Second hyperpolarizabilities of polycyclic diphenalenyl radicals: Effects of para/ortho-quinoid structures and central ring modification

Masayoshi Nakano; Nozomi Nakagawa; Suguru Ohta; Ryohei Kishi; Takashi Kubo; Kenji Kamada; Koji Ohta; Benoît Champagne; Edith Botek; Hideaki Takahashi; Shin ichi Furukawa; Yasushi Morita; Kazuhiro Nakasuji; Kizashi Yamaguchi

doi:10.1016/j.cplett.2006.07.065

Second hyperpolarizabilities of polycyclic diphenalenyl radicals: Effects of para/ortho-quinoid structures and central ring modification

Masayoshi Nakano, Nozomi Nakagawa, Suguru Ohta, Ryohei Kishi, Takashi Kubo, Kenji Kamada, Koji Ohta, Benoît Champagne, Edith Botek, Hideaki Takahashi, Shin ichi Furukawa, Yasushi Morita, Kazuhiro Nakasuji, Kizashi Yamaguchi

Unit of theoretical and structural physico-chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

We have investigated the structural dependence of static second hyperpolarizabilities (γ) of polycyclic diphenalenyl radicals, i.e., IDPL, as-IDPL and TDPL, using the hybrid density functional theory method. It turns out that the diradical character of as-IDPL (0.923) is larger than that of IDPL (0.770) and is close to 1 (pure diradical state), which supports the fact that the γ of as-IDPL (472 × 10³ a.u.) is smaller than that of IDPL (2284 × 10³ a.u.). The replacement of a central benzene ring (as-IDPL) by a thiophene ring (TDPL) increases the γ (1375 × 10³ a.u.). This is predicted to be caused by the reduction of aromaticity of the central ring and by the hypervalency of the sulfur atom of the thiophene.

Original language	English
Pages (from-to)	174-179
Number of pages	6
Journal	Chemical Physics Letters
Volume	429
Issue number	1-3
DOIs	https://doi.org/10.1016/j.cplett.2006.07.065
Publication status	Published - 29 Sept 2006

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Nakano, M., Nakagawa, N., Ohta, S., Kishi, R., Kubo, T., Kamada, K., Ohta, K., Champagne, B., Botek, E., Takahashi, H., Furukawa, S. I., Morita, Y., Nakasuji, K., & Yamaguchi, K. (2006). Second hyperpolarizabilities of polycyclic diphenalenyl radicals: Effects of para/ortho-quinoid structures and central ring modification. Chemical Physics Letters, 429(1-3), 174-179. https://doi.org/10.1016/j.cplett.2006.07.065

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title = "Second hyperpolarizabilities of polycyclic diphenalenyl radicals: Effects of para/ortho-quinoid structures and central ring modification",

abstract = "We have investigated the structural dependence of static second hyperpolarizabilities (γ) of polycyclic diphenalenyl radicals, i.e., IDPL, as-IDPL and TDPL, using the hybrid density functional theory method. It turns out that the diradical character of as-IDPL (0.923) is larger than that of IDPL (0.770) and is close to 1 (pure diradical state), which supports the fact that the γ of as-IDPL (472 × 103 a.u.) is smaller than that of IDPL (2284 × 103 a.u.). The replacement of a central benzene ring (as-IDPL) by a thiophene ring (TDPL) increases the γ (1375 × 103 a.u.). This is predicted to be caused by the reduction of aromaticity of the central ring and by the hypervalency of the sulfur atom of the thiophene.",

author = "Masayoshi Nakano and Nozomi Nakagawa and Suguru Ohta and Ryohei Kishi and Takashi Kubo and Kenji Kamada and Koji Ohta and Beno{\^i}t Champagne and Edith Botek and Hideaki Takahashi and Furukawa, {Shin ichi} and Yasushi Morita and Kazuhiro Nakasuji and Kizashi Yamaguchi",

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Nakano, M, Nakagawa, N, Ohta, S, Kishi, R, Kubo, T, Kamada, K, Ohta, K, Champagne, B, Botek, E, Takahashi, H, Furukawa, SI, Morita, Y, Nakasuji, K & Yamaguchi, K 2006, 'Second hyperpolarizabilities of polycyclic diphenalenyl radicals: Effects of para/ortho-quinoid structures and central ring modification', Chemical Physics Letters, vol. 429, no. 1-3, pp. 174-179. https://doi.org/10.1016/j.cplett.2006.07.065

TY - JOUR

T1 - Second hyperpolarizabilities of polycyclic diphenalenyl radicals

T2 - Effects of para/ortho-quinoid structures and central ring modification

AU - Nakano, Masayoshi

AU - Nakagawa, Nozomi

AU - Ohta, Suguru

AU - Kishi, Ryohei

AU - Kubo, Takashi

AU - Kamada, Kenji

AU - Ohta, Koji

AU - Champagne, Benoît

AU - Botek, Edith

AU - Takahashi, Hideaki

AU - Furukawa, Shin ichi

AU - Morita, Yasushi

AU - Nakasuji, Kazuhiro

AU - Yamaguchi, Kizashi

PY - 2006/9/29

Y1 - 2006/9/29

N2 - We have investigated the structural dependence of static second hyperpolarizabilities (γ) of polycyclic diphenalenyl radicals, i.e., IDPL, as-IDPL and TDPL, using the hybrid density functional theory method. It turns out that the diradical character of as-IDPL (0.923) is larger than that of IDPL (0.770) and is close to 1 (pure diradical state), which supports the fact that the γ of as-IDPL (472 × 103 a.u.) is smaller than that of IDPL (2284 × 103 a.u.). The replacement of a central benzene ring (as-IDPL) by a thiophene ring (TDPL) increases the γ (1375 × 103 a.u.). This is predicted to be caused by the reduction of aromaticity of the central ring and by the hypervalency of the sulfur atom of the thiophene.

AB - We have investigated the structural dependence of static second hyperpolarizabilities (γ) of polycyclic diphenalenyl radicals, i.e., IDPL, as-IDPL and TDPL, using the hybrid density functional theory method. It turns out that the diradical character of as-IDPL (0.923) is larger than that of IDPL (0.770) and is close to 1 (pure diradical state), which supports the fact that the γ of as-IDPL (472 × 103 a.u.) is smaller than that of IDPL (2284 × 103 a.u.). The replacement of a central benzene ring (as-IDPL) by a thiophene ring (TDPL) increases the γ (1375 × 103 a.u.). This is predicted to be caused by the reduction of aromaticity of the central ring and by the hypervalency of the sulfur atom of the thiophene.

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DO - 10.1016/j.cplett.2006.07.065

M3 - Article

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SN - 0009-2614

VL - 429

SP - 174

EP - 179

JO - Chemical Physics Letters

JF - Chemical Physics Letters

IS - 1-3

ER -

Second hyperpolarizabilities of polycyclic diphenalenyl radicals: Effects of para/ortho-quinoid structures and central ring modification

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