57. Shimizu A, Inoue Y, Mori T (2017) A combined experimental and theoretical study on the
circular dichroism of staggered and eclipsed forms of dimethoxy[2.2]-, [3.2]-, and [3.3]
pyridinophanes and their protonated forms. J Phys Chem A 121:8389–8398. https://doi.org/
10.1021/acs.jpca.7b08623
58. Shimizu A, Mori T, Inoue Y, Yamada S (2009) Combined experimental and quantum chemical
investigation of chiroptical properties of nicotinamide derivatives with and without intramolecular cation-π interactions. J Phys Chem A 113:8754–8764. https://doi.org/10.1021/jp904243w
59. Mori T, Grimme S, Inoue Y (2007) A combined experimental and theoretical study on the
conformation of multiarmed chiral aryl ethers. J Org Chem 72:6998–7010. https://doi.org/10.
1021/jo071216n
60. Lovrecek B, Despic A, Bockris JOM (1959) Electrolytic junctions with rectifying properties.
J Phys Chem 63:750–751. https://doi.org/10.1021/j150575a030
61. Kobayashi K, Shirasaka T, Sato A, Horn E, Furukawa N (1999) Self-assembly of a radially
functionalized hexagonal molecule: hexakis(4-hydroxyphenyl)benzene. Angew Chem Int Ed
38:3483–3486.
https://doi.org/10.1002/(SICI)1521-3773(19991203)38:23<3483::AIDANIE3483>3.0.CO;2-A
62. Dale J (1957) Ultraviolet absorption spectra of ortho- and para-linked polyphenyls. Acta Chem
Scand 11:650–659. https://doi.org/10.3891/acta.chem.scand.11-0650
63. Berova N, Bari LD, Pescitelli G (2007) Application of electronic circular dichroism in configurational and conformational analysis of organic compounds. Chem Soc Rev 36:914–931.
https://doi.org/10.1039/B515476F
64. Sakai N, Talukdar P, Matile S (2006) Use of the exciton chirality method in the investigation of
ligand-gated synthetic ion channels. Chirality 18:91–94. https://doi.org/10.1002/chir.20221
65. Berova N, Borhan B, Dong JG, Guo J, Huang X, Karnaukhova E, Kawamura A, Lou J,
Matile S, Nakanishi K, Rickman B, Su J, Tan Q, Zanze I (1998) Solving challenging bioorganic
problems by exciton coupled CD. Pure Appl Chem 70:377–383. https://doi.org/10.1351/
pac199870020377
66. Gust D (1977) Restricted rotation in hexaarylbenzenes. J Am Chem Soc 99:6980–6982. https://
doi.org/10.1021/ja00463a034
67. Kasha M, Rawls HR, El-Bayoumi MA (1965) Exciton model in molecular spectroscopy. Pure
Appl Chem 11:371–392. https://doi.org/10.1351/pac196511030371
68. Jelley E, Spectral E (1936) Absorption and fluorescence of dyes in the molecular state. Nature
138:1009–1010. https://doi.org/10.1038/1381009a0
69. Hobza P (2012) Calculations on noncovalent interactions and databases of benchmark interaction energies. Acc Chem Res 45:663–672. https://doi.org/10.1021/ar200255p
70. Grimme S, Goerigk L, Fink RF (2012) Spin-component-scaled electron correlation methods.
Wiley Interdiscip Rev Comput Mol Sci 2:886–906. https://doi.org/10.1002/wcms.1110
71. Schwabe T, Grimme S (2008) Theoretical thermodynamics for large molecules: walking the
thin line between accuracy and computational cost. Acc Chem Res 41:569–579. https://doi.org/
10.1021/ar700208h
72. Klamt A (2011) The COSMO and COSMO-RS solvation models. Wiley Interdiscip Rev
Comput Mol Sci 1:699–709. https://doi.org/10.1002/wcms.56
73. Gust D, Patton A (1978) Dynamic stereochemistry of hexaarylbenzenes. J Am Chem Soc
100:8175–8181. https://doi.org/10.1021/ja00494a026
74. Sanchez-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 A Eur
J 21:13488–13500. https://doi.org/10.1002/chem.201501178
75. Tanaka H, Inoue Y, Mori T (2018) Circularly polarized luminescence and circular dichroisms in
small organic molecules: correlation between excitation and emission dissymmetry factors.
ChemPhotoChem 2:386–402. https://doi.org/10.1002/cptc.201800015
76. Arroyo IJ, Hu R, Merino G, Tang BZ, Peña-Cabrera E (2009) The smallest and one of the
brightest. Efficient preparation and optical description of the parent borondipyrromethene
system. J Org Chem 74:5719–5722. https://doi.org/10.1021/jo901014w
174
T. Mori
circular dichroism of staggered and eclipsed forms of dimethoxy[2.2]-, [3.2]-, and [3.3]
pyridinophanes and their protonated forms. J Phys Chem A 121:8389–8398. https://doi.org/
10.1021/acs.jpca.7b08623
58. Shimizu A, Mori T, Inoue Y, Yamada S (2009) Combined experimental and quantum chemical
investigation of chiroptical properties of nicotinamide derivatives with and without intramolecular cation-π interactions. J Phys Chem A 113:8754–8764. https://doi.org/10.1021/jp904243w
59. Mori T, Grimme S, Inoue Y (2007) A combined experimental and theoretical study on the
conformation of multiarmed chiral aryl ethers. J Org Chem 72:6998–7010. https://doi.org/10.
1021/jo071216n
60. Lovrecek B, Despic A, Bockris JOM (1959) Electrolytic junctions with rectifying properties.
J Phys Chem 63:750–751. https://doi.org/10.1021/j150575a030
61. Kobayashi K, Shirasaka T, Sato A, Horn E, Furukawa N (1999) Self-assembly of a radially
functionalized hexagonal molecule: hexakis(4-hydroxyphenyl)benzene. Angew Chem Int Ed
38:3483–3486.
https://doi.org/10.1002/(SICI)1521-3773(19991203)38:23<3483::AIDANIE3483>3.0.CO;2-A
62. Dale J (1957) Ultraviolet absorption spectra of ortho- and para-linked polyphenyls. Acta Chem
Scand 11:650–659. https://doi.org/10.3891/acta.chem.scand.11-0650
63. Berova N, Bari LD, Pescitelli G (2007) Application of electronic circular dichroism in configurational and conformational analysis of organic compounds. Chem Soc Rev 36:914–931.
https://doi.org/10.1039/B515476F
64. Sakai N, Talukdar P, Matile S (2006) Use of the exciton chirality method in the investigation of
ligand-gated synthetic ion channels. Chirality 18:91–94. https://doi.org/10.1002/chir.20221
65. Berova N, Borhan B, Dong JG, Guo J, Huang X, Karnaukhova E, Kawamura A, Lou J,
Matile S, Nakanishi K, Rickman B, Su J, Tan Q, Zanze I (1998) Solving challenging bioorganic
problems by exciton coupled CD. Pure Appl Chem 70:377–383. https://doi.org/10.1351/
pac199870020377
66. Gust D (1977) Restricted rotation in hexaarylbenzenes. J Am Chem Soc 99:6980–6982. https://
doi.org/10.1021/ja00463a034
67. Kasha M, Rawls HR, El-Bayoumi MA (1965) Exciton model in molecular spectroscopy. Pure
Appl Chem 11:371–392. https://doi.org/10.1351/pac196511030371
68. Jelley E, Spectral E (1936) Absorption and fluorescence of dyes in the molecular state. Nature
138:1009–1010. https://doi.org/10.1038/1381009a0
69. Hobza P (2012) Calculations on noncovalent interactions and databases of benchmark interaction energies. Acc Chem Res 45:663–672. https://doi.org/10.1021/ar200255p
70. Grimme S, Goerigk L, Fink RF (2012) Spin-component-scaled electron correlation methods.
Wiley Interdiscip Rev Comput Mol Sci 2:886–906. https://doi.org/10.1002/wcms.1110
71. Schwabe T, Grimme S (2008) Theoretical thermodynamics for large molecules: walking the
thin line between accuracy and computational cost. Acc Chem Res 41:569–579. https://doi.org/
10.1021/ar700208h
72. Klamt A (2011) The COSMO and COSMO-RS solvation models. Wiley Interdiscip Rev
Comput Mol Sci 1:699–709. https://doi.org/10.1002/wcms.56
73. Gust D, Patton A (1978) Dynamic stereochemistry of hexaarylbenzenes. J Am Chem Soc
100:8175–8181. https://doi.org/10.1021/ja00494a026
74. Sanchez-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 A Eur
J 21:13488–13500. https://doi.org/10.1002/chem.201501178
75. Tanaka H, Inoue Y, Mori T (2018) Circularly polarized luminescence and circular dichroisms in
small organic molecules: correlation between excitation and emission dissymmetry factors.
ChemPhotoChem 2:386–402. https://doi.org/10.1002/cptc.201800015
76. Arroyo IJ, Hu R, Merino G, Tang BZ, Peña-Cabrera E (2009) The smallest and one of the
brightest. Efficient preparation and optical description of the parent borondipyrromethene
system. J Org Chem 74:5719–5722. https://doi.org/10.1021/jo901014w
174
T. Mori