2115
E. Heyer, R. Ziessel
Letter
Synlett
(3) Bürckstümmer, H.; Tulyakova, E. V.; Deppisch, M.; Lenze, M. R.;
Kronenberg, N. M.; Gsaänger, M.; Stolote, M.; Meerholz, K.;
Würthner, F. Angew. Chem. Int. Ed. 2011, 50, 11628.
(4) (a) Chou, Y.-H.; Chang, H.-C.; Liu, C.-L.; Chen, W.-C. Polymer.
Chem. 2015, 6, 341. (b) Lei, T.; Wang, J.-Y.; Pei, J. Acc. Chem. Res.
2014, 47, 1117.
(5) Ning, Z.; Tian, H. Chem. Commun. 2009, 37, 5483.
(6) (a) Cha, H.; Kim, H. N.; An, T. K.; Kang, M. S.; Kwon, S.-K.; Kim,
Y.-H.; Park, C. E. Appl. Mater. Inter. 2014, 6, 15774. (b) Cha, H.;
Kim, H. N.; An, T. K.; Kang, M. S.; Kwon, S.-K.; Kim, Y.-H.; Park, C.
E. Appl. Mater. Inter. 2014, 6, 15774.
(19) (a) Kato, S.-I.; Diederich, F. Chem. Commun. 2010, 46, 1994.
(b) Kato, S. I.; Kivala, M.; Schweizer, W.; Boudon, C.;
Gisselbrecht, J. P.; Diederich, F. Chem. Eur. J. 2009, 15, 8687.
(c) Jarowski, P. D.; Wu, Y.-L.; Boudon, C.; Gisselbrecht, J.-P.;
Gross, M.; Schweizer, W. B.; Diederich, F. Org. Biomol. Chem.
2009, 7, 1312. (d) Reutenauer, P.; Kivala, M.; Jarowski, P. D.;
Boudon, C.; Gisselbrecht, J.-P.; Gross, M.; Diederich, F. Chem.
Commun. 2007, 4898.
(20) Niu, S.; Ulrich, G.; Retailleau, P.; Ziessel, R. Tetrahedron Lett.
2011, 52, 4848.
(21) Esembeson, B.; Scimeca, M. L.; Michinobu, T.; Diederich, F.;
Biaggio, I. Adv. Mater. 2008, 20, 4584.
(7) (a) Hao, Z.; Iqbal, A. Chem. Soc. Rev. 1997, 26, 203. (b) Kaur, M.;
Choi, D. H. Chem. Soc. Rev. 2015, 44, 58.
(22) Yamagata, T.; Kuwabara, J.; Kanbara, T. Eur. J. Org. Chem. 2012,
5282.
(8) (a) Walker, B.; Tamayo, A. B.; Dang, X.-D.; Zalar, P.; Seo, J. H.;
Garcia, A.; Tantiwiwat, M.; Nguyen, T.-Q. Adv. Funct. Mater.
2009, 19, 3063. (b) Bura, T.; Leclerc, N.; Bechara, R.; Lévêque, P.;
Heiser, T.; Ziessel, R. Adv. Energy Mater. 2013, 3, 1118.
(9) (a) Li, Y.; Sonar, P.; Murphy, L.; Hong, W. Energy Environ. Sci.
2013, 6, 1684. (b) Nielsen, C. B.; Turbiez, M.; McCulloch, I. Adv.
Mater. 2013, 25, 1859. (c) Chandran, D.; Lee, K.-S. Macromol.
Res. 2013, 21, 272.
(10) (a) Fischer, G. M.; Ehlers, A. P.; Zumbusch, A.; Daltrozzo, E.
Angew. Chem. Int. Ed. 2004, 126, 10619. (b) Fischer, G. M.;
Isomäki-Krondahl, M.; Göttker-Schnetmann, I.; Daltrozzo, E.;
Zumbusch, A. Chem. Eur. J. 2009, 15, 4857.
(23) (a) Shoji, T.; Ito, S.; Toyota, K.; Yasunami, M.; Morita, N. Chem.
Eur. J. 2008, 14, 8398. (b) Shoji, T.; Higashi, J.; Ito, S.; Okujima, T.;
Yasunami, M.; Morita, N. Chem. Eur. J. 2011, 17, 5116. (c) Shoji,
T.; Maruyama, A.; Yaku, C.; Kamata, N.; Ito, S.; Okujima, T.;
Toyota, K. Chem. Eur. J. 2015, 21, 402.
(24) (a) Shoji, T.; Shimomura, E.; Maruyama, M.; Maruyama, A.; Ito,
S.; Okujima, T.; Toyota, K.; Morita, N. Eur. J. Org. Chem. 2013,
7785. (b) Gautam, P.; Maragani, R.; Misra, R. Tetrahedron Lett.
2014, 55, 6827. (c) Maragani, R.; Misra, R. Tetrahedron 2014, 70,
3390. (d) Misra, R.; Gautam, P. Org. Biomol. Chem. 2014, 12,
5448.
(11) (a) Ftouni, H.; Bolze, F.; Nicoud, J.-F. Dyes Pigm. 2013, 97, 77.
(b) Ftouni, H.; Bolze, F.; de Roquigny, H.; Nicoud, J.-F. Bioconju-
gate Chem. 2013, 24, 942. (c) Zhang, G.; Li, H.; Bi, S.; Song, L.; Lu,
Y.; Zhang, L.; Yu, J.; Wang, L. Analyst 2013, 138, 6163. (d) Zhang,
H.; Song, L.; Bi, S.; Wu, Y.; Yu, J.; Yang, L. Dyes Pigm. 2014, 102,
100. (e) Schmitt, J.; Heitz, V.; Sour, A.; Bolze, F.; Ftouni, H.;
Nicoud, J.-F.; Flamigni, L.; Ventura, B. Angew. Chem. Int. Ed.
2015, 54, 169.
(12) (a) Lin, S.; Liu, S.; Ye, F.; Xu, L.; Zeng, W.; Wang, L.; Li, L.;
Beuerman, R.; Cao, D. Sens. Actuators, B 2013, 182, 176.
(b) Hang, Y.; Yang, L.; Qu, Y.; Hua, J. Tetrahedron Lett. 2014, 55,
6998.
(25) Compound 6: Tetracyanoethylene (41.0 mg, 0.320 mmol,
1.9 equiv) was added to a solution of 5 (144.3 mg, 0.169 mmol)
in 1,2-dichloroethane (25 mL). The reaction medium was
stirred at 40 °C for 87 h, then evaporated to dryness. Purifica-
tion by column chromatography (SiO2, CH2Cl2–petroleum ether,
80:20 to 100:0 with 2% Et3N), followed by recrystallization
(THF–n-pentane) afforded 6 (129.6 mg, 78%) as a black powder.
1H NMR (300 MHz, CDCl3): δ = 0.83–0.91 (m, 12 H), 1.21–1.40
(m, 16 H), 1.78–1.92 (m, 2 H), 3.84 (s, 6 H), 4.00–4.06 (m, 4 H),
6.81 (d, 3J = 9.2 Hz, 2 H), 6.92 (d, 3J = 8.9 Hz, 4 H), 7.16 (d,
3J = 8.9 Hz, 4 H), 7.33 (dd, 3J = 5.0, 4.8 Hz, 1 H), 7.67 (d,
3J = 9.2 Hz, 2 H), 7.77 (dd, 3J = 5.0 Hz, 4J = 1.0 Hz, 1 H), 7.84 (d,
3J = 4.5 Hz, 1 H), 9.06 (d, 3J = 4.5 Hz, 1 H), 9.17 (dd, 3J = 4.1 Hz,
4J = 0.8 Hz, 1 H). 13C NMR (75 MHz, CDCl3): δ = 10.5, 14.1, 23.2,
23.5, 23.6, 28.3, 28.4, 30.1, 30.2, 39.1, 39.8, 46.2, 46.4, 55.7, 80.1,
108.6, 112.0, 113.0, 113.0, 113.1, 113.9, 115.5, 116.8, 120.0,
125.4, 128.3, 129.1, 129.4, 132.1, 133.3, 135.6, 136.0, 137.1,
137.7, 138.1, 140.2, 144.4, 154.8, 157.5, 158.5, 161.0, 161.9,
162.1. UV/Vis (toluene): λ (ε, M–1cm–1) = 691 (37 200), 636
(27 300), 483 (31 500), 333 (16 000) nm. MS (EI): m/z (%) calcd
for C58H57N7O4S2: 979.39 (100); found 979.2 (100), 953.2 (25).
Anal. Calcd for C58H57N7O4S2 (980.25): C, 71.07; H, 5.86, N,
10.00. Found: C, 70.84; H, 5.47; N, 9.77.
(26) Compound 8: Tetracyanoethylene (23.3 mg, 0.182 mmol,
3.4 equiv) was added to a solution of 7 (64.2 mg, 0.054 mmol)
in 1,2-dichloroethane (15 mL). The reaction medium was
stirred at 40 °C for 18 h, then evaporated to dryness. Purifica-
tion by column chromatography (Al2O3; CH2Cl2–petroleum
ether, 70:30 to 80:20), followed by recrystallization (THF–n-
pentane) afforded 8 (41.6 mg, 54%) as a brownish black powder.
1H NMR (300 MHz, CDCl3): δ = 0.83–0.91 (m, 12 H), 1.21–1.36
(m, 16 H), 1.78–1.84 (m, 2 H), 3.82 (s, 12 H), 4.02 (d, 3J = 7.9 Hz,
4 H), 6.81 (d, 3J = 9.2 Hz, 4 H), 6.91–6.95 (m, 8 H), 7.13–7.18 (m,
8 H), 7.66 (d, 3J = 9.4 Hz, 4 H), 7.85 (d, 3J = 4.6 Hz, 2 H), 9.20 (d,
3J = 4.6 Hz, 2 H). 13C NMR (75 MHz, CDCl3): δ = 10.4, 14.1, 23.2,
23.4, 28.2, 30.0, 39.7, 46.6, 55.7, 76.5, 81.8, 111.6, 112.7, 112.9,
113.1, 113.8, 115.5, 116.9, 119.8, 128.3, 132.1, 137.1, 137.3,
137.7, 138.8, 139.0, 140.0, 154.9, 157.7, 158.6, 161.1, 161.6.
(13) Shen, H.; Kou, C.; He, M.; Yang, H.; Liu, K. J. Polym. Sci., Part A:
Polym. Chem. 2014, 52, 739.
(14) For selected recent examples, see: (a) Schmidt, C. D.; Hirsch, A.
In Ideas in Chemistry and Molecular Sciences: Advances in Syn-
thetic Chemistry; Pignataro, B., Ed.; Wiley-VCH: Weinheim,
2010, 283. (b) Traoré, T.; Clavé, G.; Delacour, L.; Kotera, N.;
Renard, P.-Y.; Romieu, A.; Berthault, P.; Boutin, C.; Tassali, N.;
Rousseau, B. Chem. Commun. 2011, 47, 9702. (c) Cole, E. L.;
Arunkumar, E.; Xiao, S.; Smith, B. A.; Smith, B. D. Org. Biomol.
Chem. 2012, 10, 5769. (d) Jiang, J.; Vairaprakash, P.; Reddy, K. R.;
Sahin, T.; Pavan, M. P.; Lubian, E.; Lindsey, J. S. Org. Biomol.
Chem. 2014, 12, 86. (e) Thomas, A. W.; Henson, Z. B.; Du, J.;
Vandenberg, C. A.; Bazan, G. C. J. Am. Chem. Soc. 2014, 136, 3736.
(f) Wiktorowski, S.; Rosazza, C.; Winterhalder, M. J.; Daltrozzo,
E.; Zumbusch, A. Chem. Commun. 2014, 50, 4755. (g) Bernhard,
Y.; Winckler, P.; Chassagnon, R.; Richard, P.; Gigot, E.; Perrier-
Cornet, J.-M.; Decreau, R. A. Chem. Commun. 2014, 50, 13975.
(15) Hablot, D.; Retailleau, P.; Ziessel, R. Chem. Eur. J. 2010, 16,
13346.
(16) Mula, S.; Hablot, D.; Jagtap, K. K.; Heyer, E.; Ziessel, R. New J.
Chem. 2013, 37, 303.
(17) Heyer, E.; Lory, P.; Leprince, J.; Moreau, M.; Romieu, A.;
Guardigli, M.; Roda, A.; Ziessel, R. Angew. Chem. Int. Ed. 2015, 54,
2995.
(18) Huo, L.; Hou, J.; Chen, H.-Y.; Zhang, S.; Jiang, Y.; Chen, T. L.; Yang,
Y. Macromolecules 2009, 42, 6564.
© Georg Thieme Verlag Stuttgart · New York — Synlett 2015, 26, 2109–2116