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Title: Organogold oligomers: Exploiting iClick and aurophilic cluster formation to prepare solution stable Au 4 repeating units

Abstract

A novel synthetic method to create gold based metallo–oligomers/polymers via the combination of inorganic click (iClick) with intermolecular aurophilic interactions is demonstrated. Complexes [PEt 3Au] 4(μ-N 3C 2C 6H 5) (1) and [PPhMe 2Au] 43C 2C 6H 5) (2) and {[PEt 3Au] 4[(μ-N 3C 2) 2-9,9-dihexyl-9H-fluorene]} n (8) have been synthesized via iClick. The tetranuclear structures of 1 and 2, induced by aurophilic bonding, are confirmed in the solid state through single crystal X-ray diffraction experiments and in solution via variable temperature NMR spectroscopy. The extended 1D structure of 8 is constructed by aurophilic induced self-assembly. 1H DOSY NMR analysis reveals that the aurophilic bonds in 1, 2, and 8 are retained in the solution phase. The degree of polymerization within complex 8 is temperature and concentration dependent, as determined by 1H DOSY NMR. The complex 8 is a rare example of a solution stable higher ordered structure linked by aurophilic interactions.

Authors:
 [1];  [1];  [1];  [1];  [1]
  1. Univ. of Florida, Gainesville, FL (United States)
Publication Date:
Research Org.:
Univ. of Florida, Gainesville, FL (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1225601
Grant/Contract Number:  
SC0010510
Resource Type:
Journal Article: Accepted Manuscript
Journal Name:
Dalton Transactions
Additional Journal Information:
Journal Volume: 44; Journal Issue: 25; Journal ID: ISSN 1477-9226
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE

Citation Formats

Yang, Xi, Wang, Shanshan, Ghiviriga, Ion, Abboud, Khalil A., and Veige, Adam S. Organogold oligomers: Exploiting iClick and aurophilic cluster formation to prepare solution stable Au4 repeating units. United States: N. p., 2015. Web. doi:10.1039/C5DT00282F.
Yang, Xi, Wang, Shanshan, Ghiviriga, Ion, Abboud, Khalil A., & Veige, Adam S. Organogold oligomers: Exploiting iClick and aurophilic cluster formation to prepare solution stable Au4 repeating units. United States. doi:10.1039/C5DT00282F.
Yang, Xi, Wang, Shanshan, Ghiviriga, Ion, Abboud, Khalil A., and Veige, Adam S. Tue . "Organogold oligomers: Exploiting iClick and aurophilic cluster formation to prepare solution stable Au4 repeating units". United States. doi:10.1039/C5DT00282F. https://www.osti.gov/servlets/purl/1225601.
@article{osti_1225601,
title = {Organogold oligomers: Exploiting iClick and aurophilic cluster formation to prepare solution stable Au4 repeating units},
author = {Yang, Xi and Wang, Shanshan and Ghiviriga, Ion and Abboud, Khalil A. and Veige, Adam S.},
abstractNote = {A novel synthetic method to create gold based metallo–oligomers/polymers via the combination of inorganic click (iClick) with intermolecular aurophilic interactions is demonstrated. Complexes [PEt3Au]4(μ-N3C2C6H5) (1) and [PPhMe2Au]43C2C6H5) (2) and {[PEt3Au]4[(μ-N3C2)2-9,9-dihexyl-9H-fluorene]}n (8) have been synthesized via iClick. The tetranuclear structures of 1 and 2, induced by aurophilic bonding, are confirmed in the solid state through single crystal X-ray diffraction experiments and in solution via variable temperature NMR spectroscopy. The extended 1D structure of 8 is constructed by aurophilic induced self-assembly. 1H DOSY NMR analysis reveals that the aurophilic bonds in 1, 2, and 8 are retained in the solution phase. The degree of polymerization within complex 8 is temperature and concentration dependent, as determined by 1H DOSY NMR. The complex 8 is a rare example of a solution stable higher ordered structure linked by aurophilic interactions.},
doi = {10.1039/C5DT00282F},
journal = {Dalton Transactions},
issn = {1477-9226},
number = 25,
volume = 44,
place = {United States},
year = {2015},
month = {5}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

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Cited by: 7 works
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Figures / Tables:

Scheme 1 Scheme 1: iClick reactions.

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Works referenced in this record:

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    The “Click” Reaction Involving Metal Azides, Metal Alkynes, or Both: An Exploration into Multimetal Structures
    journal, February 2013

    • Casarrubios, Luis; de la Torre, María C.; Sierra, Miguel A.
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    • DOI: 10.1002/chem.201204596

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    • DOI: 10.1002/chem.201302502

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    • DOI: 10.1002/marc.200800089

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    • Nagao, Yu; Takasu, Akinori
    • Journal of Polymer Science Part A: Polymer Chemistry, Vol. 48, Issue 19
    • DOI: 10.1002/pola.24206

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    • White-Morris, Rochelle L.; Stender, Matthias; Tinti, Dino S.
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    • DOI: 10.1021/ic0206948

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    • Assefa, Zerihun; Omary, Mohammad A.; McBurnett, Brian G.
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    • DOI: 10.1021/ic025784r

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    • Dau, Thuy Minh; Chen, Yi-An; Karttunen, Antti J.
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    • DOI: 10.1021/ic501470v

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    • Inorganic Chemistry, Vol. 36, Issue 11
    • DOI: 10.1021/ic9607245

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    journal, October 1984

    • Chen, Hang Chang; Chen, Shaw Horng
    • The Journal of Physical Chemistry, Vol. 88, Issue 21
    • DOI: 10.1021/j150665a063

    Oligomerization of Au(CN) 2 - and Ag(CN) 2 - Ions in Solution via Ground-State Aurophilic and Argentophilic Bonding
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    • Rawashdeh-Omary, Manal A.; Omary, Mohammad A.; Patterson, Howard H.
    • Journal of the American Chemical Society, Vol. 122, Issue 42
    • DOI: 10.1021/ja001545w

    Excited-State Interactions for [Au(CN) 2 - ] n and [Ag(CN) 2 - ] n Oligomers in Solution. Formation of Luminescent Gold−Gold Bonded Excimers and Exciplexes
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    • Rawashdeh-Omary, Manal A.; Omary, Mohammad A.; Patterson, Howard H.
    • Journal of the American Chemical Society, Vol. 123, Issue 45
    • DOI: 10.1021/ja011176j

    Crystal Chemistry of the Gold (I) Trimer, Au 3 (NC 5 H 4 ) 3 :  Formation of Hourglass Figures and Self-Association through Aurophilic Attraction
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    • Hayashi, Akari; Olmstead, Marilyn M.; Attar, Saeed
    • Journal of the American Chemical Society, Vol. 124, Issue 20
    • DOI: 10.1021/ja012416y

    Luminescence Tribochromism and Bright Emission in Gold(I) Thiouracilate Complexes
    journal, July 2003

    • Lee, Young-A; Eisenberg, Richard
    • Journal of the American Chemical Society, Vol. 125, Issue 26
    • DOI: 10.1021/ja034560k

    Ultrathin Gold Nanowires Can Be Obtained by Reducing Polymeric Strands of Oleylamine−AuCl Complexes Formed via Aurophilic Interaction
    journal, July 2008

    • Lu, Xianmao; Yavuz, Mustafa S.; Tuan, Hsing-Yu
    • Journal of the American Chemical Society, Vol. 130, Issue 28
    • DOI: 10.1021/ja803343m

    Peptidotriazoles on Solid Phase  [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides
    journal, May 2002

    • Tornøe, Christian W.; Christensen, Caspar; Meldal, Morten
    • The Journal of Organic Chemistry, Vol. 67, Issue 9, p. 3057-3064
    • DOI: 10.1021/jo011148j

    Carbon−Gold Bond Formation through [3 + 2] Cycloaddition Reactions of Gold(I) Azides and Terminal Alkynes
    journal, January 2007

    • Partyka, David V.; Updegraff, James B.; Zeller, Matthias
    • Organometallics, Vol. 26, Issue 1
    • DOI: 10.1021/om0607200

    [3+2] Cycloadditions of Molybdenum(II) Azide Complexes with Nitriles and an Alkyne
    journal, October 2010

    • Liu, Fu-Chen; Lin, Yu-Liang; Yang, Pei-Shan
    • Organometallics, Vol. 29, Issue 19
    • DOI: 10.1021/om1007083

    Toward Permetalated Alkyne/Azide 3 + 2 or “Click” Cycloadducts
    journal, July 2012

    • Clough, Melissa C.; Zeits, Paul D.; Bhuvanesh, Nattamai
    • Organometallics, Vol. 31, Issue 15
    • DOI: 10.1021/om300542a

    Copper-Catalyzed Huisgen [3 + 2] Cycloaddition of Gold(I) Alkynyls with Benzyl Azide. Syntheses, Structures, and Optical Properties
    journal, November 2009

    • Partyka, David V.; Gao, Lei; Teets, Thomas S.
    • Organometallics, Vol. 28, Issue 21
    • DOI: 10.1021/om9005774

    Rigid-Rod Polymers and Model Compounds with Gold(I) Centers Bridged by Diisocyanides and Diacetylides
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