The Synthesis of Azaperylene-9,10-dicarboximides

 

 Buy Article Permissions and Reprints All articles of this category

Abstract

The syntheses of two azaperylene 9,10-dicarboximides are presented. 1-Aza- and 1,6-diazaperylene 9,10-dicarboximides containing a 2,6-diisopropylphenyl substituent at the N-imide position were synthesized in two steps starting from naphthalene and isoquinoline derivatives.

References and Notes

• 1a Zollinger H. Color Chemistry   3rd ed.:  Wiley-VCH; Weinheim: 2003. 
  Google Scholar
• 1b Würthner F. Chem. Commun.  2004,  1564 
  Google Scholar
• 2a Zhan X. Tan Z. Domercq B. An Z. Zhang X. Barlow S. Li Y. Zhu D. Kippelen B. Marder SR.
  J. Am. Chem. Soc.  2007,  129:  7246 
  Google Scholar
• 2b Schmidt-Mende L. Fechtenkötter A. Müllen K. Moons E. Friend RH. MacKenzie JD. Science  2001,  293:  1119 
  Google Scholar
• 2c Yakimov A. Forrest SR. Appl. Phys. Lett.  2002,  80:  1667 
  Google Scholar
• 2d Shin WS. Jeong H.-H. Kim M.-K. Jin S.-H. Kim M.-R. Lee J.-K. Lee JW. Gal Y.-S. J. Mater. Chem.  2006,  16:  384 
  Google Scholar
• 3 Sadrai M. Hadel L. Sauers RR. Husain S. Krogh-Jespersen K. Westbrook JD. Bird FR. J. Phys. Chem.  1992,  96:  7988 
  CrossrefGoogle Scholar
• 4 Ego C. Marsitzky D. Becker S. Zhang J. Grimsdale AC. Müllen K. MacKenzie JD. Silva C. Friend RH. J. Am. Chem. Soc.  2003,  125:  437 
  CrossrefGoogle Scholar
• 5 O’Neil MP. Niemczyk MP. Svec WA. Gosztola D. Gaines GL. Wasielewski MR. Science  1992,  257:  63 
  CrossrefGoogle Scholar
• 6 Feiler L. Langhals H. Polborn K. Liebigs Ann.  1995,  1229 
  CrossrefGoogle Scholar
• 7 Rachford AA. Goeb S. Castellano FN. J. Am. Chem. Soc.  2008,  130:  2766 
  CrossrefGoogle Scholar
• 8 Weissman H. Shirman E. Ben-Moshe T. Cohen R. Leitus G. Shimon LJW. Rybtchinski B. Inorg. Chem.  2007,  46:  4790 
  CrossrefGoogle Scholar
• 9a Baldo MA. Thompson ME. Forrest SR. Nature (London)  2000,  403:  750 
  Google Scholar
• 9b Brooks J. Babayan Y. Lamansky S. Djurovich PI. Tsyba I. Bau R. Thompson ME. Inorg. Chem.  2002,  41:  3055 
  Google Scholar
• 9c Tsuboyama A. Iwawaki H. Furugori M. Mukaide T. Kamatani J. Igawa S. Moriyama T. Miura S. Takiguchi T. Okada S. Hoshino M. Ueno K. J. Am. Chem. Soc.  2003,  125:  12971 
  Google Scholar
• 9d Chassot L. von Zelewsky A. Inorg. Chem.  1987,  26:  2814 
  Google Scholar
• 9e Thomas SW. Venkatesan K. Müller P. Swager TM. J. Am. Chem. Soc.  2006,  128:  16641 
  Google Scholar
• 10 Gryko DT. Piechowska J. Galūzowski M. J. Org. Chem.  2010,  75:  1297 
  CrossrefGoogle Scholar
• 11a Jiao C. Huang K.-W. Luo J. Zhang K. Chi C. Wu J. Org. Lett.  2009,  11:  4508 
  Google Scholar
• 11b Yao JH. Chi C. Wu J. Loh K.-P. Chem. Eur. J.  2009,  15:  9299 
  Google Scholar
• 12 Nolde F. Qu J. Kohl C. Pschirer NG. Reuther E. Müllen K. Chem. Eur. J.  2005,  11:  3959 
  CrossrefGoogle Scholar
• 13 Weil T. Reuther E. Beer C. Müllen K. Chem. Eur. J.  2004,  10:  1398 
  CrossrefGoogle Scholar
• 14 1-Chloroisoquinoline is a commercial compound. Triflate 6 was synthesized from 8-hydroxyisoquinoline, following: Yoshida Y. Barrett D. Azami H. Morinaga C. Matsumoto S. Matsumoto Y. Takasugi H. Bioorg. Med. Chem.  1999,  7:  2647 
  CrossrefGoogle Scholar
• 15 Chloride 9 was synthesized by POCl₃ treatment of 2,7-naphthyridine-1-one, which was synthesized following: Zhang A. Ding CY. Cheng C. Yao QZ. J. Comb. Chem.  2007,  9:  916 
  CrossrefPubMedGoogle Scholar
• 16 Sakamoto T. Pac C. J. Org. Chem.  2001,  66:  94 
  CrossrefGoogle Scholar

• Supplementary Material