Abstract
Circularly polarized luminescence (CPL) represents the differential emission of left- and right-handed circularly polarized light, which gives information of the excited states of the chiral systems. Because of the combination of specific helical chirality and polycyclic aromatic hydrocarbons (PAH), most helicenes show CPL properties. And supramolecular structures self-assembled by helicenes give relatively higher g lum values than single helicenes. Due to the good thermal and chemical stability, strong intensity and good quantum yields of fluorescence or phosphorescence, helicenes with π-conjugated skeletons are also good candidates for organic electronics. Especially, it was found that helicenes, aza[6]helicene and boron-embedded [4]helicenes can be used as emitting materials in organic light emitting diodes, while thiahelicenes, azaborahelicene, and highly contorted PAH bearing four [4]helicene and two [5]helicene units can be applied in organic field-effect transistor devices. In addition, some helicenes are also utilized in the organic photovoltaic devices, optical waveguides, and organic spintronic devices.
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References
Kumar J, Nakashima T, Kawai T (2015) Circularly polarized luminescence in chiral molecules and supramolecular assemblies. J Phys Chem Lett 6(17):3445–3452
Sánchez-Carnerero EM, Agarrabeitia AR, Moreno F, Maroto BL, Muller G, Ortiz MJ, de la Moya S (2015) Circularly polarized luminescence from simple organic molecules. Chem Eur J 21(39):13488–13500
Lunkley JL, Shirotani D, Yamanari K, Kaizaki S, Muller G (2008) Extraordinary circularly polarized luminescence activity exhibited by cesium Tetrakis(3-heptafluoro-butylryl-(+)-camphorato) Eu(III) complexes in EtOH and CHCl3 Solutions. J Am Chem Soc 130(42):13814–13815
Phillips KES, Katz TJ, Jockusch S, Lovinger AJ, Turro NJ (2001) Synthesis and properties of an aggregating heterocyclic helicene. J Am Chem Soc 123(48):11899–11907
Kaseyama T, Furumi S, Zhang X, Tanaka K, Takeuchi M (2011) Hierarchical assembly of a phthalhydrazide-functionalized helicene. Angew Chem Int Ed 50(16):3684–3687
Field JE, Muller G, Riehl JP, Venkataraman D (2003) Circularly polarized luminescence from bridged triarylamine helicenes. J Am Chem Soc 125(39):11808–11809
Goto K, Yamaguchi R, Hiroto S, Ueno H, Kawai T, Shinokubo H (2012) Intermolecular oxidative annulation of 2-Aminoanthracenes to Diazaacenes and Aza[7]helicenes. Angew Chem Int Ed 51(41):10333–10336
Matsuno T, Koyama Y, Hiroto S, Kumar J, Kawai T, Shinokubo H (2015) Isolation of a 1,4-diketone intermediate in oxidative dimerization of 2-hydroxyanthracene and its conversion to oxahelicene. Chem Commun (Camb) 51(22):4607–4610
Sawada Y, Furumi S, Takai A, Takeuchi M, Noguchi K, Tanaka K (2012) Rhodium-Catalyzed enantioselective synthesis, crystal structures, and photophysical properties of helically chiral 1,1′-Bitriphenylenes. J Am Chem Soc 134(9):4080–4083
Oyama H, Nakano K, Harada T, Kuroda R, Naito M, Nobusawa K, Nozaki K (2013) Facile synthetic route to highly luminescent Sila[7]helicene. Org Lett 15(9):2104–2107
Murayama K, Oike Y, Furumi S, Takeuchi M, Noguchi K, Tanaka K (2015) Enantioselective synthesis, crystal structure, and photophysical properties of a 1,1′-Bitriphenylene-Based Sila[7]helicene. Eur J Org Chem 7:1409–1414
Nakamura K, Furumi S, Takeuchi M, Shibuya T, Tanaka K (2014) Enantioselective synthesis and enhanced circularly polarized luminescence of S-Shaped double azahelicenes. J Am Chem Soc 136(15):5555–5558
Shen C, Anger E, Srebro M, Vanthuyne N, Deol KK, Jefferson TD, Muller G, Williams JAG, Toupet L, Roussel C, Autschbach J, Reau R, Crassous J (2014) Straightforward access to mono- and bis-cycloplatinated helicenes displaying circularly polarized phosphorescence by using crystallization resolution methods. Chem Sci 5(5):1915–1927
Saleh N, Moore B, Srebro M, Vanthuyne N, Toupet L, Williams JAG, Roussel C, Deol KK, Muller G, Autschbach J, Crassous J (2015) Acid/Base-Triggered switching of circularly polarized luminescence and electronic circular dichroism in organic and organometallic helicenes. Chem Eur J 21(4):1673–1681
Saleh N, Srebro M, Reynaldo T, Vanthuyne N, Toupet L, Chang VY, Muller G, Williams JAG, Roussel C, Autschbach J, Crassous J (2015) Enantio-enriched CPL-active helicene-bipyridine-rhenium complexes. Chem Commun (Camb) 51(18):3754–3757
Sahasithiwat S, Mophuang T, Menbangpung L, Kamtonwong S, Sooksimuang T (2010) 3,12-Dimethoxy-7,8-dicyano-[5]helicene as a novel emissive material for organic light-emitting diode. Synth Met 160(11–12):1148–1152
Shi L, Liu Z, Dong G, Duan L, Qiu Y, Jia J, Guo W, Zhao D, Cui D, Tao X (2012) Synthesis, structure, properties, and application of a carbazole-based Diaza[7]helicene in a deep-blue-emitting OLED. Chem Eur J 18(26):8092–8099
Hua W, Liu Z, Duan L, Dong G, Qiu Y, Zhang B, Cui D, Tao X, Cheng N, Liu Y (2015) Deep-blue electroluminescence from nondoped and doped organic light-emitting diodes (OLEDs) based on a new monoaza[6]helicene. RSC Adv 5(1):75–84
Hirai H, Nakajima K, Nakatsuka S, Shiren K, Ni J, Nomura S, Ikuta T, Hatakeyama T (2015) One-step borylation of 1,3-Diaryloxybenzenes towards efficient materials for organic light-emitting diodes. Angew Chem Int Ed 54(46):13581–13585
Yang Y, da Costa RC, Smilgies D-M, Campbell AJ, Fuchter MJ (2013) Induction of circularly polarized electroluminescence from an achiral light-emitting polymer via a chiral small-molecule dopant. Adv Mater 25(18):2624–2628
Kim C, Marks TJ, Facchetti A, Schiavo M, Bossi A, Maiorana S, Licandro E, Todescato F, Toffanin S, Muccini M, Graiff C, Tiripicchio A (2009) Synthesis, characterization, and transistor response of tetrathia-[7]-helicene precursors and derivatives. Org Electron 10(8):1511–1520
Hatakeyama T, Hashimoto S, Oba T, Nakamura M (2012) Azaboradibenzo[6]helicene: carrier inversion induced by helical homochirality. J Am Chem Soc 134(48):19600–19603
Si Y, Yang G (2013) Photophysical properties of azaboradibenzo[6]helicene derivatives. J Mater Chem C 1:2354–2361
Xiao S, Kang SJ, Wu Y, Ahn S, Kim JB, Loo Y, Siegrist T, Steigerwald ML, Li H, Nuckolls C (2013) Supersized contorted aromatics. Chem Sci 4(5):2018–2023
Yang Y, da Costa RC, Fuchter MJ, Campbell AJ (2013) Circularly polarized light detection by a chiral organic semiconductor transistor. Nat Photon 7(8):634–638
Liu X, Wang Y, Gao J, Jiang L, Qi X, Hao W, Zou S, Zhang H, Li H, Hu W (2014) Easily solution-processed, high-performance microribbon transistors based on a 2D condensed benzothiophene derivative. Chem Commun (Camb) 50(4):442–444
Li M, Yao W, Chen J-D, Lu H-Y, Zhao Y, Chen C-F (2014) Tetrahydro[5]helicene-based full-color emission dyes in both solution and solid states: synthesis, structures, photophysical properties and optical waveguide applications. J Mater Chem C 2(39):8373–8380
Li X-J, Li M, Yao W, Lu H-Y, Zhao Y, Chen C-F (2015) Dialkoxybenzo[j]fluoranthenes: synthesis, structures, photophysical properties, and optical waveguide application. RSC Adv 5(24):18609–18614
Kiran V, Mathew SP, Cohen SR, Hernández Delgado I, Lacour J, Naaman R (2016) Helicenes—a new class of organic spin filter. Adv Mater 28(10):1957–1962
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Chen, CF., Shen, Y. (2017). Circularly Polarized Luminescence and Organic Electronics. In: Helicene Chemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-53168-6_12
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DOI: https://doi.org/10.1007/978-3-662-53168-6_12
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