molecules that emit in the NIR region. We believe that our synthetic strategies
exemplified herein for enhanced chiroptical properties will provide a new perspective for future development of advanced luminescent materials.
References
1. Wu J, Pisula W, Müllen K (2007) Graphenes as potential material for electronics. Chem Rev
107(3):718–747
2. Hammer BAG, Müllen K (2016) Dimensional evolution of polyphenylenes: expanding in all
directions. Chem Rev 116(4):2103–2140
3. Ho R-M, Li M-C, Lin S-C, Wang H-F, Lee Y-D, Hasegawa H, Thomas EL (2012) Transfer of
chirality from molecule to phase in self-assembled chiral block copolymers. J Am Chem Soc
134(26):10974–10986
4. Watanabe K, Iida H, Akagi K (2012) Circularly polarized blue luminescent spherulites
consisting of hierarchically assembled ionic conjugated polymers with a helically π-stacked
structure. Adv Mater 24(48):6451–6456
5. Gingras M (2013) One hundred years of helicene chemistry. Part 3: applications and properties
of carbohelicenes. Chem Soc Rev 42(3):1051–1095
6. Gingras M (2013) One hundred years of helicene chemistry. Part 1: non-stereoselective
syntheses of carbohelicenes. Chem Soc Rev 42(3):968–1006
7. Verbiest T, Elshocht SV, Kauranen M, Hellemans L, Snauwaert J, Nuckolls C, Katz TJ,
Persoons A (1998) Strong enhancement of nonlinear optical properties through supramolecular
chirality. Science 282(5390):913–915
8. 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
9. Sakai H, Shinto S, Araki Y, Wada T, Sakanoue T, Takenobu T, Hasobe T (2014)
One-dimensional helical columnar formation and excimer-like excited-state of racemic
quinoxaline-fused [7]carbohelicenes in the crystal state. Chem Eur J 20(32):10099–10109
10. Reetz MT, Sostmann S (2001) 2,15-dihydroxy-hexahelicene (helixol): synthesis and use as an
enantioselective fluorescent sensor. Tetrahedron 57(13):2515–2520
11. 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
12. Shcherbina MÄ, Zeng X-B, Tadjiev T, Ungar G, Eichhorn SÄ, Phillips KÄÄ, Katz TÄ (2009)
Hollow six-stranded helical columns of a helicene. Angew Chem Int Ed 48(42):7837–7840
13. Verbiest T, Sioncke S, Persoons A, Vyklický L, Katz TJ (2002) Electric-field-modulated
circular-difference effects in second-harmonic generation from a chiral liquid crystal. Angew
Chem Int Ed 41(20):3882–3884
14. Nuckolls C, Shao R, Jang W-G, Clark NA, Walba DM, Katz TJ (2002) Electro-optic switching
by helicene liquid crystals. Chem Mater 14(2):773–776
15. Yuasa J, Ohno T, Tsumatori H, Shiba R, Kamikubo H, Kataoka M, Hasegawa Y, Kawai T
(2013) Fingerprint signatures of lanthanide circularly polarized luminescence from proteins
covalently labeled with a [small beta]-diketonate europium (iii) chelate. Chem Commun 49
(41):4604–4606
16. Riehl JP, Richardson FS (1986) Circularly polarized luminescence spectroscopy. Chem Rev 86
(1):1–16
17. Kumar J, Nakashima T, Tsumatori H, Kawai T (2014) Circularly polarized luminescence in
chiral aggregates: dependence of morphology on luminescence dissymmetry. J Phys Chem Lett
5(2):316–321
18. Kumar J, Nakashima T, Kawai T (2015) Circularly polarized luminescence in chiral molecules
and supramolecular assemblies. J Phys Chem Lett 6(17):3445–3452
5 Structural Control of Fluorescent Helicates for Improved Circularly Polarized. . .
113
exemplified herein for enhanced chiroptical properties will provide a new perspective for future development of advanced luminescent materials.
References
1. Wu J, Pisula W, Müllen K (2007) Graphenes as potential material for electronics. Chem Rev
107(3):718–747
2. Hammer BAG, Müllen K (2016) Dimensional evolution of polyphenylenes: expanding in all
directions. Chem Rev 116(4):2103–2140
3. Ho R-M, Li M-C, Lin S-C, Wang H-F, Lee Y-D, Hasegawa H, Thomas EL (2012) Transfer of
chirality from molecule to phase in self-assembled chiral block copolymers. J Am Chem Soc
134(26):10974–10986
4. Watanabe K, Iida H, Akagi K (2012) Circularly polarized blue luminescent spherulites
consisting of hierarchically assembled ionic conjugated polymers with a helically π-stacked
structure. Adv Mater 24(48):6451–6456
5. Gingras M (2013) One hundred years of helicene chemistry. Part 3: applications and properties
of carbohelicenes. Chem Soc Rev 42(3):1051–1095
6. Gingras M (2013) One hundred years of helicene chemistry. Part 1: non-stereoselective
syntheses of carbohelicenes. Chem Soc Rev 42(3):968–1006
7. Verbiest T, Elshocht SV, Kauranen M, Hellemans L, Snauwaert J, Nuckolls C, Katz TJ,
Persoons A (1998) Strong enhancement of nonlinear optical properties through supramolecular
chirality. Science 282(5390):913–915
8. 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
9. Sakai H, Shinto S, Araki Y, Wada T, Sakanoue T, Takenobu T, Hasobe T (2014)
One-dimensional helical columnar formation and excimer-like excited-state of racemic
quinoxaline-fused [7]carbohelicenes in the crystal state. Chem Eur J 20(32):10099–10109
10. Reetz MT, Sostmann S (2001) 2,15-dihydroxy-hexahelicene (helixol): synthesis and use as an
enantioselective fluorescent sensor. Tetrahedron 57(13):2515–2520
11. 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
12. Shcherbina MÄ, Zeng X-B, Tadjiev T, Ungar G, Eichhorn SÄ, Phillips KÄÄ, Katz TÄ (2009)
Hollow six-stranded helical columns of a helicene. Angew Chem Int Ed 48(42):7837–7840
13. Verbiest T, Sioncke S, Persoons A, Vyklický L, Katz TJ (2002) Electric-field-modulated
circular-difference effects in second-harmonic generation from a chiral liquid crystal. Angew
Chem Int Ed 41(20):3882–3884
14. Nuckolls C, Shao R, Jang W-G, Clark NA, Walba DM, Katz TJ (2002) Electro-optic switching
by helicene liquid crystals. Chem Mater 14(2):773–776
15. Yuasa J, Ohno T, Tsumatori H, Shiba R, Kamikubo H, Kataoka M, Hasegawa Y, Kawai T
(2013) Fingerprint signatures of lanthanide circularly polarized luminescence from proteins
covalently labeled with a [small beta]-diketonate europium (iii) chelate. Chem Commun 49
(41):4604–4606
16. Riehl JP, Richardson FS (1986) Circularly polarized luminescence spectroscopy. Chem Rev 86
(1):1–16
17. Kumar J, Nakashima T, Tsumatori H, Kawai T (2014) Circularly polarized luminescence in
chiral aggregates: dependence of morphology on luminescence dissymmetry. J Phys Chem Lett
5(2):316–321
18. Kumar J, Nakashima T, Kawai T (2015) Circularly polarized luminescence in chiral molecules
and supramolecular assemblies. J Phys Chem Lett 6(17):3445–3452
5 Structural Control of Fluorescent Helicates for Improved Circularly Polarized. . .
113