2.10 Conclusion
Axially chiral binaphthyl is one of the most significant fundamental sources of
chirality and fluorescence. An axially chiral binaphthyl fluorophore can emit circularly polarized luminescence (CPL) in the solution-dissolved state, PMMA filmdispersed state, and KBr pellet-dispersed state. The CPL emitted from an axially
chiral binaphthyl fluorophore can easily be tuned by (1) tuning the dihedral angle in
the binaphthyl unit, (2) employing the neighboring group effect that operates
between binaphthyl units, and (3) controlling its external environment, without the
need for the enantiomer. This chapter provides novel ideas for the design of novel
CPL materials in the solution and solid state.
References
1. Bian Z, He Y-B, Gao L-X (2003) Circular dichroism and circularly polarized
photoluminescence spectra of a new chiral conjugated polymers based on 1,1
0 -binaphthyl
structure. Gaodeng Xuexiao Huaxue Xuebao 24:559–561
2. 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'-dihydroxy BINOL:
preliminary measurements of the circularly polarized luminescence. Tetrahedron Lett
55:1760–1764
3. Park J, Yu T, Inagaki T, Akagi K (2015) Helical network polymers exhibiting circularly
polarized luminescence with thermal stability. Synthesis via photo-cross-link polymerizations
of methacrylate derivatives in a chiral nematic liquid crystal. Macromolecules 48:1930–1940
4. Ye Q, Zhu D, Xu L, Lu X, Lu Q (2016) The fabrication of helical fibers with circularly polarized
luminescence via ionic linkage of binaphthol and tetraphenylethylene derivatives. J Mater
Chem C 4:1497–1503
5. Uchida Y, Hirose T, Nakashima T, Kawai T, Matsuda K (2016) Synthesis and photophysical
properties of a 13,13
0 -bibenzo[b]perylenyl derivative as a π-extended 1,1
0 -binaphthyl analog.
Org Lett 18:2118–2121
6. Hirata S, Vacha M (2016) Circularly polarized persistent room-temperature phosphorescence
from metal-free chiral aromatics in air. J Phys Chem Lett 7:1539–1545
7. Shi L, Zhu L, Guo J, Zhang L, Shi Y, Zhang Y, Hou K, Zheng Y, Zhu Y, Lv J et al (2017) Selfassembly of chiral gold clusters into crystalline nanocubes of exceptional optical activity.
Angew Chem Int Ed 56:15397–15401
8. Shintani R, Misawa N, Takano R, Nozaki K (2017) Rhodium-catalyzed synthesis and optical
properties of silicon-bridged arylpyridines. Chem Eur J 23:2660–2665
9. Nishikawa H, Mochizuki D, Higuchi H, Okumura Y, Kikuchi H (2017) Reversible broadspectrum control of selective reflections of chiral nematic phases by closed-/open-type axially
chiral azo dopants. Chem Open 6:710–720
10. Koiso N, Kitagawa Y, Nakanishi T, Fushimi K, Hasegawa Y (2017) Eu(III) chiral coordination
polymer with a structural transformation system. Inorg Chem 56:5741–5747
11. Aoki R, Toyoda R, Kogel JF, Sakamoto R, Kumar J, Kitagawa Y, Harano K, Kawai T,
Nishihara H (2017) Bis(dipyrrinato)zinc(II) complex chiroptical wires: exfoliation into single
strands and intensification of circularly polarized luminescence. J Am Chem Soc
139:16024–16027
2 Circularly Polarized Luminescence of Axially Chiral Binaphthyl Fluorophores
29
Axially chiral binaphthyl is one of the most significant fundamental sources of
chirality and fluorescence. An axially chiral binaphthyl fluorophore can emit circularly polarized luminescence (CPL) in the solution-dissolved state, PMMA filmdispersed state, and KBr pellet-dispersed state. The CPL emitted from an axially
chiral binaphthyl fluorophore can easily be tuned by (1) tuning the dihedral angle in
the binaphthyl unit, (2) employing the neighboring group effect that operates
between binaphthyl units, and (3) controlling its external environment, without the
need for the enantiomer. This chapter provides novel ideas for the design of novel
CPL materials in the solution and solid state.
References
1. Bian Z, He Y-B, Gao L-X (2003) Circular dichroism and circularly polarized
photoluminescence spectra of a new chiral conjugated polymers based on 1,1
0 -binaphthyl
structure. Gaodeng Xuexiao Huaxue Xuebao 24:559–561
2. 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'-dihydroxy BINOL:
preliminary measurements of the circularly polarized luminescence. Tetrahedron Lett
55:1760–1764
3. Park J, Yu T, Inagaki T, Akagi K (2015) Helical network polymers exhibiting circularly
polarized luminescence with thermal stability. Synthesis via photo-cross-link polymerizations
of methacrylate derivatives in a chiral nematic liquid crystal. Macromolecules 48:1930–1940
4. Ye Q, Zhu D, Xu L, Lu X, Lu Q (2016) The fabrication of helical fibers with circularly polarized
luminescence via ionic linkage of binaphthol and tetraphenylethylene derivatives. J Mater
Chem C 4:1497–1503
5. Uchida Y, Hirose T, Nakashima T, Kawai T, Matsuda K (2016) Synthesis and photophysical
properties of a 13,13
0 -bibenzo[b]perylenyl derivative as a π-extended 1,1
0 -binaphthyl analog.
Org Lett 18:2118–2121
6. Hirata S, Vacha M (2016) Circularly polarized persistent room-temperature phosphorescence
from metal-free chiral aromatics in air. J Phys Chem Lett 7:1539–1545
7. Shi L, Zhu L, Guo J, Zhang L, Shi Y, Zhang Y, Hou K, Zheng Y, Zhu Y, Lv J et al (2017) Selfassembly of chiral gold clusters into crystalline nanocubes of exceptional optical activity.
Angew Chem Int Ed 56:15397–15401
8. Shintani R, Misawa N, Takano R, Nozaki K (2017) Rhodium-catalyzed synthesis and optical
properties of silicon-bridged arylpyridines. Chem Eur J 23:2660–2665
9. Nishikawa H, Mochizuki D, Higuchi H, Okumura Y, Kikuchi H (2017) Reversible broadspectrum control of selective reflections of chiral nematic phases by closed-/open-type axially
chiral azo dopants. Chem Open 6:710–720
10. Koiso N, Kitagawa Y, Nakanishi T, Fushimi K, Hasegawa Y (2017) Eu(III) chiral coordination
polymer with a structural transformation system. Inorg Chem 56:5741–5747
11. Aoki R, Toyoda R, Kogel JF, Sakamoto R, Kumar J, Kitagawa Y, Harano K, Kawai T,
Nishihara H (2017) Bis(dipyrrinato)zinc(II) complex chiroptical wires: exfoliation into single
strands and intensification of circularly polarized luminescence. J Am Chem Soc
139:16024–16027
2 Circularly Polarized Luminescence of Axially Chiral Binaphthyl Fluorophores
29