The first intramolecular charge transfer transition based on 2-ureido-4[1 H]-pyrimidinone binding module
Chun-Chang Zhao
Technical Institute of Physics and Chemistry, Chinese Academy of Science, Beijing 100101, China
Search for more papers by this authorZhan-Tng Li
Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032, China
Search for more papers by this authorLi-Zhu Wu
Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032, China
Search for more papers by this authorLi-Ping Zhang
Technical Institute of Physics and Chemistry, Chinese Academy of Science, Beijing 100101, China
Search for more papers by this authorChen-Ho Tung
Technical Institute of Physics and Chemistry, Chinese Academy of Science, Beijing 100101, China
Search for more papers by this authorChun-Chang Zhao
Technical Institute of Physics and Chemistry, Chinese Academy of Science, Beijing 100101, China
Search for more papers by this authorZhan-Tng Li
Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032, China
Search for more papers by this authorLi-Zhu Wu
Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032, China
Search for more papers by this authorLi-Ping Zhang
Technical Institute of Physics and Chemistry, Chinese Academy of Science, Beijing 100101, China
Search for more papers by this authorChen-Ho Tung
Technical Institute of Physics and Chemistry, Chinese Academy of Science, Beijing 100101, China
Search for more papers by this authorAbstract
The first intramolecular charge transfer transition based on 2-ureido- 4[1H]-pyrimidinone binding module was reported.
References
- 1(a) Sijbesma, R. P.; Meijer, E. W. Chem. Commun. 2003, 5. (b) Brunsveld, L.; Folmer, J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071. (c) Schmick, C.; Wienand, W. Angew. Chem, Int. Ed. 2001, 40, 4363. (d) Conn, M. M.; Rebek, J. Chem Rev. 1997, 97, 1647.
- 2(a) Corbin, P. S.; Lawless, L. J.; Li, Z.-T.; Ma, Y.; Witmer, M. J.; Zimmerman, S. C. Proc. Nat. Acad. Sci. USA 2002, 99, 5099. (b) Corbin, P. S.; Zimmerman, S. C.; Thiessen, P. A.; Hawryluk, N. A.; Murray, T. J. J. Am. Chem. Soc. 2001, 123, 10475. (c) Gong, B.; Yan, Y.; Zeng, H.; Skrzypczak-Jankunm, E.; Kim, Y. W.; Zhu, J.; Iches, H. J. Am. Chem. Soc. 1999, 121, 5607.
- 3(a)
Beijer, F. H.;
Sijbesma, R. P.;
Kooijman, H.;
Spek, A. L.;
Meijer, E. W.
J. Am. Chem. Soc.
1998,
120, 6761, and references therein.
(b)
Söntjens, S. H. M.;
Sijbesma, R. P.;
van Genderen, M. H. P.;
Meijer, E. W.
J. Am Chem. Soc.
2000,
122, 7487.
(c)
Wang, X.-Z.;
Li, X.-Q.;
Shao, X.-B.;
Zhao, X.;
Deng, P.;
Jiang, X.-K.;
Li, Z.-T.;
Chen, Y.-Q.
Chem. Eur. J.
2003,
9, 2904.
(d)
Shao, X.-B.;
Jiang, X.-K.;
Zhao, X.;
Chen, Y.;
Li, Z.-T.
J. Org. Chem
2004,
69, 899.
(e)
Rispens, M. T.;
Sánchez, L.;
Knol, J.;
Hummelen, J. C.
Chem. Commun.
2001, 161.
(f)
El-ghayoury, A.;
Peeters, E.;
Schenning, A. P. H. J.;
Meijer, E. W.
Chem Commun.
2000, 1969.
(g)
Sánchez, L.;
Rispens, M. T.;
Hummelen, J. C.
Angew. Chem., Int. Ed.
2002,
41, 838.
10.1002/1521-3773(20020301)41:5<838::AID-ANIE838>3.0.CO;2-F CAS PubMed Web of Science® Google Scholar(h) Söntjens, S. H. M.; van Genderen, M. H. P.; Meijer, E. W. J. Am. Chem. Soc. 2000, 122, 7487.
- 4(a) Ikegam, M.; Arai, T. Chem. Lett. 2001, 694. (b) Neuteboom, E. E. N.; Bechers, E. H. A.; Meskers, S. C. J.; Meijer, E. W.; Janssen, R. A. J. Org. Biomol. Chem. 2003, 1, 198. (c) Zhao, C.-C.; Tong, Q.-X.; Li, Z.-T.; Wu, L.-Z.; Zhang, L.-P.; Tung, C.-H. Tetrahedron Lett. 2004, 45, 6807.
- 5 Compound 1: 1H NMR (CDCl3, 400 MHz) Δ: 13.95 (s. 1H), 12.25 (s, lH), 10.44 (s, 1H), 7.72 (d, J=6.9 Hz, 2H), 6.93 (d, J=8.9 Hz, 2H), 6.42 (s, lH), 3.47–3–.45 (m, 2H), 3.21 (s. 6H), 1.79–1–.77 (m, 2H), 1.59–1–.55 (m, 2H), 1.11 (t, 3=7.3 Hz, 3H), Anal. calcd for C17H23N5O2: C 61.99, H 7.04, N 21.26; found C 61.87, H 6.98, N 21.17. Compound 2: 1H NMR (CDCl3, 400 MHz) Δ: 12.86 (s, 1H), 11.92 (s, 1H). 10.19 (s, lH), 7.14 (d, J=8.4 Hz, 2H), 6.67 (d, J=6.4 Hz, 2H), 3.71 (s, 2H), 3.22–3–.27 (m, 2H), 2.90 (s, 6H), 2.23 (s, 3H), 1.54–1–.62 (m, 2H), 1.36–1–.42 (m, 2H), 0.93 (t, J=7.3 Hz, 3H), 13C NMR (CDCl3, 400 MHz) Δ: 172.6, 156.9, 153.3, 149.3, 143.9, 129.1, 128.2, 118.1, 113.1, 41.0, 39.8, 31.4, 29.7, 20.3, 17.5, 13.9. Anal. caled for C19H27N5O2: C 63.84, H 7.61, N 19.59; found C 63.77, H 7.64, N 19.63.
- 6 Reichardt, C. Angew. Chem, Int. Ed Engl. 1979, 18, 98.
- 7 Jones, G. II.; Jackson, W. R.; Choi, C.; Bergmark, E. R. J. Phys. Chem. 1985, 89, 294.
- 8(a) Mataga, N.; Kaifu, Y.; Koizumi, M. Bull. Chem. Soc. Jpn. 1995, 28, 690. (b) Ramakrishna, G.; Ghosh, H. N. J. Phys. Chem 2002, 106, 2545.
- 9(a) Lippert, E.; Rettig, W.; Bonacic-koutecky, V.; Heisel, F.; Miehe, J. A. Adv. Chem. Phys. 1987, 68, 1. (b) Rettig, W.; Wermuth, G. J. Photochem 1985, 28, 351.