ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Phenanthrylene-butadiynylene and Phenanthrylene-thienylene Macrocycles: Synthesis, Structure, and Properties

View Author Information
Department of Chemistry, Faculty of Science, Masaryk University, Kotlářská 2, 611 37 Brno, Czech Republic
CEITEC - Central European Institute of Technology, Masaryk University, Kamenice 5, 625 00 Brno-Bohunice, Czech Republic
Cite this: J. Org. Chem. 2016, 81, 15, 6244–6252
Publication Date (Web):July 11, 2016
https://doi.org/10.1021/acs.joc.6b00814
Copyright © 2016 American Chemical Society

    Article Views

    1626

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Read OnlinePDF (1 MB)
    Supporting Info (2)»

    Abstract

    Abstract Image

    A series of macrocycles consisting of 9,10-substituted phenanthrenes connected by butadiynylene linkers in positions 3 and 6 has been described as well as their transformation into the corresponding phenanthrylene-thienylene macrocycles. Structure and properties of the macrocycles, such as self-association in solution and optical and electrochemical properties, were studied and reported in a comparative manner with respect to the effects of the different sizes and shapes of the macrocycles and the character and length of their side chains.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.joc.6b00814.

    • Copies of 1H and 13C NMR spectra of all new compounds; calculation of self-association constants, UV–vis absorption and emission spectra, cyclic voltammetry details, DFT calculations, and X-ray structure details; and comparison of calculated and experimental MS isotopic distributions of prepared macrocycles (PDF)

    • X-ray crystallographic data for compound 1e (CIF)

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 15 publications.

    1. Katarzyna Wypych, Maria Dimitrova, Dage Sundholm, Miłosz Pawlicki. Diagnosing Ring Current(s) in Figure-Eight Skeletons: A 3D Through-Space Conjugation in the Two-Loops Crossing. Organic Letters 2022, 24 (27) , 4876-4880. https://doi.org/10.1021/acs.orglett.2c01625
    2. Arseni Borissov, Yogesh Kumar Maurya, Liliia Moshniaha, Wai-Shing Wong, Marika Żyła-Karwowska, Marcin Stępień. Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds. Chemical Reviews 2022, 122 (1) , 565-788. https://doi.org/10.1021/acs.chemrev.1c00449
    3. Yi Liu, Fa Xu Lin, Yang Feng, Xiaoqing Liu, Lei Wang, Zhen-Qiang Yu, Ben Zhong Tang. Shape-Persistent π-Conjugated Macrocycles with Aggregation-Induced Emission Property: Synthesis, Mechanofluorochromism, and Mercury(II) Detection. ACS Applied Materials & Interfaces 2019, 11 (37) , 34232-34240. https://doi.org/10.1021/acsami.9b10702
    4. Yong Yang, Ming Chu, Qian Miao. From Phenanthrylene Butadiynylene Macrocycles to S-Heterocycloarenes. Organic Letters 2018, 20 (14) , 4259-4262. https://doi.org/10.1021/acs.orglett.8b01668
    5. Qi Qu, Meigui Fu, Caixia Lin, Yanhou Geng, Yuanming Li, Yaofeng Yuan. Synthesis, properties and application of o -carborane-based π-conjugated macrocycles. Organic Chemistry Frontiers 2023, 10 (13) , 3293-3299. https://doi.org/10.1039/D3QO00487B
    6. Dongyue An, Yutao Sun, Dongdong Chang, Jiangyu Zhu, Shumin Chen, Xuefeng Lu. Naphthalimide-based conjugated macrocycles possessing tunable self-assembly and supramolecular binding behaviours. Frontiers in Chemistry 2022, 10 https://doi.org/10.3389/fchem.2022.1094828
    7. Fei Zeng, Lu Cheng, Wei-Jun Zhang, Lin-Li Tang, Xiao-Feng Wang. Phenanthrene[2]arene: synthesis and application as nonporous adaptive crystals in the separation of benzene from cyclohexane. Organic Chemistry Frontiers 2022, 9 (12) , 3307-3311. https://doi.org/10.1039/D2QO00474G
    8. Rodrigo M. Barba-Barba, Marwa Chammam, Gabriel Ramos-Ortiz, Dymytrii Listunov, Jayaramakrishnan Velusamy, Mario Rodriguez, Ramon Carriles, Carlos Silva, Carine Duhayon, Brice Kauffmann, Valérie Maraval, Remi Chauvin. Linear and nonlinear optical properties of a quadrupolar carbo-benzene and its benzenic parent: The carbo-merization effect. Dyes and Pigments 2021, 188 , 109133. https://doi.org/10.1016/j.dyepig.2021.109133
    9. Jikai Wen, Yijiang Liu, Hongbiao Chen, Mei Yang, Huaming Li. Synthesis and characterization of phenanthroimidazole-containing triazine frameworks and their performance in CO2 capture. Microporous and Mesoporous Materials 2021, 316 , 110939. https://doi.org/10.1016/j.micromeso.2021.110939
    10. Andrea Preuß, Sebastian Notz, Eduard Kovalski, Marcus Korb, Thomas Blaudeck, Xiao Hu, Jörg Schuster, Dominique Miesel, Tobias Rüffer, Alexander Hildebrandt, Katja Schreiter, Stefan Spange, Stefan E. Schulz, Heinrich Lang. Ferrocenyl‐Pyrenes, Ferrocenyl‐9,10‐Phenanthrenediones, and Ferrocenyl‐9,10‐Dimethoxyphenanthrenes: Charge‐Transfer Studies and SWCNT Functionalization. Chemistry – A European Journal 2020, 26 (12) , 2635-2652. https://doi.org/10.1002/chem.201904450
    11. Xuefeng Lu, Tullimilli Y. Gopalakrishna, Hoa Phan, Tun Seng Herng, Qing Jiang, Chunchen Liu, Guangwu Li, Jun Ding, Jishan Wu. Global Aromaticity in Macrocyclic Cyclopenta‐Fused Tetraphenanthrenylene Tetraradicaloid and Its Charged Species. Angewandte Chemie 2018, 130 (40) , 13236-13240. https://doi.org/10.1002/ange.201807185
    12. Xuefeng Lu, Tullimilli Y. Gopalakrishna, Hoa Phan, Tun Seng Herng, Qing Jiang, Chunchen Liu, Guangwu Li, Jun Ding, Jishan Wu. Global Aromaticity in Macrocyclic Cyclopenta‐Fused Tetraphenanthrenylene Tetraradicaloid and Its Charged Species. Angewandte Chemie International Edition 2018, 57 (40) , 13052-13056. https://doi.org/10.1002/anie.201807185
    13. Bhimrao Vaijnath Phulwale, Sushil Kumar Mishra, Ctibor Mazal. Synthesis and properties of π-conjugated donor–acceptor macrocycles derived from phenanthrylene building blocks. Tetrahedron 2018, 74 (27) , 3616-3623. https://doi.org/10.1016/j.tet.2018.05.025
    14. Ikumi Sako, Naoki Kishimoto, Hiroyuki Otani, Tomohiko Nishiuchi, Hideyuki Shimizu, Masahiko Iyoda. Synthesis of Cyclic Oligomers of 4,4′′-Diethynyl-4′,5′-dioctyl- o -terphenyl Using Eglington Coupling Reaction: Formation of Large Cyclic Oligomers as Major Products under Standard Conditions. Bulletin of the Chemical Society of Japan 2017, 90 (11) , 1244-1250. https://doi.org/10.1246/bcsj.20170179
    15. Edward R. Biehl. Five-Membered Ring Systems. 2017, 147-182. https://doi.org/10.1016/B978-0-08-102310-5.00005-9

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect