15. Nishimura H, Tanaka K, Morisaki Y, Chujo Y, Wakamiya A, Murata Y (2017) Oxygen-bridged
diphenylnaphthylamine as a scaffold for full-color circularly polarized luminescent materials.
J Org Chem 82:5242–5249
16. Liu Y, Cerezo J, Mazzeo G, Lin N, Zhao X, Longhi G, Abbate S, Santoro F (2016) Vibronic
coupling explains the different shape of electronic circular dichroism and of circularly polarized
luminescence spectra of hexahelicenes. J Chem Theory Comput 12:2799–2819
17. 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 136:5555–5558
18. Tanaka M, Shibata Y, Nakamura K, Teraoka K, Uekusa H, Nakazono K, Takata T, Tanaka K
(2016) Gold-catalyzed enantioselective synthesis, crystal structure, and photophysical/
chiroptical properties of aza[10]helicenes. Chem Eur J 22:9537–9541
19. Otani T, Tsuyuki A, Iwachi T, Someya S, Tateno K, Kawai H, Saito T, Kanyiva KS, Shibata T
(2017) Facile two-step synthesis of 1,10-phenanthroline-derived polyaza[7]helicenes with high
fluorescence and CPL efficiency. Angew Chem Int Ed 56:3906–3910
20. Abbate S, Longhi G, Lebon F, Castiglioni E, Superchi S, Pisani L, Fontana F, Torricelli F,
Caronna T, Villani C, Sabia R, Tommasini M, Lucotti A, Mendola D, Mele A, Lightner DA
(2014) Helical sense-responsive and substituent-sensitive features in vibrational and electronic
circular dichroism, in circularly polarized luminescence, and in Raman spectra of some simple
optically active hexahelicenes. J Phys Chem C 118:1682–1695
21. 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 smallmolecule dopant. Adv Mater 25:2624–2628
22. Nakai Y, Mori T, Sato K, Inoue Y (2013) Theoretical and experimental studies of circular
dichroism of mono and diazonia[6]helicenes. J Phys Chem A 117:5082–5092
23. Tanaka H, Ikenosako M, Kato Y, Fujiki M, Inoue Y, Mori T (2018) Symmetry-based rational
design for boosting chiroptical responses. Commun Chem 1:38
24. 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 51:10333–10336
25. Ushiyama A, Hiroto S, Yuasa J, Kawai T, Shinokubo H (2017) Synthesis of a figure-eight
azahelicene dimer with high emission and CPL properties. Org Chem Front 4:664–667
26. Sakai H, Kubota T, Yuasa J, Araki Y, Sakanoue T, Takenobu T, Wada T, Kawai T, Hasobe T
(2016) Synthetic control of photophysical process and circularly polarized luminescence of
[5]carbohelicene derivatives substituted by maleimide units. J Phys Chem C 120:7860–7869
27. Sakai H, Kubota T, Yuasa J, Araki Y, Sakanoue T, Takenobu T, Wada T, Kawai T, Hasobe T
(2016) Protonation-induced red-coloured circularly polarized luminescence of [5]carbohelicene
fused by benzimidazole. Org Biomol Chem 14:6738–6743
28. Li M, Lu H-Y, Zhang C, Shi L, Tang Z, Chen C-F (2016) Helical aromatic imide based
enantiomers with full color circularly polarized luminescence. Chem Commun 52:9921–9924
29. Delgado IH, Pascal S, Wallabregue A, Duwald R, Besnard C, Guenee L, Nancoz C, Vauthey E,
Tovar RC, Lunkley JL, Muller G, Lacour J (2016) Functionalized cationic [4]helicenes with
unique tuning of absorption, fluorescence and chiroptical properties up to the far-red range.
Chem Sci 7:4685–4693
30. Pascal S, Besnard C, Zinna F, Di Bari L, Le Guennic B, Jacquemin D, Lacour J (2016)
Zwitterionic [4]helicene: a water-soluble and reversible PH-triggered ECD/CPL chiroptical
switch in the UV and red spectral regions. Org Biomol Chem 14:4590–4594
31. Bosson J, Labrador GM, Pascal S, Miannay FA, Yushchenko O, Li H, Bouffier L, Sojic N,
Tovar RC, Muller G, Jacquemin D, Laurent AD, Le Guennic B, Vauthey E, Lacour J (2016)
Physicochemical and electronic properties of cationic [6]helicenes: from chemical and
electrochemical stabilities to far-red (polarized) luminescence. Chem Eur J 22:18394–18403
32. Kaseyama T, Furumi S, Zhang X, Tanaka K, Takeuchi M (2011) Hierarchical assembly
of a phthalhydrazide-functionalized helicene. Angew Chem Int Ed 50:3684–3687
94
J. Crassous
diphenylnaphthylamine as a scaffold for full-color circularly polarized luminescent materials.
J Org Chem 82:5242–5249
16. Liu Y, Cerezo J, Mazzeo G, Lin N, Zhao X, Longhi G, Abbate S, Santoro F (2016) Vibronic
coupling explains the different shape of electronic circular dichroism and of circularly polarized
luminescence spectra of hexahelicenes. J Chem Theory Comput 12:2799–2819
17. 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 136:5555–5558
18. Tanaka M, Shibata Y, Nakamura K, Teraoka K, Uekusa H, Nakazono K, Takata T, Tanaka K
(2016) Gold-catalyzed enantioselective synthesis, crystal structure, and photophysical/
chiroptical properties of aza[10]helicenes. Chem Eur J 22:9537–9541
19. Otani T, Tsuyuki A, Iwachi T, Someya S, Tateno K, Kawai H, Saito T, Kanyiva KS, Shibata T
(2017) Facile two-step synthesis of 1,10-phenanthroline-derived polyaza[7]helicenes with high
fluorescence and CPL efficiency. Angew Chem Int Ed 56:3906–3910
20. Abbate S, Longhi G, Lebon F, Castiglioni E, Superchi S, Pisani L, Fontana F, Torricelli F,
Caronna T, Villani C, Sabia R, Tommasini M, Lucotti A, Mendola D, Mele A, Lightner DA
(2014) Helical sense-responsive and substituent-sensitive features in vibrational and electronic
circular dichroism, in circularly polarized luminescence, and in Raman spectra of some simple
optically active hexahelicenes. J Phys Chem C 118:1682–1695
21. 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 smallmolecule dopant. Adv Mater 25:2624–2628
22. Nakai Y, Mori T, Sato K, Inoue Y (2013) Theoretical and experimental studies of circular
dichroism of mono and diazonia[6]helicenes. J Phys Chem A 117:5082–5092
23. Tanaka H, Ikenosako M, Kato Y, Fujiki M, Inoue Y, Mori T (2018) Symmetry-based rational
design for boosting chiroptical responses. Commun Chem 1:38
24. 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 51:10333–10336
25. Ushiyama A, Hiroto S, Yuasa J, Kawai T, Shinokubo H (2017) Synthesis of a figure-eight
azahelicene dimer with high emission and CPL properties. Org Chem Front 4:664–667
26. Sakai H, Kubota T, Yuasa J, Araki Y, Sakanoue T, Takenobu T, Wada T, Kawai T, Hasobe T
(2016) Synthetic control of photophysical process and circularly polarized luminescence of
[5]carbohelicene derivatives substituted by maleimide units. J Phys Chem C 120:7860–7869
27. Sakai H, Kubota T, Yuasa J, Araki Y, Sakanoue T, Takenobu T, Wada T, Kawai T, Hasobe T
(2016) Protonation-induced red-coloured circularly polarized luminescence of [5]carbohelicene
fused by benzimidazole. Org Biomol Chem 14:6738–6743
28. Li M, Lu H-Y, Zhang C, Shi L, Tang Z, Chen C-F (2016) Helical aromatic imide based
enantiomers with full color circularly polarized luminescence. Chem Commun 52:9921–9924
29. Delgado IH, Pascal S, Wallabregue A, Duwald R, Besnard C, Guenee L, Nancoz C, Vauthey E,
Tovar RC, Lunkley JL, Muller G, Lacour J (2016) Functionalized cationic [4]helicenes with
unique tuning of absorption, fluorescence and chiroptical properties up to the far-red range.
Chem Sci 7:4685–4693
30. Pascal S, Besnard C, Zinna F, Di Bari L, Le Guennic B, Jacquemin D, Lacour J (2016)
Zwitterionic [4]helicene: a water-soluble and reversible PH-triggered ECD/CPL chiroptical
switch in the UV and red spectral regions. Org Biomol Chem 14:4590–4594
31. Bosson J, Labrador GM, Pascal S, Miannay FA, Yushchenko O, Li H, Bouffier L, Sojic N,
Tovar RC, Muller G, Jacquemin D, Laurent AD, Le Guennic B, Vauthey E, Lacour J (2016)
Physicochemical and electronic properties of cationic [6]helicenes: from chemical and
electrochemical stabilities to far-red (polarized) luminescence. Chem Eur J 22:18394–18403
32. Kaseyama T, Furumi S, Zhang X, Tanaka K, Takeuchi M (2011) Hierarchical assembly
of a phthalhydrazide-functionalized helicene. Angew Chem Int Ed 50:3684–3687
94
J. Crassous