A Two-Step Synthesis of Quarterrylene Bisimides: Application of the ‘Green Route’ Method

Abstract

Perylene-3,4:9,10-tetracarboxylic-3,4-anhydride-9,10-imides have been transformed in one-step into bichromophoric 9,9′-bis(perylene-3,4-dicarboximide)s by reaction with copper powder, 3-methylpyridine, and oxygen, and further to quaterrylene bis­imides with potassium tert-butoxide and DBN. Quaterrylene bis­imides are of interest as NIR fluorescent dyes.

Key words

quaterrylene - dyes - green route - copper - polycyclic aromatics­

References

• 1 Daehne S. Resch-Genger U. Wolfbeis O. Near-Infrared Dyes for High Technology Applications   1st ed.:  Kluwer Academic Publishers; Dordrecht: 1998. 
• 2 Langhals H. Schönmann G. Feiler L. Tetrahedron Lett.  1995,  36:  6423 
• 3 Quante H. Müllen K. Angew. Chem. Int. Ed. Engl.  1995,  43:  1323 ; Angew. Chem. 1995, 107, 1487
• 4 Lee KS. Zu Y. Herrmann A. Geerts Y. Müllen K. Bard AJ. J. Am. Chem. Soc.  1999,  121:  3513 
• 5 Adachi M. Nagao Y. Chem. Mater.  2001,  13:  662 
• 6 Clar E. Polycyclic Hydrocarbons   1st ed.:  Academic Press; London: 1964. 
• 7 Langhals H. Süßmeier F. J. Prakt. Chem.  1999,  341:  309 
• 8 Tröster H. Dyes Pigm.  1983,  4:  171 
• 9 Kaiser H. Lindner J. Langhals H. Chem. Ber.  1991,  124:  529 
• 10 Süßmeier F. Langhals H. Eur. J. Org. Chem.  2001,  607 
• 11 Geerts Y. Quante H. Platz H. Mahrt R. Hopmeier M. Bohm A. Müllen K. J. Mater. Chem.  1998,  8:  2357 
• 12 Tam-Chang S.-W. Seo W. Iverson IK. J. Org. Chem.  2004,  69:  2719 
• 13 Sakamoto T. Pac C. J. Org. Chem.  2001,  66:  94 
• 14 Langhals H. Demmig S. Potrawa T. J. Prakt. Chem.  1991,  333:  733 
• 15 Langhals H. Karolin J. Johansson LB.-Å. J. Chem. Soc., Faraday Trans.  1998,  94:  2919 
• 16 Shreiner RL. Neumann FW. Org. Synth., Coll. Vol. III   Wiley; New York: 1955.  p.74 
• 17 Fieser M. Fieser LF. Reagents for Organic Synthesis   Vol. 3:  Wiley-Interscience; New York: 1972.  p.334