Norcorroles as antiaromatic π-electronic systems that form dimension-controlled assemblies

被引:5
作者
Ishikawa, Soh [1 ]
Yamasumi, Kazuhisa [1 ]
Sugiura, Shinya [1 ]
Sato, Shunsuke [2 ]
Watanabe, Go [2 ,3 ]
Koo, Yun Hee [4 ]
Seki, Shu [4 ]
Bando, Yuya [1 ]
Haketa, Yohei [1 ]
Shinokubo, Hiroshi [5 ]
Maeda, Hiromitsu [1 ]
机构
[1] Ritsumeikan Univ, Coll Life Sci, Dept Appl Chem, Kusatsu 5258577, Japan
[2] Kitasato Univ, Sch Sci, Dept Phys, Sagamihara 2520373, Japan
[3] Kitasato Univ, Sch Frontier Engn, Dept Data Sci, Sagamihara 2520373, Japan
[4] Kyoto Univ, Grad Sch Engn, Dept Mol Engn, Kyoto 6158510, Japan
[5] Nagoya Univ, Grad Sch Engn, Dept Mol & Macromol Chem, Nagoya 4648603, Japan
基金
日本学术振兴会;
关键词
DISCOTIC LIQUID-CRYSTALS; TRANSITION-METAL-COMPLEXES; TRANSPORT PROPERTIES; DIFFRACTOMETRY; MESOMORPHISM; ABSORPTION; PORPHYRIN; BEHAVIOR;
D O I
10.1039/d4sc01633e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Norcorrole derivatives with 3,4,5-trialkoxyphenyl moieties at the meso positions were synthesized to form various stacking assemblies in single crystals and thermotropic liquid crystals (LCs) depending on aliphatic chain lengths. Triple-decker stacking structures were formed via the interactions between the antiaromatic systems formed for the butoxy and dodecyloxy derivatives in the single-crystal and LC states, respectively. In particular, the LC state exhibited discotic columnar structures comprising triple deckers to exhibit high electric conductivity, as supported by molecular dynamics simulations. Norcorroles with 3,4,5-trialkoxyphenyl moieties were synthesized to form thermotropic liquid crystals (LCs), in which triple-decker stacking structures were formed. The LC state exhibited discotic columnar structures to exhibit high electric conductivity.
引用
收藏
页码:7603 / 7609
页数:7
相关论文
共 37 条
[1]  
[Anonymous], 2012, Topics in Current Chemistry, V312, P1, DOI [10.1007/978-3-642-27284-4, DOI 10.1007/978-3-642-27284-4]
[2]   Liquid Crystals: Versatile Self-Organized Smart Soft Materials [J].
Bisoyi, Hari Krishna ;
Li, Quan .
CHEMICAL REVIEWS, 2022, 122 (05) :4887-4926
[3]   Norcorrole:: Observation of the smallest porphyrin variant with a N4 core [J].
Broering, Martin ;
Koehler, Silke ;
Kleeberg, Christian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (30) :5658-5660
[4]  
Frisch M. J., 2016, GAUSSIAN 16 REVISION
[5]   Light absorption and hole-transport properties of copper corroles: from aggregates to a liquid crystal mesophase [J].
Gao, Di ;
Edzang, Judicaelle Andeme ;
Diallo, Abdou Karim ;
Dutronc, Thibault ;
Balaban, Teodor Silviu ;
Videlot-Ackermann, Christine ;
Terazzi, Emmanuel ;
Canard, Gabriel .
NEW JOURNAL OF CHEMISTRY, 2015, 39 (09) :7140-7146
[6]   Anisotropy of the induced current density (ACID), a general method to quantify and visualize electronic delocalization [J].
Geuenich, D ;
Hess, K ;
Köhler, F ;
Herges, R .
CHEMICAL REVIEWS, 2005, 105 (10) :3758-3772
[7]   Delocalization of electrons in molecules [J].
Herges, R ;
Geuenich, D .
JOURNAL OF PHYSICAL CHEMISTRY A, 2001, 105 (13) :3214-3220
[8]   THE NATURE OF PI-PI INTERACTIONS [J].
HUNTER, CA ;
SANDERS, JKM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (14) :5525-5534
[9]   Discotic liquid crystals of transition metal complexes 37: a thermotropic cubic mesophase having Pn3m symmetry exhibited by phthalocyanine-based derivatives [J].
Ichihara, Masahiro ;
Suzuki, Ayumi ;
Hatsusaka, Kazuaki ;
Ohta, Kazuchika .
LIQUID CRYSTALS, 2007, 34 (05) :555-567
[10]   Gram-Scale Synthesis of Nickel(II) Norcorrole: The Smallest Antiaromatic Porphyrinoid [J].
Ito, Tomohiro ;
Hayashi, Yosuke ;
Shimizu, Soji ;
Shin, Ji-Young ;
Kobayashi, Nagao ;
Shinokubo, Hiroshi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (34) :8542-8545