, 8 H, Bn), 8.24, (br., 8 H, Bn), 8.65 (br., 8
H, Bn), 8.81 (s, 4 H, Bn), 8.87 (br., 8 H, pyrrole β-H), 9.48 (br., 8
H, CONH), 10.02 (br., 8 H, CONH) ppm. UV/Vis (CHCl3): λmax
(ε) = 302 (53000), 422 (117000), 518 (6000), 552 (3000), 592 (2000),
648 (2000) nm.
H, Bn-CH2), 5.07 (d, 2JH,H = 12.1 Hz, 4 H, Bn-CH2), 5.14 (d, 2JH,H
2
= 12.0 Hz, 4 H, Bn-CH2), 5.20 (d, JH,H = 12.1 Hz, 4 H, Bn-CH2),
3
3
5.80 (d, JH,H = 2.81 Hz, 4 H, CH*), 5.89 (d, JH,H = 2.81 Hz, 4
H, CH*), 7.07–7.39 (m, 48 H, Bn, Bz), 7.49 (m, 4 H, Bz), 7.85 (t,
3JH,H = 8.1 Hz, 8 H, Py), 7.87 (d, JH,H = 8.1 Hz, 8 H, Bz), 8.02
3
Complexation of
1 with 11: Dendron 11 (4 equiv., 7.42 mg,
3
3
(d, JH,H = 8.1 Hz, 8 H, Py), 8.14 (d, JH,H = 8.2 Hz, 8 H, Py),
8.21 (s, 8 H, Bn) 8.37 (br., 8 H, Bn), 8.54 (br., 8 H, Bn), 8. 61 (s, 4
H, Bn-CH), 8.87 (br., 8 H, pyrrole β-H), 9.51 (br., 8 H, CONH),
10.03 (br., 8 H, CONH) ppm. UV/Vis (CHCl3): λmax (ε) = 302
(98000), 421.5 (142000), 518.5 (7000), 552.5 (4000), 591.5 (2000),
647.5 (2000) nm.
22.52·10–4 mmol) was added to compound
1
(1.54 mg,
5.63·10–4 mmol), suspended in CHCl3 (5 mL, HPLC grade). The
1
solution was stirred at room temp. for 13 h. H NMR (400 MHz,
CDCl3, 25 °C): δ = –2.82 (br., 2 H, pyrrole NH), 0.83–2.45 (m, 280
H, CH2, CH3), 3.18 (m, 56 H, CH2N), 3.84 (br., 16 H, CONH),
5.18 (m, 64 H, Bn-CH2), 5.87 (m, 56 H, CH*), 6.62 (br., 8 H,
CONH), 7.07–8.01 (m, 324 H, Bn, Bz, Py), 8.10 (d, 8 H, Py), 8.21
(s, 8 H, Bn), 8.32 (br., 8 H, Bn), 8.54 (br., 12 H, Bn), 8.84 (br., 8
H, pyrrole β-H), 9.50 (br., 8 H, CONH), 9.96 (br., 8 H, CONH)
ppm. UV/Vis (CHCl3): λmax (ε) = 277.5 (55000), 284 (55000), 302
(53000), 421.5 (109000), 517 (6000), 553 (3000), 592 (2000), 648
(1000) nm.
Complexation of
1
with 8: Dendron
8
(4 equiv., 1.49 mg,
(1.54 mg,
22.52·10–4 mmol) was added to compound
1
5.63·10–4 mmol), suspended in CHCl3 (5 mL, HPLC grade). The
1
solution was stirred at room temp. for 13 h. H NMR (400 MHz,
CDCl3, 25 °C): δ = –2.81 (br., 2 H, pyrrole NH), 0.83–2.43 (m, 88
2
H, CH3, CH2), 3.93 (m, 8 H, CH2N), 5.09 (d, JH,H = 12.0 Hz, 4
H, Bn-CH2), 5.16 (d, 2JH,H = 12.0 Hz, 4 H, Bn-CH2), 5.22 (d, 2JH,H
Complexation of
1 with 12: Dendron 12 (4 equiv., 7.42 mg,
2
= 12.0 Hz, 4 H, Bn-CH2), 5.28 (d, JH,H = 12.0 Hz, 4 H, Bn-CH2),
22.52·10–4 mmol) was added to compound
1
(1.54 mg,
3
3
5.80 (d, JH,H = 2.81 Hz, 4 H, CH*), 5.88 (d, JH,H = 2.81 Hz, 4
H, CH*), 7.06–7.44 (m, 48 H, Bn, Bz), 7.51 (m, 4 H, Bz), 7.84 (t,
5.63·10–4 mmol), suspended in CHCl3 (5 mL, HPLC grade). The
1
solution was stirred at room temp. for 13 h. H NMR (400 MHz,
3JH,H = 7.9 Hz, 8 H, Py), 7.9 (d, JH,H = 7.9 Hz, 8 H, Bz), 8.11 (d,
3
CDCl3, 25 °C): δ = –2.83 (v. br., 2 H, pyrrole NH), 0.84–2.46 (m,
280 H, CH2, CH3), 3.15 (m, 56 H, CH2N), 5.17 (m, 64 H, Bn-
CH2), 5.84 (m, 56 H, CH*), 6.60 (br., 8 H, CONH), 7.06–8.02 (m,
324 H, Bn, Bz; Py), 8.09 (d, 8 H, Py), 8.21 (s, 8 H, Bn), 8.25 (br. 8
H, Bn), 8.53 (m, 12 H, Bn), 8.83 (br., 8 H, pyrrole β-H), 9.44 (br.,
8 H, CONH), 9.95 (br., 8 H, CONH) ppm. UV/Vis (CHCl3): λmax
(ε) = 276.5 (55000), 284.5 (55000), 302.5 (53000), 422 (109000), 517
(6000), 552.5 (3000), 592 (2000), 648.5 (1000) nm.
3J (H,H) = 8.2 Hz, 8 H, Py), 8.13 (d, JH,H = 8.2 Hz, 8 H, Py),
3
8.21 (s, 8 H, Bn), 8.32 (br., 8 H, Bn), 8.52 (br., 8 H, Bn), 8.56 (br.,
4 H, Bn), 8.83 (br., 8 H, pyrrole β-H) 9.48 (br., 8 H, CONH), 9.99
(br., 8 H, CONH) ppm. UV/Vis (CHCl3): λmax (ε) = 302 (98000),
422 (142000), 519 (7000), 552 (4000), 592.5 (2000), 649 (2000) nm.
Complexation of
1
with 9: Dendron
9
(4 equiv., 3.47 mg,
(1.54 mg,
22.52·10–4 mmol) was added to compound
1
5.63·10–4 mmol), suspended in CHCl3 (5 mL, HPLC grade). The
Supporting Information (see footnote on the first page of this arti-
cle): Solubilisation studies concerning the stepwise formation of
complex 18.
1
solution was stirred at room temp. for 13 h. H NMR (400 MHz,
CDCl3, 25 °C): δ = –2.88 (br., 2 H, pyrrole NH), 0.84–2.42 (m, 152
H, CH3, CH2), 3.15 (m, 24 H, CH2N), 3.84 (br., 4 H, CONH), 5.01
2
2
(d, JH,H = 3.1 Hz, 4 H, Bn-CH2), 5.03 (d, JH,H = 3.1 Hz, 4 H,
[1] M. A. Mateos-Timoneda, M. Crego-Calama, D. N. Reinhoudt,
Chem. Soc. Rev. 2004, 33, 363–372.
Bn-CH2), 5.09 (d, 4 H, Bn-CH2), 5.10 (d, 4 H, Bn-CH2), 5.16 (d,
2JH,H = 1.9 Hz, 4 H, Bn-CH2), 5.19 (d, JH,H = 2.7 Hz, 8 H, Bn-
2
[2] a) V. V. Borovkov, J. M. Lintuluoto, Y. Inoue, J. Am. Chem.
Soc. 2001, 123, 2979–2989; b) J.-M. Lehn, Supramolecular
Chemistry: Concepts and Perspectives, VCH, Weinheim, 1995;
c) R. B. Prince, J. S. Moore, L. Brunsveld, E. W. Meijer, Chem.
Eur. J. 2001, 7, 4150–4154; d) A. J. Wilson, M. Masuda, R. P.
Sijbesma, E. W. Meijer, Angew. Chem. 2005, 117, 2315–2319;
Angew. Chem. Int. Ed. 2005, 44, 2275–2279.
2
3
CH2), 5.22 (d, JH,H = 2.8 Hz, 4 H, Bn-CH2), 5.69 (d, JH,H
=
3
3.7 Hz, 4 H, CH*) 5.77 (d, JH,H = 2.8 Hz, 8 H, CH*), 5.79 (d,
3JH,H = 2.8 Hz, 4 H, CH*), 5.88 (d, JH,H = 2.9 Hz, 4 H, CH*),
3
3
5.90 (d, JH,H = 2.8 Hz, 4 H, CH*), 7.06–7.56 (116 H, Bn, Bz),
7.89 (t, 8 H, Py), 7.97 (m,16 H, Bz), 8.00 (m, 24 H, Bz, Py-CH),
3
8.12 (d, JH,H = 7.9 Hz, 8 H, Py-CH), 8.21(s, 8 H, Bn-CH), 8.34
[3] a) I. Sarvary, M. H. Johansson, T. Frejd, CrystEngCommun
2002, 4, 146–148; b) M. R. Ghadiri, J. R. Granja, R. A. Milli-
gan, D. E. McRee, N. Khazanovich, Nature 1993,366, 324–327.
[4] a) L. J. Prins, F. De Jong, P. Timmermann, D. N. Reinhoudt,
Nature 2000, 408, 181–184; b) J. Barberá, L. Puig, P. Romero,
J. L. Serrano, T. Sierra, J. Am. Chem. Soc. 2005, 127, 458–464;
c) L. J. Prins, J. Huskeens, F. de Jong, P. Timmermann, D. N.
Reinhoudt, Nature 1999, 398, 498–502.
[5] V. V. Borovkov, J. M. Lintuluoto, H. Sugeta, M. Fujiki, R.
Arakawa, Y. Inoue, J. Am. Chem. Soc. 2002, 124, 2993–3006.
[6] V. V. Borovkov, J. M. Lintuluoto, Y. Inoue, Org. Lett. 2002, 4,
169–171.
(br., 8 H, Bn-CH), 8.52 (br., 12 H, Bn-CH), 8.85 (br., 8 H, pyrrole
β-H), 9.48 (br., 8 H, CONH), 10.02 (br., 8 H, CONH) ppm. UV/
Vis (CHCl3): λmax (ε) = 303 (53000), 421.5 (117000), 517.5 (6000),
552.5 (3000), 592 (2000), 648 (2000) nm.
Complexation of
1 with 10: Dendron 10 (4 equiv., 3.47 mg,
22.52·10–4 mmol) was added to compound
1
(1.54 mg,
5.63·10–4 mmol), suspended in CHCl3 (5 mL, HPLC grade). The
solution was stirred at room temp. for 13 h. H NMR (400 MHz,
1
CDCl3, 25 °C): δ = –2.88 (br., 2 H, pyrrole NH), 0.85–2.42 (m, 152
H, CH2, CH3), 3.18 (m, 24 H, CH2N), 3.84 (br., 4 H, CONH), 5.01
2
2
[7] R. E. Dickerson, H. R. Drew, B. N. Conner, R. M. Wing, A. V.
Fratini, M. L. Kopka, Science 1982, 216, 475–485.
(d, JH,H = 4.5 Hz, 4 H, Bn-CH2), 5.05 (d, JH,H = 4.5 Hz, 4 H,
2
2
Bn-CH2), 5.09 (d, JH,H = 3.0 Hz, 4 H, Bn-CH2), 5.12 (d, JH,H
=
[8] a) P. R. Ashton, S. E. Boyd, C. L. Brown, S. A. Nepogodiev,
E. W. Meijer, J. F. Stoddart, Chem. Eur. J. 1997, 3, 974–984; b)
H.-T. Chang, C.-T. Chen, T. Kondo, G. Siuzdak, K. B.
Sharpless, Angew. Chem. 1996, 108, 202–206; Angew. Chem.
Int. Ed. Engl. 1996, 35, 182–186; c) H. F. Chow, C. C. Mak,
Tetrahedron Lett. 1996, 37, 5935–5938; d) J. F. G. A. Jansen,
H. W. I. Peerlings, E. M. M. Brabander-van den Berg, E. W.
Meijer, Science 1994, 266, 1226–1229; e) J. A. Kremers, E. W.
2.4 Hz, 4 H, Bn-CH2), 5.16 (d, 2JH,H = 3.1 Hz, 4 H, Bn-CH2), 5.20
2
2
(d, JH,H = 3.8 Hz, 8 H, Bn-CH2), 5.23 (d, JH,H = 3.8 Hz, 4 H,
3
3
Bn-CH2), 5.69 (d, JH,H = 3.7 Hz, 4 H, CH*), 5.78 (d, JH,H
=
3
2.8 Hz, 8 H, CH*), 5.81 (d, JH,H = 2.8 Hz, 4 H, CH*), 5.89 (d,
3JH,H = 2.8 Hz, 4 H, CH*), 5.92 (d, JH,H = 2.8 Hz, 4 H, CH*),
3
6.22 (br., 4 H, CONH), 7.10–7.53 (116 H, Bn, Bz), 7.90 (t, 8 H,
3
Py), 7.92 (m, 16 H, Bz), 8.00(m, 24 H, Bz, Py), 8.11 (d, JH,H
=
3346
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Eur. J. Org. Chem. 2006, 3338–3347