Synthesis of water-soluble perylene dicarboximide derivatives containing pyridine oxide groups

Synthetic Communications

Volumn 42, Issue 10, 2012, Pages 1472-1479

  Sun, Juanjuan ^a   Wang, Ming ^a   Xu, Ping ^a   Zhang, Shuai ^a   Shi, Zhiqiang ^a  

^a SHANDONG NORMAL UNIVERSITY   (China)

Author keywords

Fluorescence; Perylene diimides; Pyridine N oxide; Water soluble chromophore

Indexed keywords

IMIDE; PERYLENE; PERYLENE DICARBOXIMIDE DERIVATIVE; PYRIDINE 1 OXIDE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL COMPOSITION; CHROMATOPHORE; SOLUBILITY; SYNTHESIS;

EID: 84863168723     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.540731     Document Type: Article

References (16)

1. Ping, C.; Shuqing, S.; Yunfeng, H.; Zhiguo, Q.; Deshui, Z. Structure and solvent effect on the photostability of indolenine cyanine dyes. Dyes Pigm. 1999, 41, 227-231.
2. Fischer, M.; Georges, J. Fluorescence quantum yield of rhodamine 6G in ethanol as a function of concentration using thermal lens spectrometry. Phys. Lett. 1996, 260, 115-118. (Pubitemid 126161537)
3. Nagao, Y.; Misono, T. Synthesis and properties of N-alkyl-N′-aryl- 3,4:9,10-perylenebis (dicarboximide). Dyes Pigm. 1984, 5, 171-188.
4. Christie, R. M. Pigments, dyes, and fluorescent brightening agents for plastics: An overview. Polym. Int. 1994, 34, 351-361.
5. Anthony, J. E.; Facchetti, A.; Heeney, M.; Marder, S. R.; Zhan, X. n-Type organic semiconductors in organic electronics. Adv. Mater. 2010, 22, 3876-3892.
6. Zhan, X.; Tan, Z.; Domercq, B.; An, Z.; Zhang, X.; Barlow, S.; Li, Y.; Zhu, D.; Kippelen, B.; Marder, S. R. A high-mobility electron-transport polymer with broad absorption and its use in field-effect transistors and all-polymer solar cells. J. Am. Chem. Soc. 2007, 129, 7246-7247. (Pubitemid 46980790)
7. Würthner, F. Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures. Chem.Commun. 2004, 1564-1579. (Pubitemid 39089105)
8. Wasielewski, M. R. Energy, charge, and spin transport in molecules and self-assembled nanostructures inspired by photosynthesis. J. Org. Chem. 2006, 71, 5051-5066.
9. Jianqiang, Q.; Christopher, K.; Mark, P.; Mullen, K. Ionic perylenetetracarboxdiimides: Highly fluorescent and water-soluble dyes for biolabeling. Angew. Chem. Int. Ed. 2004, 43, 1528-1531. (Pubitemid 39257891)
10. Nobuaki, S.; Tomoyuki, A.; Tuyoshi, F.; Hizuru, N.; Koji, N.; Toshihiko, I. Swallow-tailed perylene derivative: A new tool for fluorescent imaging of lipid hydroperoxides. Org. Biomol. Chem. 2007, 5, 3762-3768.
11. Schnurpfeil, G.; Stark, J.; Wöhrle, D. Syntheses of uncharged, positively and negatively charged 3,4,9,10-perylene-bis(dicarboximides). Dyes Pigm. 1995, 27, 339-350.
12. Langhals, H. Water-soluble perylenetetracarboxylic acid bisimide fluorescent dyes. Germany Patent 3703513, February 5, 1987.
13. Langhals, H.; Jona, W.; Einsiedl, F.; Wohnlich, S. Self-dispersion: Spontaneous formation of colloidal dyes in water. Adv. Mater. 1998, 10, 1022-1024. (Pubitemid 128536029)
14. Weil, T.; Abdallah, M.; Jatzke, C.; Hengstler, J.; Mü llen, K. Water-soluble rylene dyes as high-performance colorants for the staining of cells. Biomacromolecules 2005, 6, 68-79. (Pubitemid 40277001)
15. Klok, H. A.; Hernandez, J. R.; Becker, S.; Mü llen, K. Star-shaped fluorescent polypeptides. J. Polym. Sci. A. 2001, 39, 1572-1583. (Pubitemid 32450542)
16. Würthner, F.; Sautter, A.; Schmid, D.; Weber, P. J. A. Fluorescent and electroactive cyclic assemblies from perylene tetracarboxylic acid bisimide ligands and metal phosphane triflates. Chem. Eur. J. 2001, 7, 894-902. (Pubitemid 32182658)