33. Yamano R, Hara J, Murayama K, Sugiyama H, Teraoka K, Uekusa H, Kawauchi S, Shibata Y,
Tanaka K (2017) Rh-mediated enantioselective synthesis, crystal structures, and photophysical/
chiroptical properties of phenanthrenol-based[9]helicene-like molecules. Org Lett 19:42–45
34. 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 51:4607–4610
35. Gupta R, Cabreros TA, Muller G, Bedekar AV (2018) Enantiomerically pure 5,13-dicyano-9oxa[7]helicene: synthesis and study. Eur J Org Chem 2018:5397–5405
36. Sundar MS, Talele HR, Mande HM, Bedekar AV, Tovar RC, Muller G (2014) Synthesis
of enantiomerically pure helicene like bis-oxazines from atropisomeric 7,7
0 -dihydroxy
BINOL: preliminary measurements of the circularly polarized luminescence. Tetrahedron Lett
55:1760–1764
37. Phillips KES, Katz TJ, Jockusch S, Lovinger AJ, Turro NJ (2001) Synthesis and properties
of an aggregating heterocyclic helicene. J Am Chem Soc 123:11899–11907
38. Riehl JP, Richardson FS (1986) Circularly polarized luminescence spectroscopy. Chem Rev
86:1–16
39. Yamamoto Y, Sakai H, Yuasa J, Araki Y, Wada T, Sakanoue T, Takenobu T, Kawai T,
Hasobe T (2016) Controlled excited-state dynamics and enhanced fluorescence property of
tetrasulfone[9]helicene by a simple synthetic process. J Phys Chem C 120:7421–7427
40. Yamamoto Y, Sakai H, Yuasa J, Araki Y, Wada T, Sakanoue T, Takenobu T, Kawai T,
Hasobe T (2016) Synthetic control of the excited-state dynamics and circularly polarized
luminescence of fluorescent “push–pull” tetrathia[9]helicenes. Chem Eur J 22:4263–4273
41. Biet T, Cauchy T, Sun Q, Ding J, Hauser A, Oulevey P, Bürgi T, Jacquemin D, Vanthuyne N,
Crassous J, Avarvari N (2017) Triplet state CPL active helicene–dithiolene platinum bipyridine
complexes. Chem Commun 53:9210–9213
42. Shen C, Srebro-Hooper M, Jean M, Vanthuyne N, Toupet L, Williams JAG, Torres AR,
Riives AJ, Muller G, Autschbach J, Crassous J (2017) Synthesis and chiroptical properties of
hexa-, octa-, and decaazaborahelicenes: influence of helicene size and of the number of boron
atoms. Chem Eur J 23:407–418
43. Dominguez Z, Lopez-Rodriguez R, Alvarez E, Abbate S, Longhi G, Pischel U, Ros A (2018)
Azabora[5]helicene charge-transfer dyes show efficient and spectrally variable circularly
polarized luminescence. Chem Eur J 24:12660–12668
44. Katayama T, Nakatsuka S, Hirai H, Yasuda N, Kumar J, Kawai T, Hatakeyama T (2016)
Two-step synthesis of boron-fused double helicenes. J Am Chem Soc 138:5210–5213
45. Miyamoto F, Nakatsuka S, Yamada K, Nakayama K, Hatakeyama T (2015) Synthesis of
boron-doped polycyclic aromatic hydrocarbons by tandem intramolecular electrophilic
arene borylation. Org Lett 17:6158–6161
46. Hatakeyama T, Shiren K, Nakajima K, Nomura S, Nakatsuka S, Kinoshita K, Ni J, Ono Y,
Ikuta T (2016) Ultrapure blue thermally activated delayed fluorescence molecules: efficient
HOMO-LUMO separation by the multiple resonance effect. Adv Mater 28:2777–2781
47. 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 15:2104–2107
48. Murayama K, Oike Y, Furumi S, Takeuchi M, Noguchi K, Tanaka K (2015) Enantioselective
synthesis, crystal structure, and photophysical properties of a 1,1
0 -bitriphenylene-based sila[7]
helicene. Eur J Org Chem 2015:1409–1414
49. Hellou N, Srebro-Hooper M, Favereau L, Zinna F, Caytan E, Toupet L, Dorcet V, Jean M,
Vanthuyne N, Williams JAG, Di Bari L, Autschbach J, Crassous J (2017) Enantiopure
cycloiridiated complexes bearing a pentahelicenic N-heterocyclic carbene and displaying
long-lived circularly-polarized phosphorescence. Angew Chem Int Ed 56:8236–8239
50. Duffy MP, Delaunay W, Bouit P-A, Hissler M (2016) π-Conjugated phospholes and
their incorporation into devices: components with a great deal of potential. Chem Soc Rev
45:5296–5310
4 Circularly Polarized Luminescence in Helicene and Helicenoid Derivatives
95
Tanaka K (2017) Rh-mediated enantioselective synthesis, crystal structures, and photophysical/
chiroptical properties of phenanthrenol-based[9]helicene-like molecules. Org Lett 19:42–45
34. 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 51:4607–4610
35. Gupta R, Cabreros TA, Muller G, Bedekar AV (2018) Enantiomerically pure 5,13-dicyano-9oxa[7]helicene: synthesis and study. Eur J Org Chem 2018:5397–5405
36. Sundar MS, Talele HR, Mande HM, Bedekar AV, Tovar RC, Muller G (2014) Synthesis
of enantiomerically pure helicene like bis-oxazines from atropisomeric 7,7
0 -dihydroxy
BINOL: preliminary measurements of the circularly polarized luminescence. Tetrahedron Lett
55:1760–1764
37. Phillips KES, Katz TJ, Jockusch S, Lovinger AJ, Turro NJ (2001) Synthesis and properties
of an aggregating heterocyclic helicene. J Am Chem Soc 123:11899–11907
38. Riehl JP, Richardson FS (1986) Circularly polarized luminescence spectroscopy. Chem Rev
86:1–16
39. Yamamoto Y, Sakai H, Yuasa J, Araki Y, Wada T, Sakanoue T, Takenobu T, Kawai T,
Hasobe T (2016) Controlled excited-state dynamics and enhanced fluorescence property of
tetrasulfone[9]helicene by a simple synthetic process. J Phys Chem C 120:7421–7427
40. Yamamoto Y, Sakai H, Yuasa J, Araki Y, Wada T, Sakanoue T, Takenobu T, Kawai T,
Hasobe T (2016) Synthetic control of the excited-state dynamics and circularly polarized
luminescence of fluorescent “push–pull” tetrathia[9]helicenes. Chem Eur J 22:4263–4273
41. Biet T, Cauchy T, Sun Q, Ding J, Hauser A, Oulevey P, Bürgi T, Jacquemin D, Vanthuyne N,
Crassous J, Avarvari N (2017) Triplet state CPL active helicene–dithiolene platinum bipyridine
complexes. Chem Commun 53:9210–9213
42. Shen C, Srebro-Hooper M, Jean M, Vanthuyne N, Toupet L, Williams JAG, Torres AR,
Riives AJ, Muller G, Autschbach J, Crassous J (2017) Synthesis and chiroptical properties of
hexa-, octa-, and decaazaborahelicenes: influence of helicene size and of the number of boron
atoms. Chem Eur J 23:407–418
43. Dominguez Z, Lopez-Rodriguez R, Alvarez E, Abbate S, Longhi G, Pischel U, Ros A (2018)
Azabora[5]helicene charge-transfer dyes show efficient and spectrally variable circularly
polarized luminescence. Chem Eur J 24:12660–12668
44. Katayama T, Nakatsuka S, Hirai H, Yasuda N, Kumar J, Kawai T, Hatakeyama T (2016)
Two-step synthesis of boron-fused double helicenes. J Am Chem Soc 138:5210–5213
45. Miyamoto F, Nakatsuka S, Yamada K, Nakayama K, Hatakeyama T (2015) Synthesis of
boron-doped polycyclic aromatic hydrocarbons by tandem intramolecular electrophilic
arene borylation. Org Lett 17:6158–6161
46. Hatakeyama T, Shiren K, Nakajima K, Nomura S, Nakatsuka S, Kinoshita K, Ni J, Ono Y,
Ikuta T (2016) Ultrapure blue thermally activated delayed fluorescence molecules: efficient
HOMO-LUMO separation by the multiple resonance effect. Adv Mater 28:2777–2781
47. 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 15:2104–2107
48. Murayama K, Oike Y, Furumi S, Takeuchi M, Noguchi K, Tanaka K (2015) Enantioselective
synthesis, crystal structure, and photophysical properties of a 1,1
0 -bitriphenylene-based sila[7]
helicene. Eur J Org Chem 2015:1409–1414
49. Hellou N, Srebro-Hooper M, Favereau L, Zinna F, Caytan E, Toupet L, Dorcet V, Jean M,
Vanthuyne N, Williams JAG, Di Bari L, Autschbach J, Crassous J (2017) Enantiopure
cycloiridiated complexes bearing a pentahelicenic N-heterocyclic carbene and displaying
long-lived circularly-polarized phosphorescence. Angew Chem Int Ed 56:8236–8239
50. Duffy MP, Delaunay W, Bouit P-A, Hissler M (2016) π-Conjugated phospholes and
their incorporation into devices: components with a great deal of potential. Chem Soc Rev
45:5296–5310
4 Circularly Polarized Luminescence in Helicene and Helicenoid Derivatives
95