Organic Letters
Letter
(
3
(
9) Wu
037.
10) The synthesis of tetraheptyl 1,6,7,12-tetrachloroperylene-
̈
rthner, F.; Sautler, A.; Schilling, J. J. Org. Chem. 2002, 67,
ASSOCIATED CONTENT
■
*
S
Supporting Information
Experimental procedures and full characterization data. This
3,4,9,10-tetracarboxylate was recently reported; see: Zagranyarski, Y.;
Chen, L.; Jansch, D.; Gessner, T.; Li, C.; Mullen, K. Org. Lett. 2014,
1
6, 2814.
(11) Hassheider, T.; Benning, S. A.; Kitzerow, H. S.; Achard, M. F.;
Bock, H. Angew. Chem., Int. Ed. 2001, 40, 2060.
(12) NMR spectra were taken at different concentrations, which may
explain the slightly different chemical shifts.
AUTHOR INFORMATION
■
*
(13) Qian, H.; Liu, C.; Wang, Z.; Zhu, D. Chem. Commun. 2006,
4
587.
Notes
(14) Kaiser, H.; Lindner, J.; Langhals, H. Chem. Ber. 1991, 124, 529.
(
15) Zagranyarski, Y.; Chen, L.; Zhao, Y.; Wonneberger, H.; Li, C.;
Mullen, K. Org. Lett. 2012, 14, 5444.
16) Langhals, H.; Karolin, J.; Johansson, L. B.-Å. J. Chem. Soc.,
Faraday Trans. 1998, 94, 2919.
The authors declare no competing financial interest.
̈
(
ACKNOWLEDGMENTS
■
We thank Tshego Epema, Sanne Nielsen, Joost Nijskens,
Maikel Rutten, Walter Starmans, and Youri van Uum from
Delft University for their contribution. Brijith Thomas from
Leiden University is kindly acknowledged for recording 850
1
MHz H NMR spectra. This project was carried out within the
research programme of BioSolar Cells, cofinanced by the Dutch
Ministry of Economic Affairs, Agriculture and Innovation.
REFERENCES
■
(
2
1) (a) Huang, C.; Barlow, S.; Marder, S. R. J. Org. Chem. 2011, 76,
386. (b) Wu
̈
rthner, F. Chem. Commun. 2004, 1564. (c) Weil, T.;
llen, K. Angew. Chem., Int. Ed.
rl, D.; Zhang, X.; Wurthner, F. Angew. Chem.,
Int. Ed. 2012, 51, 6328. (e) Li, C.; Wonneberger, H. Adv. Mater. 2012,
4, 613. (f) Zollinger, H. Color Chemistry, 3rd ed.; VHCA and Wiley-
VCH: Zurich, Weinheim, 2003. (g) Langhals, H. Helv. Chim. Acta
005, 88, 1309.
2) (a) Nakazono, S.; Imazaki, Y.; Yoo, H.; Yang, J.; Sasamori, T.;
Vosch, T.; Hofkens, J.; Peneva, K.; Mu
̈
2
010, 49, 9068. (d) Go
̈
̈
2
̈
2
(
Tokitoh, N.; Cedric, T.; Kageyama, H.; Kim, D.; Shinokubo, H.;
Osuka, A. Chem.Eur. J. 2009, 15, 7530. (b) Nakazono, S.;
Easwaramoorthi, S.; Kim, D.; Shinokubo, H.; Osuka, A. Org. Lett.
2
009, 11, 5426.
(
3) Bay area halogenations of PBIs and perylenetetraesters (PTEs)
have been reported also, but here our focus is on the more universal
halogenation of PBA.
(
4) Bo
German Pat. DE 19547209 A1, 1997.
̈
5) (a) Wurthner, F.; Stepanenko, V.; Chen, Z.; Saha-Moller, C. R.;
̈
hm, A.; Arms, H.; Henning, G.; Blaschka, P. (BASF AG)
(
̈
Kocher, N.; Stalke, D. J. Org. Chem. 2004, 69, 7933. (b) Dubey, R. K.;
Efimov, A.; Lemmetyinen, H. Chem. Mater. 2011, 23, 778. (c) Dubey,
R. K.; Niemi, M.; Kaunisto, K.; Efimov, A.; Tkachenko, N. V.;
Lemmetyinen, H. Chem.Eur. J. 2013, 19, 6791. (d) Sengupta, S.;
Dubey, R. K.; Hoek, R. W. M.; van Eeden, S. P. P.; Gunbas ,̧ D. D.;
Grozema, F. C.; Sudho
655.
6) (a) Rogovik, V. I.; Gutnok, L. F. J. Org. Chem. USSR 1988, 24,
69. (b) Sadrai, M.; Hadel, L.; Sauers, R. R.; Hussain, S.; Krogh-
Jespersen, K.; Westbrook, J. D.; Bird, G. R. J. Phys. Chem. 1992, 96,
988. (c) Baggerman, J.; Jagesar, D. C.; Vallee, R. A. L.; Hofkens, J.;
Schryver, F. C. D.; Schelhase, F.; Vo
̈
lter, E. J. R.; Jager, W. F. J. Org. Chem. 2014, 79,
6
(
5
7
́
̈
gtle, F.; Brouwer, A. M. Chem.
Eur. J. 2007, 13, 1291. (d) Queste, M.; Cadiou, C.; Pagoaga, B.;
Giraudet, L.; Hoffmann, N. New J. Chem. 2010, 34, 2537. (e) Sukul, P.
K.; Datta, A.; Malik, S. Chem.Eur. J. 2014, 20, 3019.
(
̈
̈
7) (a) Abdalla, M. A.; Bayer, J.; Radler, J. O.; Mullen, K. Angew.
Chem., Int. Ed. 2004, 43, 3967. (b) Martín, R.; Ces
Miguel, M. D.; Fernandez-Lazaro, F.; García, H.; Sastre-Santos, A.
Chem. Sci. 2012, 3, 470. (c) You, C.-C.; Hippius, C.; Grune, M.;
Wu pedes-Guirao, F.
rthner, F. Chem.Eur. J. 2006, 12, 7510. (d) Ces
J.; Ropero, A. B.; Font-Sanchis, E.; Nadal, A.; Fernandez-Lazaro, F.;
́
pedes-Guirao, F. J.;
́
́
́
̈
̈
́
́
́
́
́
Sastre-Santos, A. Chem. Commun. 2011, 47, 8307.
(
8) Nia, A. S.; Enders, C.; Binder, W. H. Tetrahedron 2012, 68, 722.
1
885
Org. Lett. 2015, 17, 1882−1885