Versatile colorant syntheses by multiple condensations of acetyl anilines with perylene anhydrides

Angewandte Chemie - International Edition

Volumn 54, Issue 7, 2015, Pages 2285-2289

  Jänsch, Daniel ^a   Li, Chen ^a   Chen, Long ^a,b   Wagner, Manfred ^a   Müllen, Klaus ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^b TIANJIN UNIVERSITY   (China)

Author keywords

Aldol condensations; Heterocyclic compounds; Naphthalenes; Perylenes; Rearrangements

Indexed keywords

ANILINE; CHROMOPHORES; CONDENSATION; ELECTRON TRANSITIONS; ELECTRONIC PROPERTIES; KETONES; NAPHTHALENE; POLYCYCLIC AROMATIC HYDROCARBONS;

ALDOL CONDENSATION; CARBONYL GROUPS; FUNCTIONALIZATIONS; HETEROCYCLIC COMPOUND; MALONONITRILES; OPTICAL AND ELECTRONIC PROPERTIES; PERYLENES; REARRANGEMENTS;

CONDENSATION REACTIONS;

EID: 85027918295     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201409634     Document Type: Article

References (37)

1. rd ed., Wiley-VCH, Weinheim, 2006 ;
2. b) A. Herrmann, K. Müllen, Chem. Lett. 2006, 35, 978-985.
3. F. Würthner, Chem. Commun. 2004, 1564-1579.
4. C. Huang, S. Barlow, S. R. Marder, J. Org. Chem. 2011, 76, 2386-2407.
5. a) C.W. Tang, Appl. Phys. Lett. 1986, 48, 183-185;
6. b) C. Li, H. Wonneberger, Adv. Mater. 2012, 24, 613-636;
7. A. Mishra, K. R. Fischer, P. Bäuerle, Angew. Chem. Int. Ed. 2009, 48, 2474 -2499;
8. Angew. Chem. 2009, 121, 2510-2536.
9. M. Kardos, Deutsches Reichspatent No. 276357, 1913.
10. a) J. Feng, B. Liang, D. Wang, L. Xue, X. Li, Org. Lett. 2008, 10, 4437-4440;
11. b) K. J. Thorley, F. Würthner, Org. Lett. 2012, 14, 6190-6193;
12. c) N. Buffet, É. Grelet, H. Bock, Chem. Eur. J. 2010, 16, 5549-5553;
13. d) Y. Li, G. Zhang, G. Yang, Y. Guo, C. Di, X. Chen, Z. Ziu, H. Liu, Z. Xu, W. Xu, H. Fu, D. Zhang, J. Org. Chem. 2013, 78, 2926-2934.
14. a) H. Quante, Y. Geerts, K. Müllen, Chem. Mater. 1997, 9, 495-500;
15. b) M. Mamada, P. Anzenbacher, Org. Lett. 2011, 13, 4882-4885;
16. c) M. Mamada, C. P. Bolívar, D. Kumaki, N. A. Esipenko, S. Tokito, P. Anzenbacher, Chem. Eur. J. 2014, 20, 11835-11846.
17. a) C. Lütke Eversloh, C. Li, K. Müllen, Org. Lett. 2011, 13, 4148-4150;
18. )W. Jiang, Y. Li,W. Yue, Y. Zhen, J. Qu, Z. Wang, Org. Lett. 2010, 12, 228;
19. c) S. Müller, K. Müllen, Chem. Commun. 2005, 4045-4046;
20. d) S. Alibert-Fouet, I. Seguy, J.-F. Bobo, P. Destruel, H. Bock, Chem. Eur. J. 2007, 13, 1746-1753.
21. F. Holtrup, G. Müller, H. Quante, S. de Feyter, F. C. De Schryver, K. Müllen, Chem. Eur. J. 1997, 3, 219-225.
22. H. Quante, K. Müllen, Angew. Chem. Int. Ed. Engl. 1995, 34, 1323 - 1325;
23. Angew. Chem. 1995, 107, 1487-1489.
24. Z. Yuan, S.-L. Lee, L. Chen, C. Li, K. S. Mali, S. De Feyter, K. Müllen, Chem. Eur. J. 2013, 19, 11842-11846.
25. a) H.-S. Bien, J. Stawitz K. Wunderlich in Anthraquinone Dyes and Intermediates. Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2000 ;
26. b) T. Sawada, H. Ishii, Y. Aoyama, T. Ueda, J. Aoki, M. Takekawa, Synth. Commun. 2012, 42, 784-793;
27. c) D.-V. Tinh, M. Fischer, W. Stadlbauer, J. Heterocycl. Chem. 1996, 33, 905-910;
28. d) L. Li, C. S. B. Gomes, P. T. Gomes, T. Pedro, T. M. Duarte, Synth. Commun. 2008, 38, 4415-4425.
29. H. Z. Alkhathlan, J. Chem. Res. Synop. 1992, 260-261.
30. D. Gosztola, M. P. Niemczyk, W. Svec, A. S. Lukas, M. R. Wasielewski, J. Phys. Chem. A 2000, 104, 6545-6551.
31. H. Quante, Ph. D. thesis, University of Mainz (Germany), 1995.
32. D. M. McKinnon, J. Y. Wong, Can. J. Chem. 1971, 49, 2018-2022.
33. a) P. Friedländer, Ber. Dtsch. Chem. Ges. 1882, 15, 2572;
34. b) J. Marco-Contelles, E. Pérez-Mayoral, A. Samadi,M. Carreiras, E. Soriano, Chem. Rev. 2009, 109, 2652-2671.
35. a) A. Böhm,W. Helfer, DE 19501737, 1996 ;
36. b) M. Könemann, P. Blaschka, H. Reichelt, DE 102004054303, 2006;
37. c) K. Tomizaki, P. Thamyongkit, R. S. Loewe, J. S. Lindsey, Tetrahedron 2003, 59, 1191-1207.