Synthesis of Optically Active Tolane-Stacked Molecules Based on Planar Chiral [2.2]Paracyclophanes

被引:0
|
作者
Yukimoto, Shun [1 ]
Inoue, Ryo [2 ]
Ito, Takuma [1 ]
Morisaki, Yasuhiro [1 ]
机构
[1] Kwansei Gakuin Univ, Sch Biol & Environm Sci, Dept Appl Chem Environm, 1 Gakuen Uegahara, Sanda, Hyogo 6691330, Japan
[2] Univ Hyogo, Grad Sch Sci, Dept Mat Sci, 3-2-1 Kouto,Kamigori Cho, Akashi, Hyogo 6781297, Japan
关键词
2.2]paracyclophane; planar chirality; circularly polarized luminescence; hydrogen bond; triple helix; RESOLUTION; DERIVATIVES; COMPLEXES; LIGANDS; DIMERS;
D O I
10.1002/ajoc.202400624
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this study, optically active compounds were synthesized by stacking diarylacetylenes with two benzene rings and an ethynylene (tolane derivatives) using planar chiral [2.2]paracyclophanes. The compounds with carboxy groups formed one-dimensional zig-zag structures through hydrogen bonds in the crystals, with three hydrogen-bonded chains bundled to construct a one-handed triple helix. All compounds prepared in this study exhibited circularly polarized luminescence properties with good anisotropy factors.
引用
收藏
页数:7
相关论文
共 50 条
  • [41] Synthesis of optically active through-space conjugated polymers consisting of planar chiral pseudo-meta-disubstituted [2.2]paracyclophane
    Hazuki Maeda
    Ryo Inoue
    Akinori Saeki
    Yasuhiro Morisaki
    Polymer Journal, 2023, 55 : 537 - 545
  • [42] New Types of Planar Chiral [2.2]Paracyclophanes and Construction of One-Handed Double Helices
    Morisaki, Yasuhiro
    Sawada, Risa
    Gon, Masayuki
    Chujo, Yoshiki
    CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (18) : 2524 - 2527
  • [43] Synthesis of Optically Active, X-Shaped, Conjugated Compounds and Dendrimers Based on Planar Chiral [2.2]Paracyclophane, Leading to Highly Emissive Circularly Polarized Luminescence
    Gon, Masayuki
    Morisaki, Yasuhiro
    Sawada, Risa
    Chujo, Yoshiki
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (07) : 2291 - 2298
  • [44] Synthesis and Structure of an Optically Active π-Stacked Poly(dibenzofulvene) Bearing Chiral Terminal Group
    Nakano, Tamaki
    Tanikawa, Mitsuru
    Nakagawa, Osamu
    Yade, Tohru
    Sakamoto, Takeshi
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2009, 47 (01) : 239 - 246
  • [45] Synthesis and circular dichroism of the optically active dendrimers with the planar chiral ferrocene core
    Sokolov, V. I.
    Khrushcheva, N. S.
    Babievsky, K. K.
    Yamskov, I. A.
    RUSSIAN CHEMICAL BULLETIN, 2009, 58 (09) : 1855 - 1857
  • [46] Synthesis and circular dichroism of the optically active dendrimers with the planar chiral ferrocene core
    V. I. Sokolov
    N. S. Khrushcheva
    K. K. Babievsky
    I. A. Yamskov
    Russian Chemical Bulletin, 2009, 58 : 1855 - 1857
  • [47] Synthesis, isolation and structural characterization of optically active planar chiral cyclomercurated ferrocenylimines
    Wu, YJ
    Cui, XL
    Zhou, N
    Song, MP
    Yun, HY
    Du, CX
    Zhu, Y
    TETRAHEDRON-ASYMMETRY, 2000, 11 (24) : 4877 - 4883
  • [48] Crystallization of chiral molecules in optically active solvents
    Tulashie, S.
    Lorenz, H.
    Grandeury, A.
    Seidel-Morgenstern, A.
    BIWIC 2006, 2006, : 238 - 243
  • [49] Planar and central chiral [2.2]paracyclophanes as powerful catalysts for asymmetric 1,2-addition reactions
    Bräse, S
    Dahmen, S
    Höfener, S
    Lauterwasser, F
    Kreis, M
    Ziegert, RE
    SYNLETT, 2004, (15) : 2647 - 2669
  • [50] Asymmetric synthesis and application of planar chiral [2.2]metacyclophanes
    O'Shea, Donal
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245