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Article

Donor-Type Nickel–Dithiolene Complexes Fused with Bulky Cycloalkane Substituents and Their Application in Molecular Conductors

by
Kazuya Kubo
1,*,
Mamoru Sadahiro
1,
Sonomi Arata
1,
Norihisa Hoshino
2,
Tomofumi Kadoya
1,
Tomoyuki Akutagawa
2,
Reizo Kato
3 and
Jun-ichi Yamada
1
1
Graduate School of Science, University of Hyogo, 3-2-1, Kouto, Kamigori-cho, Akou-gun, Kobe 678-1297, Japan
2
Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan
3
RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0023, Japan
*
Author to whom correspondence should be addressed.
Crystals 2021, 11(10), 1154; https://doi.org/10.3390/cryst11101154
Submission received: 26 August 2021 / Revised: 13 September 2021 / Accepted: 14 September 2021 / Published: 23 September 2021
(This article belongs to the Special Issue Organic Conductors)
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Abstract

The effects of substituents on the arrangement of metal–dithiolene complexes based on π-conjugated systems, which are extensively used to synthesize various functional materials, have not been studied adequately. New donor-type nickel–dithiolene complexes fused with bulky cycloalkane substituents [Ni(Cn-dddt)2] (C5-dddt = 4a,5,6,6a-pentahydro-1,4-benzodithiin-2,3-dithiolate; C6-dddt = 4a,5,6,7,8,8a-hexahydro-1,4-benzodithiin-2,3-dithiolate; C7-dddt = 4a,5,6,7,8,9,9a-heptahydro-1,4-benzodithiin-2,3-dithiolate; and C8-dddt = 4a,5,6,7,8,9,10,10a-octahydro-1,4-benzodithiin-2,3-dithiolate) were synthesized in this study. All the complexes were crystallized in cis-[Ni(cis-Cn-dddt)2] conformations with cis-oriented (R,S) conformations around the cycloalkylene groups in the neutral state. Unique molecular arrangements with a three-dimensional network, a one-dimensional column, and a helical molecular arrangement were formed in the crystals owing to the flexible cycloalkane moieties. New 2:1 cation radical crystals of [Ni(C5-dddt)2]2(X) (X = ClO4− or PF6−), obtained by electrochemical crystallization, exhibited semiconducting behaviors (ρrt = 0.8 Ω cm, Ea = 0.09 eV for the ClO4− crystal; 4.0 Ω cm, 0.13 eV for the PF6− crystal) under ambient pressure due to spin-singlet states between the dimers of the donor, which were in accordance with the conducting behaviors under hydrostatic pressure (ρrt = 0.2 Ω cm, Ea = 0.07 eV for the ClO4− crystal; 1.0 Ω cm, 0.12 eV for the PF6− crystal at 2.0 GPa).
Keywords: nickel–dithiolene complex; cycloalkane substituent; molecular conductor nickel–dithiolene complex; cycloalkane substituent; molecular conductor

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MDPI and ACS Style

Kubo, K.; Sadahiro, M.; Arata, S.; Hoshino, N.; Kadoya, T.; Akutagawa, T.; Kato, R.; Yamada, J.-i. Donor-Type Nickel–Dithiolene Complexes Fused with Bulky Cycloalkane Substituents and Their Application in Molecular Conductors. Crystals 2021, 11, 1154. https://doi.org/10.3390/cryst11101154

AMA Style

Kubo K, Sadahiro M, Arata S, Hoshino N, Kadoya T, Akutagawa T, Kato R, Yamada J-i. Donor-Type Nickel–Dithiolene Complexes Fused with Bulky Cycloalkane Substituents and Their Application in Molecular Conductors. Crystals. 2021; 11(10):1154. https://doi.org/10.3390/cryst11101154

Chicago/Turabian Style

Kubo, Kazuya, Mamoru Sadahiro, Sonomi Arata, Norihisa Hoshino, Tomofumi Kadoya, Tomoyuki Akutagawa, Reizo Kato, and Jun-ichi Yamada. 2021. "Donor-Type Nickel–Dithiolene Complexes Fused with Bulky Cycloalkane Substituents and Their Application in Molecular Conductors" Crystals 11, no. 10: 1154. https://doi.org/10.3390/cryst11101154

APA Style

Kubo, K., Sadahiro, M., Arata, S., Hoshino, N., Kadoya, T., Akutagawa, T., Kato, R., & Yamada, J.-i. (2021). Donor-Type Nickel–Dithiolene Complexes Fused with Bulky Cycloalkane Substituents and Their Application in Molecular Conductors. Crystals, 11(10), 1154. https://doi.org/10.3390/cryst11101154

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