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
ACS Publications. Most Trusted. Most Cited. Most Read
Single-Site Modifications and Their Effect on the Folding Stability of m-Phenylene Ethynylene Oligomers
My Activity
    Letter

    Single-Site Modifications and Their Effect on the Folding Stability of m-Phenylene Ethynylene Oligomers
    Click to copy article linkArticle link copied!

    View Author Information
    Department of Chemistry and Materials Science & Engineering, 600 South Mathews Avenue, The University of Illinois at Urbana-Champaign, Urbana, Illinois 61801
    Other Access OptionsSupporting Information (1)

    Organic Letters

    Cite this: Org. Lett. 2004, 6, 6, 889–892
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol036376+
    Published February 21, 2004
    Copyright © 2004 American Chemical Society

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    The folded structure of a m-phenylene ethynylene oligomer is tolerant to single-site modifications to both the backbone sequence and end groups. The helical structure is reinforced by multiple noncovalent interactions, allowing the oligomer sequence to be customized without a significant change in stability in most cases. The small changes that are observed are consistent with the expected behavior of π-stacked systems and demonstrate subtle control over folding through single-site modifications.

    Copyright © 2004 American Chemical Society

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    *

    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

    Supporting Information Available

    Click to copy section linkSection link copied!

    Detailed descriptions of all experimental procedures and accompanying analytical data. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Electronic Supporting Information files are available without a subscription to ACS Web Editions. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Information. Files available from the ACS website may be downloaded for personal use only. Users are not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information from the ACS website, either in whole or in part, in either machine-readable form or any other form without permission from the American Chemical Society. For permission to reproduce, republish and redistribute this material, requesters must process their own requests via the RightsLink permission system. Information about how to use the RightsLink permission system can be found at http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!

    This article is cited by 31 publications.

    1. Sourav Bhowmick, Achintya Jana, Khushwant Singh, Prerak Gupta, Ankit Gangrade, Biman B. Mandal, Neeladri Das. Coordination-Driven Self-Assembly of Ionic Irregular Hexagonal Metallamacrocycles via an Organometallic Clip and Their Cytotoxicity Potency. Inorganic Chemistry 2018, 57 (7) , 3615-3625. https://doi.org/10.1021/acs.inorgchem.7b01561
    2. Sourav Bhowmick, Sourav Chakraborty, Atanu Das, P. R. Rajamohanan, and Neeladri Das . Pyrazine-Based Organometallic Complex: Synthesis, Characterization, and Supramolecular Chemistry. Inorganic Chemistry 2015, 54 (6) , 2543-2550. https://doi.org/10.1021/ic502581x
    3. Sean W. Robinson, Chantal L. Mustoe, Nicholas G. White, Asha Brown, Amber L. Thompson, Pierre Kennepohl, and Paul D. Beer . Evidence for Halogen Bond Covalency in Acyclic and Interlocked Halogen-Bonding Receptor Anion Recognition. Journal of the American Chemical Society 2015, 137 (1) , 499-507. https://doi.org/10.1021/ja511648d
    4. Motonori Banno, Tomoko Yamaguchi, Kanji Nagai, Christian Kaiser, Stefan Hecht, and Eiji Yashima . Optically Active, Amphiphilic Poly(meta-phenylene ethynylene)s: Synthesis, Hydrogen-Bonding Enforced Helix Stability, and Direct AFM Observation of Their Helical Structures. Journal of the American Chemical Society 2012, 134 (20) , 8718-8728. https://doi.org/10.1021/ja303204m
    5. Nozomi Saito, Ryo Terakawa, Masanori Shigeno, Ryo Amemiya, and Masahiko Yamaguchi . Side Chain Effect on the Double Helix Formation of Ethynylhelicene Oligomers. The Journal of Organic Chemistry 2011, 76 (12) , 4841-4858. https://doi.org/10.1021/jo200658q
    6. Veluru Ramesh Naidu, Min Cheol Kim, Jae-min Suk, Ho-Joong Kim, Myongsoo Lee, Eunji Sim and Kyu-Sung Jeong. Biased Helical Folding of Chiral Oligoindole Foldamers. Organic Letters 2008, 10 (23) , 5373-5376. https://doi.org/10.1021/ol8022243
    7. Takakazu Yamamoto,, Masahiro Abe,, Biyao Wu,, Byoung-Ki Choi,, Yosuke Harada,, Yasuo Takahashi,, Kentaro Kawata,, Shintaro Sasaki, and, Kenji Kubota. Basic Information on Nonsubstituted Polyphenylene and Polythiophene Obtained via Solubilization of Polymers. Macromolecules 2007, 40 (15) , 5504-5512. https://doi.org/10.1021/ma0626517
    8. Iwao Okamoto,, Mayumi Nabeta,, Yasuko Hayakawa,, Nobuyoshi Morita,, Tetsuya Takeya,, Hyuma Masu,, Isao Azumaya, and, Osamu Tamura. Acid-Induced Molecular Folding and Unfolding of N-Methyl Aromatic Amide Bearing 2,6-Disubstituted Pyridines. Journal of the American Chemical Society 2007, 129 (7) , 1892-1893. https://doi.org/10.1021/ja0682879
    9. Hyuma Masu,, Ikuko Mizutani,, Takako Kato,, Isao Azumaya,, Kentaro Yamaguchi,, Keiki Kishikawa, and, Shigeo Kohmoto. Naphthalene- and Anthracene-Based Aromatic Foldamers with Iminodicarbonyl Linkers:  Their Stabilities and Application to a Chiral Photochromic System Using Retro [4 + 4] Cycloaddition. The Journal of Organic Chemistry 2006, 71 (21) , 8037-8044. https://doi.org/10.1021/jo0611317
    10. Hajime Abe,, Nozomi Masuda,, Minoru Waki, and, Masahiko Inouye. Regulation of Saccharide Binding with Basic Poly(ethynylpyridine)s by H+-Induced Helix Formation. Journal of the American Chemical Society 2005, 127 (46) , 16189-16196. https://doi.org/10.1021/ja054134u
    11. Bamidele Adisa and, David A. Bruce. Solvophobic and Steric Effects of Side Groups on Polymer Folding:  Molecular Modeling Studies of Amine-Functionalized m-Poly(phenyleneethynylene) Foldamers in Aqueous Solution. The Journal of Physical Chemistry B 2005, 109 (42) , 19952-19959. https://doi.org/10.1021/jp053607g
    12. Matthew T. Stone and, Jeffrey S. Moore. Supramolecular Chelation Based on Folding. Journal of the American Chemical Society 2005, 127 (16) , 5928-5935. https://doi.org/10.1021/ja050713n
    13. Hyuma Masu,, Masaki Sakai,, Keiki Kishikawa,, Makoto Yamamoto,, Kentaro Yamaguchi, and, Shigeo Kohmoto. Aromatic Foldamers with Iminodicarbonyl Linkers:  Their Structures and Optical Properties. The Journal of Organic Chemistry 2005, 70 (4) , 1423-1431. https://doi.org/10.1021/jo048233m
    14. Lihua Yuan,, Huaqiang Zeng,, Kazuhiro Yamato,, Adam R. Sanford,, Wen Feng,, Hanudatta S. Atreya,, Dinesh K. Sukumaran,, Thomas Szyperski, and, Bing Gong. Helical Aromatic Oligoamides:  Reliable, Readily Predictable Folding from the Combination of Rigidified Structural Motifs. Journal of the American Chemical Society 2004, 126 (50) , 16528-16537. https://doi.org/10.1021/ja046858w
    15. Jennifer M. Heemstra and, Jeffrey S. Moore. Enhanced Methylation Rate within a Foldable Molecular Receptor. The Journal of Organic Chemistry 2004, 69 (26) , 9234-9237. https://doi.org/10.1021/jo048506d
    16. Noritomo Kobayashi,, Shintaro Sasaki,, Masahiro Abe,, Shoutaro Watanabe,, Hiroki Fukumoto, and, Takakazu Yamamoto. Chain Distortion of m-Linked Aromatic Polymers:  Poly(m-phenylene) and Poly(m-pyridine). Macromolecules 2004, 37 (21) , 7986-7991. https://doi.org/10.1021/ma048923s
    17. Abdul-Malek S. Altamimi, Ahmed M. Alafeefy, Agnese Balode, Igor Vozny, Aleksandrs Pustenko, Mohey Eldin El Shikh, Fatmah A. S. Alasmary, Sherif A. Abdel-Gawad, Raivis Žalubovskis. Symmetric molecules with 1,4-triazole moieties as potent inhibitors of tumour-associated lactate dehydrogenase-A. Journal of Enzyme Inhibition and Medicinal Chemistry 2018, 33 (1) , 147-150. https://doi.org/10.1080/14756366.2017.1404593
    18. Sourav Bhowmick, Sourav Chakraborty, Subba R. Marri, J. N. Behera, Neeladri Das. Pyrazine-based donor tectons: synthesis, self-assembly and characterization. RSC Advances 2016, 6 (11) , 8992-9001. https://doi.org/10.1039/C5RA21484J
    19. Jee Seon Kim, Hae-Geun Jeon, Kyu-Sung Jeong. Modulation of helix stability of indolocarbazole–pyridine hybrid foldamers. Chemical Communications 2016, 52 (16) , 3406-3409. https://doi.org/10.1039/C6CC00045B
    20. Nozomi Saito. Homo-Double-Helix Formation of Ethynylhelicene Oligomers Possessing Various Side Chains. 2013, 11-28. https://doi.org/10.1007/978-4-431-54514-9_3
    21. Nicholas G. White, Paul D. Beer. A rotaxane host system containing integrated triazole C–H hydrogen bond donors for anion recognition. Organic & Biomolecular Chemistry 2013, 11 (8) , 1326. https://doi.org/10.1039/c2ob27229f
    22. Nicholas G. White, Sílvia Carvalho, Vítor Félix, Paul D. Beer. Anion binding in aqueous media by a tetra-triazolium macrocycle. Organic & Biomolecular Chemistry 2012, 10 (34) , 6951. https://doi.org/10.1039/c2ob25934f
    23. Iwao Okamoto, Masayuki Terashima, Hyuma Masu, Mayumi Nabeta, Kaori Ono, Nobuyoshi Morita, Kosuke Katagiri, Isao Azumaya, Osamu Tamura. Acid-induced conformational alteration of cis-preferential aromatic amides bearing N-methyl-N-(2-pyridyl) moiety. Tetrahedron 2011, 67 (44) , 8536-8543. https://doi.org/10.1016/j.tet.2011.08.085
    24. Yao-Rong Zheng, Ming Wang, Shiho Kobayashi, Peter J. Stang. Self-assembly of coordinative supramolecular polygons with open binding sites. Tetrahedron Letters 2011, 52 (17) , 2188-2191. https://doi.org/10.1016/j.tetlet.2010.11.119
    25. Ben-Bo Ni, Qifan Yan, Yuguo Ma, Dahui Zhao. Recent advances in arylene ethynylene folding systems: Toward functioning. Coordination Chemistry Reviews 2010, 254 (9-10) , 954-971. https://doi.org/10.1016/j.ccr.2010.02.004
    26. Christian Schafmeister, Stephen Habay. Building Block Approaches to Nonlinear and Linear Macromolecules. 2007, 19-1-19-35. https://doi.org/10.1201/9781420007848.ch19
    27. Jacek Gawronski, Magdalena Kaik, Marcin Kwit, Urszula Rychlewska. Solvent induced folding of conformationally bistable helical imide triads. Tetrahedron 2006, 62 (33) , 7866-7877. https://doi.org/10.1016/j.tet.2006.05.039
    28. Michio Goichi, Hiroaki Miyahara, Shinji Toyota. Construction of Strained Frameworks with 1,8-Anthrylene Units and Acetylene Linkers: Synthesis and Structures of Cyclic Trimers. Chemistry Letters 2006, 35 (8) , 920-921. https://doi.org/10.1246/cl.2006.920
    29. Michio Goichi, Shinji Toyota. Construction of Three-dimensional Framework with 1,8-Anthrylene and Butadiynylene Building Units: Synthesis and Properties of Cyclic Tetramers. Chemistry Letters 2006, 35 (6) , 684-685. https://doi.org/10.1246/cl.2006.684
    30. Shinji Toyota, Michio Goichi, Masashi Kotani, Makoto Takezaki. Chemistry of Anthracene–Acetylene Oligomers. II. Synthesis, Structure, and Properties of 1,8-Anthrylene–Ethynylene Cyclic Tetramers and Related Acyclic Oligomers. Bulletin of the Chemical Society of Japan 2005, 78 (12) , 2214-2227. https://doi.org/10.1246/bcsj.78.2214
    31. Nicholas H. Williams. 14  Bioinspired organic chemistry. Annual Reports Section "B" (Organic Chemistry) 2005, 101 , 352. https://doi.org/10.1039/b418980a

    Organic Letters

    Cite this: Org. Lett. 2004, 6, 6, 889–892
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol036376+
    Published February 21, 2004
    Copyright © 2004 American Chemical Society

    Article Views

    1314

    Altmetric

    -

    Citations

    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.