Synthesis of Carbazole-Based Selenaporphyrin via Annulation

被引：32
|
作者：
Masuda, Motoki [1 ]
Maeda, Chihiro [1 ]
Yoshioka, Naoki [1 ]
机构：
[1] Keio Univ, Dept Appl Chem, Fac Sci & Technol, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 03期
关键词：
STRUCTURAL-CHARACTERIZATION; PORPHYRIN; OLIGOTHIOPHENES; CYCLIZATION; ENEDIYNES; STATE;
D O I：
10.1021/ol303392g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cu(I)-mediated alkoxylation of doubly 1,3-butadiyne-bridged carbazole dimer 1, followed by acid-catalyzed cyclization, provided furan-bridged carbazole dimer 3, while annulation reaction of 1 with selenium in the presence of hydrazine monohydrate provided selenophene-bridged carbazole dimer 5a. Oxidation of isophlorin 5a afforded carbazole-based selenaporphyrin 5b, which possessed distinct aromaticity and produced intensified and red-shifted absorption bands in the near-IR region.
引用
收藏
页码：578 / 581
页数：4
相关论文
共 50 条
  • [41] Carbazole-based coordination polymers of lanthanides and actinides
    Bien, Caitlin
    Manke, David
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [42] Acyclic indole and carbazole-based sulfate receptors
    Gale, Philip A.
    Hiscock, Jennifer R.
    Jie, Chen Zhu
    Hursthouse, Michael B.
    Light, Mark E.
    CHEMICAL SCIENCE, 2010, 1 (02) : 215 - 220
  • [43] Synthesis of carbazole-based BODIPY dimers showing red fluorescence in the solid state
    Maeda, Chihiro
    Todaka, Takumi
    Ueda, Tomomi
    Ema, Tadashi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (44) : 9283 - 9287
  • [44] Synthesis and optoelectronic properties of amino-functionalized carbazole-based conjugated polymers
    ShengJian Liu
    ZhiPeng Zhang
    DongCheng Chen
    ChunHui Duan
    JunMing Lu
    Jie Zhang
    Fei Huang
    ShiJian Su
    JunWu Chen
    Yong Cao
    Science China Chemistry, 2013, 56 : 1119 - 1128
  • [45] Synthesis, Functionalization, and Optical Properties of Chiral Carbazole-Based Diaza[6]helicenes
    Bucinskas, Audrius
    Waghray, Deepali
    Bagdziunas, Gintautas
    Thomas, Joice
    Grazulevicius, Juozas Vidas
    Dehaen, Wim
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (05): : 2521 - 2528
  • [46] Design and One-pot Synthesis of Novel Carbazole-based Thiazolone Imines
    Borge, Vikas V.
    Aldar, Darshana D.
    Nangare, Gajanan S.
    Chavan, Pranali A.
    Thorat, Ramchandra G.
    Bangade, Vikas M.
    Popatkar, Bhushan B.
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2025, 57 (02) : 154 - 162
  • [47] Carbazole-Based Tetrapodal Anchor Groups for Gold Surfaces: Synthesis and Conductance Properties
    O'Driscoll, Luke J.
    Wang, Xintai
    Jay, Michael
    Batsanov, Andrei S.
    Sadeghi, Hatef
    Lambert, Colin J.
    Robinson, Benjamin J.
    Bryce, Martin R.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (02) : 882 - 889
  • [48] Multiply colored electrochromic carbazole-based polymers
    Sotzing, GA
    Reddinger, JL
    Katritzky, AR
    Soloducho, J
    Musgrave, R
    Reynolds, JR
    Steel, PJ
    CHEMISTRY OF MATERIALS, 1997, 9 (07) : 1578 - 1587
  • [49] Synthesis and studies of carbazole-based donor polymer for organic solar cell applications
    Govindasamy Sathiyan
    Govindasamy Siva
    E. K. T. Sivakumar
    Jai Prakash
    Hendrik C. Swart
    Pachagounder Sakthivel
    Colloid and Polymer Science, 2018, 296 : 1193 - 1203
  • [50] Synthesis and studies of carbazole-based donor polymer for organic solar cell applications
    Sathiyan, Govindasamy
    Siva, Govindasamy
    Sivakumar, E. K. T.
    Prakash, Jai
    Swart, Hendrik C.
    Sakthivel, Pachagounder
    COLLOID AND POLYMER SCIENCE, 2018, 296 (07) : 1193 - 1203
12345