Synthesis and photophysical properties of bi-aza[5]helicene and bi-aza[6]helicene

被引:17
|
作者
Upadhyay, Gourav M. [1 ]
Bedekar, Ashutosh V. [1 ]
机构
[1] Maharaja Sayajirao Univ Baroda, Dept Chem, Fac Sci, Vadodara 390002, India
关键词
Bi-aza[n]helicene; Photocyclization; Fluorescence spectroscopy; ONE HUNDRED YEARS; PYRIDINE N-OXIDES; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE SYNTHESES; CHIRAL RECOGNITION; ELECTRON-RICH; BIS-OXAZINES; HELICENE; RESOLUTION; AGGREGATION;
D O I
10.1016/j.tet.2015.06.040
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of two derivatives of bi-aza[n]helicenes is achieved by I-2-THF mediated photocyclization of corresponding bi-styryl derivatives. The cyclization furnished the desired angularly fused bi-aza[5] helicene and bi-aza[6]helicene in moderate yields. The structures are established by NMR spectroscopy and single crystal X-ray analysis. The crystal structure indicate an unusually planer central biphenyl unit in the bi-aza[6]helicene. It also indicates to the presence of 'P' and 'M' stereoisomer in the bi-aza[6] helicene making it a meso isomer. The series of synthesized bi-aza[n]helicenes were characterized by UV and fluorescence spectroscopy. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5644 / 5649
页数:6
相关论文
共 43 条
  • [21] Synthesis, X-ray analysis and photophysical properties of a new N-containing pentacyclic helicene
    Ben Braiek, Mourad
    Aloui, Faouzi
    Moussa, Souad
    Tounsi, Moncef
    Marrot, Jerome
    Ben Hassine, Bechir
    TETRAHEDRON LETTERS, 2013, 54 (40) : 5421 - 5425
  • [22] A Scalable and Expedient Route to 1-Aza[6]helicene Derivatives and Its Subsequent Application to a Chiral-Relay Asymmetric Strategy
    Weimar, Marko
    da Costa, Rosenildo Correa
    Lee, Fu-Howe
    Fuchter, Matthew J.
    ORGANIC LETTERS, 2013, 15 (07) : 1706 - 1709
  • [23] A Combined Experimental and Theoretical Study on the Stereodynamics of Monoaza[5]helicenes: Solvent-Induced Increase of the Enantiomerization Barrier in 1-Aza-[5]helicene
    Caronna, Tullio
    Mele, Andrea
    Famulari, Antonino
    Mendola, Daniele
    Fontana, Francesca
    Juza, Markus
    Kamuf, Matthias
    Zawatzky, Kerstin
    Trapp, Oliver
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (40) : 13919 - 13924
  • [24] A phenothiazine-fused electroactive bilayer helicene: design, synthesis, ACQ-to-AIE transformation and photophysical properties
    Shivaji, Babar Suraj
    Boddula, Rajamouli
    Saeki, Akinori
    Singh, Surya Prakash
    JOURNAL OF MATERIALS CHEMISTRY C, 2022, 10 (13) : 5173 - 5182
  • [25] SYNTHESIS, X-RAY ANALYSIS, AND EVALUATION OF THE OPTOELECTRONIC PROPERTIES OF A NEW THIA[6]HELICENE
    Moussa, Souad
    Aloui, Faouzi
    Retailleau, Pascal
    Ben Hassine, Bechir
    SYNTHETIC COMMUNICATIONS, 2012, 42 (07) : 1010 - 1018
  • [26] π-Expanded [6]Helicene-Containing Nanographenes: Synthesis, Structures, and Chiroptical Properties
    Ye, Tongtong
    Li, Yiming
    Shi, Yanwei
    Che, Yi
    Leng, Bihan
    Wang, Sujuan
    Xiao, Jinchong
    ORGANIC LETTERS, 2024, 26 (34) : 7088 - 7093
  • [27] Copper-catalyzed modular synthesis of aromatic-interrupted Aza[6]helicenes with chiroptical properties
    Han, Yingqi
    Wu, Chao
    Chen, Chao
    CELL REPORTS PHYSICAL SCIENCE, 2025, 6 (01):
  • [28] Aza[5]helicene Rivals N-Annulated Perylene as π-Linker of D-π-D Typed Hole-Transporters for Perovskite Solar Cells
    Wang, Jianan
    Shi, Huilei
    Xu, Niansheng
    Zhang, Jing
    Yuan, Yi
    Lei, Ming
    Wang, Lidong
    Wang, Peng
    ADVANCED FUNCTIONAL MATERIALS, 2020, 30 (30)
  • [29] Assembly of [5]Helicene Subunits by Palladium-Catalyzed Reactions: Synthesis, Structures, Properties, and Theoretical Study of Multiple Helicenes
    Hosokawa, Tomoka
    Tsurusaki, Akihiro
    Kamikawa, Ken
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2020, 78 (11) : 1013 - 1020
  • [30] 2,13-Diaza[5]helicene: synthesis, theoretical calculations and spectroscopic properties
    Caronna, Tullio
    Fontana, Francesca
    Longhi, Giovanna
    Mele, Andrea
    Natali Sora, Isabella
    Vigano, Luca
    ARKIVOC, 2009, : 145 - 155