S-19
N,N‘-Bis(1-nonyldecyl)-3,4:9,10-perylenebis(dicarboximide);
2,9-bis-(1-nonyldecyl)anthra[2,1,9-def;6,5,10-d‘e‘f‘]diisoquinoline-1,3,8,10(2H,9H)-tetraone; 2,9-bis-(10-nonadecyl)anthra[2,1,9-def;6,5,10-d‘e‘f‘]diisoquinoline-1,3,8,10(2H,9H)-tetraone, RN 130296-48-9:
M.p. 97°C, red crystals. UV (CHCl3): λmax
(ε) = 457.5 nm (19910), 488.5 (52720), 524.5 (87080). C62H86N2O4 (922.7) calcd. C 80.65, H 9.39, N 3.03; found C 80.51, H 9.61, N 3.15.
References, RN 130296-48-9:
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. Kaiser, H.; Lindner, J.; Langhals, H. ‘Synthesis of nonsymmetrically substituted perylene fluorescent dyes’, Chem. Ber. 1991, 124, 529-535.
3. 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.
4. Langhals, H.; Kaiser, H. ‘Asymmetric perylene fluorescent dyes and pigments, their preparation and use’, Ger. Offen. 1991, DE 4018830 A1 19911219.
5. Schott, H.; Von Cunow, D.; Langhals, H. ‘Labeling of liposomes with intercalating perylene fluorescent dyes’, Biochim. Biophys. Acta, Biomembranes 1992, 1110, 151-157.
6. 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.
7. Langhals, H. ‘Perylene amidine imide dyes, their preparation and their use’, Ger. Offen. 1995, DE 4327273 A1 19950216.
8. Langhals, H.; Sprenger, S.; Brandherm, M.-T. ‘Perylenamidine-imide dyes’, Liebigs Annalen 1995, 481-486.
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. Liu, R.; Holman, M. W.; Zang, L.; Adams, D. M. ‘Single-molecule spectroscopy of intramolecular electron transfer in donor-bridge-acceptor systems’, J. Phys. Chem. A 2003, 107, 6522-6526.
11. Langhals, H.; Blanke, P. ‘Perylenetetracarboxylic diimide fluorescent near-IR dyes, their production and their use’, Ger. Offen. 2003, DE 10132116 A1 20030130; Chem. Abstr. 2003, 138, 138778.
12. Wescott, L. D.; Mattern, D. ‘Lewis donor-σ-acceptor molecules incorporating a nonadecyl-swallowtailed perylenediimide acceptor’, J. Org. Chem. 2003, 68, 10058-10066.
13. Balakrishnan, K.; Datar, A.; Oitker, R.; Chen, H.; Zuo, J.; Zang, L. ‘Nanobelt self-assembly from an organic n-type semiconductor: Propoxyethyl-PTCDI’, J. Am. Chem. Soc. 2005, 127, 10496-10497.
14. Shin, Won Suk; Jeong, Hwan-Hee; Kim, Mi-Kyoung; Jin, Sung-Ho; Kim, Mi-Ra; Lee, Jin-Kook; Lee, Jae Wook; Gal, Yeong-Soon ‘Effects of functional groups at perylene diimide derivatives on organic photovoltaic device application’, J. Materials Chemistry 2006, 16, 384-390.
15. Balakrishnan, K.; Datar, A.; Naddo, T.; Huang, J.; Oitker, R.; Yen, M.; Zhao, J.; Zang, L. ‘Effect of side-chain substituents on self-assembly of perylene diimide molecules: Morphology control’, J. Am. Chem. Soc. 2006, 128, 7390-7398.
16. Do, Jung Yun; Kim, Bong Gun; Kwon, Ji yun; Shin, Won suk; Jin, Sung-Ho; Kim, Young-Inn ‘Soluble asymmetric perylene derivatives for organic solar cells’, Macromol. Symposia 2007, 249/250 (Advanced Polymers for Emerging Technologies, 461-465.
17. Shin, Won Suk; Jung, Hwan-Hee; Kim, Mi-Kyoung; Kim, Mi-Ra; Kim, Mi-Kyoung; Naidu, B. Vijaya Kumar; Jin, Sung-Ho; Lee, Jin-Kook; Lee, Jae Wook; Gal, Yeong-Soon ‘Photovoltaic properties of N-pyrrolidinyl substituted perylenebis(dicarboximide) derivatives’, Molecular Crystals and Liquid Crystals 2007, 462, 59-66.
18. Langhals, H. ‘Perylene and indigo dyes as fluorescent nanoparticles in aqueous phase’, Ger. Offen. 2007, DE 102006020190 A1 20071108; Chem. Abstr. 2007, 147, 503859.
19. Che, Yanke; Datar, Aniket; Yang, Xiaomei; Naddo, Tammene; Zhao, Jincai; Zang, Ling ‘Enhancing one-dimensional charge transport through intermolecular π-electron delocalization: Conductivity improvement for organic nanobelts’, J. Am. Chem. Soc. 2007, 129, 6354-6355.
20. Calzado, Eva M.; Villalvilla, J. M.; Boj, P. G.; Quintana, J. A.; Gomez, Rafael; Segura, J. L.; Diaz-Garcia, M. A.‘Effect of structural modifications in the spectral and laser properties of perylenediimide derivatives’, J. Phys. Chem. C 2007, 111, 13595-13605.
21. Kozma, E.; Kotowski, D.; Grieco, G.; Consonni, R.; Luzzati, S.; Catellani, M. ‘N-type molecules and polymers based on perylene bisimide and thiophene moieties for photovoltaic applications’, Materials Research Society Symposium Proceedings 2008, Volume Date2009, 1114E(Organic and Hybrid Materials for Large-Area Functional Systems, 1114-G08-15; Chem. Abstr. 2009, 151, 407383.
22. Zhang, Q.; Cirpan, A.; Russell, T. P.; Emrick, T. ‘Donor-acceptor poly(thiophene-block-perylene diimide) copolymers: Synthesis and solar cell fabrication’, Macromolecules (Washington, DC, United States) 2009, 42, 1079-1082.
23. Oh, S. H.; Kim, B. G.; Yun, S. J.; Maheswara, M.; Kim, K.; Do, J. Y. ‘The synthesis of symmetric and asymmetric perylene derivatives and their optical properties’, Dyes and Pigm. 2010, 85, 37-42.
24. Kozma, E.; Kotowski, D.; Bertini, F.; Luzzati, S.; Catellani, M. ‘Synthesis of donor-acceptor poly(perylene diimide-altoligothiophene) copolymers as n-type materials for polymeric solar cells’, Polymer 2010, 51, 2264-2270.
25. Kozma, E.; Munno, F.; Kotowski, D.; Bertini, F.; Luzzati, S.; Catellani, M. ‘Synthesis and characterization of perylene-based donor-acceptor copolymers containing triple bonds’, Synthetic Metals 2010, 160, 996-1001.
26. Langhals, H.; Pust, T. ‘Perylenetetracarboxylic diimide dye-containing micellar nanoparticles and applications’, Ger. Offen. 2010, DE 102009008661 A1 20100819; Chem. Abstr. 2010, 153, 336212.
27. Langhals, H.; Pust, T. ‘Lipophilic optical supramolecular nano devices in the aqueous phase’, Green and Sustainable Chemistry 2011, 1, 1-6.
28. Do, Jung Yun; Jang, Byungkwon ‘The efficient synthesis of N-fused coronene analogs and a related polyimide with near-infrared absorption’, Polymer Journal (Tokyo, Japan) 2013, 45, 1177-1182.
29. Jin, Sung-Ho; Ban, Taewon; Park, Juhyeon; Gal, Yeong-Soon; Lee, Jae Wook ‘Synthesis and photovoltaic properties of low-band gap copolymers containing perylene diimide derivatives’, Molecular Crystals and Liquid Crystals 2013, 578, 95-103.
30. Kozma, E.; Kotowski, D.; Catellani, M.; Luzzati, S.; Famulari, A.; Bertini, F. ‘Synthesis and characterization of new electron acceptor perylene diimide molecules for photovoltaic applications’, Dyes and Pigm. 2013, 99, 329-338.
31. Wang, Limin; Zhang, Liang; Wang, Guifeng; Wang, Feng; Chen, Lirong; Tian, He; Huang, Zhuo ‘Method for preparation of 1,7-dihydroxy-perylene-3,4:9,10-tetracarboxy diimine’, Faming Zhuanli Shenqing 2013, CN 102977099 A 20130320; Chem. Abstr. 2013, 158, 474716.
32. Kozma, E.; Kotowski, D.; Luzzati, S.; Catellani, M.; Bertini, F.; Famulari, A.; Raos, G. ‘Improving the efficiency of P3HT:perylene diimide solar cells via bay-substitution with fused aromatic rings’, RSC Advances 2013, 3, 9185-9188.
33. Choi, Mieon; Do, Jung Yun ‘Synthesis of perylene dianhydride-incorporated main chain polyimides and sequential structural transformation through a dipolar cycloaddition’, Reactive & Functional Polymers 2014, 84, 37-44.
34. Diehl, F. P.; Roos, C.; Duymaz, A.; Lunkenheimer, B.; Koehn, A.; Basche, T. ‘Emergence of coherence through variation of intermolecular distances in a series of molecular dimers’, J. Phys. Chem. Lett. 2014, 5, 262-269.
35. Fukumatsu, T.; Saeki, A.; Seki, S. ‘Modulation and evaluation of the charge carrier mobility in a polymer alloy of polythiophene and an insulating matrix with an electron accepting molecule’, Polymer Chemistry 2015, 6, 5860-5868.
36. Weintraub, M. T.; Xhakaj, E.; Austin, A.; Szarko, J. M. ‘The effects of donor : acceptor intermolecular mixing and acceptor crystallization on the composition ratio of blended, spin coated organic thin films’, J. Materials Chem. C: Materials for Optical and Electronic Devices 2016, 4, 7756-7765.