N,N-Bis(1-butylpentyl)-3,4:9,10-perylenebis(dicarboximide);
2,9-bis-(1-butylpentyl)anthra[2,1,9-def;6,5,10-def]diisoquinoline-1,3,8,10(2H,9H)-tetraone; 2,9-bis-(5-nonyl)anthra[2,1,9-def;6,5,10-def]diisoquinoline-1,3,8,10(2H,9H)-tetraone, RN 110613-98-4:
M.p. 268°C, bright red crystals. UV (CHCl3): λmax
(ε) = 458 nm (18660), 488.5 (51640), 524.5 (85510). C42H46N2O4 (642.8) calcd. C 78.47, H 7.21, N 4.36; found C 78.58, H 7.13, N 4.18.
References, RN 110613-98-4:
*1. Demmig, S.; Langhals, H. Very soluble and photostable perylene fluorescent dyes, Chem. Ber. 1988, 121, 225-230.
2. Langhals, H.; Demmig, S.; Huber, H. Rotational barriers in perylene fluorescent dyes, Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy 1988, 44A, 1189-1193.
3. Langhals, H. Lightfast, readily soluble perylenetetracarboxylic (bis)imide fluorescent dyes, Ger. Offen. 1988, DE 3703495 A1 19880818.
4. Langhals, H. (Polymeric) perylenetetracarboxylic diimide dyes having high dielectric constants, Ger. Offen. 1989, DE 3814647 A1 19891005.
5. Langhals, H.; Potrawa, T. Optical memory devices containing color changeable dyes, and dyes therefor, PCT Int. Appl. 1990, WO 9001480 A1 19900222.
6. Langhals, H.; Demmig, S. Perylene dyes and their use as permanent toner in electrophotography and laser printing, Ger. Offen. 1991, DE 4007618 A1 19910912.
7. Schott, H.; Von Cunow, D.; Langhals, H. Labeling of liposomes with intercalating perylene fluorescent dyes, Biochim. Biophys. Acta, Biomembranes 1992, 1110, 151-157.
8. Langhals, H.; Jona, W. The identification of carbonyl compounds by fluorescence: a novel carbonyl-derivatizing reagent, Chemistry - A European Journal 1998, 4, 2110-2116.
9. Langhals, H.; Kirner, S. Novel fluorescent dyes by the extension of the core of perylenetetracarboxylic bisimides, Europ. J. Org. Chem. 2000, 365-380.
10. Langhals, H.; Kirner, S.; Blanke, P.; Speckbacher, M. Core-extended perylene bisimide colorants, their production and their use, PCT Int. Appl. 2000, WO 2000023446 A1 20000427.
11. Speckbacher, M.; Baumeister, J. Use of fluorescent perylene compounds for the treatment of human hair, PCT Int. Appl. 2005, WO 2005123012 A1 20051229.
12. Singh, Th. B.; Erten, S.; Guenes, S.; Zafer, C.; Turkmen, G.; Kuban, B.; Teoman, Y.; Sariciftci, N. S.; Icli, S. Soluble derivatives of perylene and naphthalene diimide for n-channel organic field-effect transistors, Organic Electronics 2006, 7, 480-489.
13. Langhals, H. Perylene and indigo dyes as fluorescent nanoparticles in aqueous phase, Ger. Offen. 2007, DE 102006020190 A1 20071108.
14. Langhals, H. Brightly shining nanoparticles: Lipophilic perylene bisimides in aqueous phase, New Journal of Chemistry 2008, 32, 21-23.
15. Langhals, H.; Pust, T. Perylenetetracarboxylic diimide dye-containing micellar nanoparticles and applications, Ger. Offen. 2010, DE 102009008661 A1 20100819.
16. Langhals, H.; Pust, T. Lipophilic optical supramolecular nano devices in the aqueous phase, Green and Sustainable Chemistry 2011, 1, 1-6.
17. Boobalan, G.; Imran, P. M.; Nagarajan, S. Self-assembly, optical and electrical properties of fork-tailed perylene bisimides, Superlattices and Microstructures 2012, 51, 921-932.
18. Langhals, H.; Hofer, A. Using imidazoloterrylene bisimides for contactless temperature measurement in hard accessible areas, Ger. Offen. 2013, DE 102012008287 A1 20131017.
19. Savoie, B. M.; Kohlstedt, K. L.; Jackson, N. E.; Chen, Lin X.; de la Cruz, M. O.; Schatz, G. C.; Marks, T. J.; Ratner, M. A. Mesoscale molecular network formation in amorphous organic materials, Proceedings of the National Academy of Sciences of the United States of America 2014, 111, 10055-10060.
20. Madhurima, V.; Priyanka, K. Greeshma; Pavan, K. S. N. D.; Nagarajan, S. Analysis of wetting of perylene diimide thin films-on-glass by water, Key Engineering Materials 2014, 594-595(Advanced Materials Engineering and Technology II, 1074-1077.
21. Boobalan, G.; Imran, P. K. M.; Manoharan, C.; Nagarajan, S. Optical and electrical properties of new perylene diimide thin films, J. Electronic Materials 2015, 44, 4000-4005.
22. Gao, Deqing; Chen, Naiwu; Zhu, Jie; Zheng, Chaoyue; Wu, Huarui; Huang, Wei Preparing method of electron/hole double-channel polymer material, and application thereof in organic solar cell, Faming Zhuanli Shenqing 2016, CN 105669953 A 20160615.
23. Fu, Huiting; Meng, Dong; Meng, Xiangyi; Sun, Xiaobo; Huo, Lijun; Fan, Yuzun; Li, Yan; Ma, Wei; Sun, Yanming; Wang, Zhaohui Influence of alkyl chains on photovoltaic properties of 3D rylene propeller electron acceptors, J. Materials Chemistry A: Materials for Energy and Sustainability 2017, 5, 3475-3482.
24. Chen, Naiwu; Lu, Jurong; Wang, Danbei; Zheng, Chaoyue; Wu, Huarui; Zhang, Hongmei; Gao, Deqing A double-cable poly(fluorene-alt-thiophene) with bay-substituted perylenediimide pendants: An efficient interfacial material in bulk-heterojunction solar cells, Macromolecules (Washington, DC, United States) 2018, 51, 80-90.