S-17
  O=C(N(C(CCCCCCCC)CCCCCCCC)C7=O)C2=CC=C(C4=CC=C6C5=C(C(N(C(CCCCCCCC)CCCCCCCC)C6=O)=O)C=CC3=C45)C1=C3C=CC7=C12

N,N‘-Bis(1-octylnonyl)-3,4:9,10-perylenebis(dicarboximide); 2,9-bis-(1-octylnonyl)anthra[2,1,9-def;6,5,10-d‘e‘f‘]diisoquinoline-1,3,8,10(2H,9H)-tetraone; 2,9-bis-(9-heptadecyl)anthra[2,1,9-def;6,5,10-d‘e‘f‘]diisoquinoline-1,3,8,10(2H,9H)-tetraone, RN 139260-31-4:
M.p. 102-103°C, reddish brown rhombes, crystal transformation several degrees below melting point. UV (CHCl3): λmax (ε) = 458.5 nm (18710), 489.5 (51550), 526 (85650). C58H78N2O4 (867.3) calcd. C 80.33, H 9.06, N 3.23; found C 80.79, H 9.04, N 3.34.

References, RN 139260-31-4:

*1. Langhals, H.; Demmig, S.; Potrawa, T. ‘The relation between packing effects and solid state fluorescence of dyes’, J. Prakt. Chem. (Leipzig) 1991, 333, 733-748.

2. Langhals, H.; Demmig, S. ‘Perylene dyes and their use as permanent toner in electrophotography and laser printing’, Ger. Offen. 1991, DE 4007618 A1 19910912; Chem. Abstr. 1992, 116, 117172.

3. Schott, H.; Von Cunow, D.; Langhals, H. ‘Labeling of liposomes with intercalating perylene fluorescent dyes’, Biochim. Biophys. Acta, Biomembranes 1992, 1110, 151-157.

4. Feiler, L.; Langhals, H.; Polborn, K. ‘Synthesis of perylene-3,4-dicarboximides - novel highly photostable fluorescent dyes’, Liebigs Ann. 1995, 1229-1244.

5. Langhals, H. ‘Preparation of high-purity perylene-3,4,9,10-tetracarboxylic acid 3,4-anhydride 9,10-imides’, Ger. Offen. 1995, DE 4421347 A1 19951221; Chem. Abstr. 1996, 124, 263384.

6. Langhals, H. ‘Perylene amidine imide dyes, their preparation and their use’, Ger. Offen. 1995, DE 4327273 A1 19950216; Chem. Abstr. 1995, 123, 58801.

7. Langhals, H.; Sprenger, S.; Brandherm, M.-T. ‘Perylenamidine-imide dyes’, Liebigs Annalen 1995, 481-486.

8. Langhals, H.; Feiler, L. ‘Lightfast fluorescent perylene-3,4-dicarboximide dyes, their preparation and their use’, Ger. Offen. 1995, DE 4338784 A1 19950518; Chem. Abstr. 1995, 123, 202037.

9. Langhals, H.; Jona, W. ‘The identification of carbonyl compounds by fluorescence: a novel carbonyl-derivatizing reagent’, Chem. Europ. J. 1998, 4, 2110-2116.

10. Langhals, H.; Blanke, P. ‘An approach to novel NIR dyes utilizing α-effect donor groups’, Dyes Pigm. 2003, 59, 109-116.

11. Speckbacher, M.; Baumeister, J, ‘Use of fluorescent perylene compounds for the treatment of human hair’, PCT Int. Appl. 2005, WO 2005123012 A1 20051229; Chem. Abstr. 2005, 144, 93800.

12. Biberdorf, J. D.; Holliday, B. J. ‘Novel perylene diimide containing polymer as an n-type material for polymer based electronic devices’, Polymer Preprints (American Chemical Society, Division of Polymer Chemistry) 2008, 49, 772-773; Chem. Abstr. 2008, 150, 474553.

13. Kim, Myung Hee; Cho, Min Ju; Kim, Kyung Hwan; Hoang, Mai Ha; Lee, Tae Wan; Jin, Jung-Il; Kang, Nam Su; Yu, Jae-Woong; Choi, Dong Hoon ‘Organic donor-σ-acceptor molecules based on 1,2,4,5-tetrakis((E)-2-(5‘-hexyl-2,2‘-bithiophen-5-yl)vinyl)benzene and perylene diimide derivative and their application to photovoltaic devices’, Organic Electronics 2009, 10, 1429-1441.

14. Holliday, B. J. ‘Polymerizable semiconductors, polymers thereof, and methods of making and using same’, U.S. Pat. Appl. Publ. 2010, US 20100038599 A1 20100218; Chem. Abstr. 2010, 152288074.

15. Langhals, H.; Pust, T. ‘Perylenetetracarboxylic diimide dye-containing micellar nanoparticles and applications’, Ger. Offen. 2010, DE 102009008661 A1 20100819; Chem. Abstr. 2010, 153, 336212.

16. Hasegawa, M. ‘Organic semiconductor material containing perylenetetracarboxylic acid diimide compound, and organic semiconductor element’, PCT Int. Appl. 2011, WO 2011105152 A1 20110901; Chem. Abstr. 2011, 155, 369418.

17. Langhals, H.; Pust, T. ‘Lipophilic optical supramolecular nano devices in the aqueous phase’, Green and Sustainable Chem 2011, 1, 1-6.

18. Supur, M.; Yamada, Y.; El-Khouly, M. E.; Honda, T.; Fukuzumi, S. ‘Electron delocalization in one-Dimensional perylenediimide nanobelts through photoinduced electron transfer’, J. Phys. Chem. C 2011, 115, 15040-15047.

19. Pho, T. V.; Toma, F. M.; Chabinyc, M. L.; Wudl, F. ‘Self-assembling decacyclene triimides prepared through a regioselective hextuple Friedel-Crafts carbamylation’, Angew. Chem., Int. Ed. 2013, 52, 1446-1451.

20. Glaz, M. S.; Biberdorf, J. D.; Nguyen, M. T.; Travis, J. J.; Holliday, B. J.; Vanden Bout, D. A. ‘Perylene diimide functionalized polynorbornene: A macromolecular scaffold for supramolecular self-assembly’, J. Materials Chem. C: Materials for Optical and Electronic Devices 2013, 1, 8060-8065.

21. 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.

22. Toma, F. M.; Puntoriero, F.; Pho, T. V.; La Rosa, M.; Jun, Y.-S.; Tremolet de Villers, B. J.; Pavlovich, J.; Stucky, G. D.; Campagna, S.; Wudl, F. ‘Polyimide dendrimers containing multiple electron donor-acceptor units and their unique photophysical properties’, Angew. Chem., Int. Ed. 2015, 54, 6775-6779.

23. Guo, Yikun; Li, Yunke; Awartani, Omar; Han, Han; Zhao, Jingbo; Ade, Harald; Yan, He; Zhao, Dahui ‘Improved performance of all-polymer solar cells enabled by naphthodiperylenetetraimide-based polymer acceptor’, Adv. Materials (Weinheim, Germany) 2017, 29, DOI:10.1002/adma.201700309.

back