DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Expanding iClick to group 9 metals

Abstract

In this study, the iClick (inorganic click) reactions between gold-acetylides and group 9 transition metal-azide complexes are presented. Complexes [Rh(CO)(PPh3)2][PPh3Au](μ-N3C2C6H4NO2) (3), {[Rh(CO)(PPh3)][PPh3Au](μ-N3C2C6H4NO2)}2 (4), and [(CO)(PPh3)2IrAuPPh3](μ-N3C2C6H4NO2) (6) have been synthesized via M-azide/M-acetylide cycloaddition reactions between PPh3Au(Ctriple bond; length of mdashCC6H4NO2) (2) and either Rh(CO)(PPh3)2N3 (1), or Ir(CO)(PPh3)2N3 (5). Complexes 3, 4, and 6 have been characterized by a combination of NMR spectroscopies, crystallography and combustion analysis.

Authors:
 [1];  [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)
OSTI Identifier:
1225602
Alternate Identifier(s):
OSTI ID: 1373338
Grant/Contract Number:  
SC0010510
Resource Type:
Accepted Manuscript
Journal Name:
Polyhedron
Additional Journal Information:
Journal Name: Polyhedron; Journal ID: ISSN 0277-5387
Publisher:
Elsevier
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; iClick; azide-alkyne cycloaddition; rhodium; iridium; heterobimetallic

Citation Formats

Beto, Christopher C., Yang, Xi, Powers, Andrew R., Ghiviriga, Ion, Abboud, Khalil A., and Veige, Adam S. Expanding iClick to group 9 metals. United States: N. p., 2015. Web. doi:10.1016/j.poly.2015.08.032.
Beto, Christopher C., Yang, Xi, Powers, Andrew R., Ghiviriga, Ion, Abboud, Khalil A., & Veige, Adam S. Expanding iClick to group 9 metals. United States. https://doi.org/10.1016/j.poly.2015.08.032
Beto, Christopher C., Yang, Xi, Powers, Andrew R., Ghiviriga, Ion, Abboud, Khalil A., and Veige, Adam S. Tue . "Expanding iClick to group 9 metals". United States. https://doi.org/10.1016/j.poly.2015.08.032. https://www.osti.gov/servlets/purl/1225602.
@article{osti_1225602,
title = {Expanding iClick to group 9 metals},
author = {Beto, Christopher C. and Yang, Xi and Powers, Andrew R. and Ghiviriga, Ion and Abboud, Khalil A. and Veige, Adam S.},
abstractNote = {In this study, the iClick (inorganic click) reactions between gold-acetylides and group 9 transition metal-azide complexes are presented. Complexes [Rh(CO)(PPh3)2][PPh3Au](μ-N3C2C6H4NO2) (3), {[Rh(CO)(PPh3)][PPh3Au](μ-N3C2C6H4NO2)}2 (4), and [(CO)(PPh3)2IrAuPPh3](μ-N3C2C6H4NO2) (6) have been synthesized via M-azide/M-acetylide cycloaddition reactions between PPh3Au(Ctriple bond; length of mdashCC6H4NO2) (2) and either Rh(CO)(PPh3)2N3 (1), or Ir(CO)(PPh3)2N3 (5). Complexes 3, 4, and 6 have been characterized by a combination of NMR spectroscopies, crystallography and combustion analysis.},
doi = {10.1016/j.poly.2015.08.032},
journal = {Polyhedron},
number = ,
volume = ,
place = {United States},
year = {Tue Sep 01 00:00:00 EDT 2015},
month = {Tue Sep 01 00:00:00 EDT 2015}
}

Journal Article:

Citation Metrics:
Cited by: 12 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Metallopolymers: New Multifunctional Materials
journal, November 2007


Functional soft materials from metallopolymers and metallosupramolecular polymers
journal, February 2011

  • Whittell, George R.; Hager, Martin D.; Schubert, Ulrich S.
  • Nature Materials, Vol. 10, Issue 3
  • DOI: 10.1038/nmat2966

Synthesis and electropolymerisation of 1,1′-bis(5-oligothienyl)ferrocenes: poly(oligothiophene–ferrocene)-modified electrodes
journal, January 1999


Electropolymerization of Oligothienylferrocene Complexes:  Spectroscopic and Electrochemical Characterization
journal, October 1999

  • Zhu, Yongbao; Wolf, Michael O.
  • Chemistry of Materials, Vol. 11, Issue 10
  • DOI: 10.1021/cm990391k

A conjugated polymer/redox polymer hybrid with electronic communication between metal centres
journal, January 1997

  • Cameron, Colin G.; Pickup, Peter G.
  • Chemical Communications, Issue 3
  • DOI: 10.1039/a607671h

Synthesis of Poly(biphenylene ruthenacyclopentatrienylene), a New Organometallic Conducting Polymer with Ferromagnetic Interaction in Its Reduced State
journal, October 2003

  • Kurashina, Masashi; Murata, Masaki; Watanabe, Tokuko
  • Journal of the American Chemical Society, Vol. 125, Issue 41
  • DOI: 10.1021/ja036934f

Organometallic conducting polymers synthesized by metallacycling polymerization
journal, July 2003

  • Nishihara, Hiroshi; Kurashina, Masashi; Murata, Masaki
  • Macromolecular Symposia, Vol. 196, Issue 1
  • DOI: 10.1002/masy.200390168

Polythiophene Hybrids of Transition-Metal Bis(salicylidenimine)s:  Correlation between Structure and Electronic Properties
journal, September 1999

  • Kingsborough, Richard P.; Swager, Timothy M.
  • Journal of the American Chemical Society, Vol. 121, Issue 38
  • DOI: 10.1021/ja991285m

Electroactivity Enhancement by Redox Matching in Cobalt Salen-Based Conducting Polymers
journal, October 1998


Polyterthiophene π-conjugated by organomolybdenum complex (II): electropolymerization of erythro-[(η5-C5H5)2Mo2(O)2(μ-O){μ-η2:η2-C(Ph)C[C4HS(C4H3S-2)2-2,5]}]
journal, August 2000


Polyterthiophene appended by transition-metal cluster: electropolymerization of 3′-[CCo3(CO)9]-5,2′:5′,2″-terthiophene
journal, August 1999


Electrogenerated poly(thiophenes) derivatized by bipyridine ligands and metal complexes
journal, January 2004

  • Jousselme, Bruno; Blanchard, Philippe; Oçafrain, Maïtena
  • J. Mater. Chem., Vol. 14, Issue 3
  • DOI: 10.1039/B313291A

Electrochemical investigation of novel polymerizable thiophene/ferrocene conjugates
journal, March 1992


Conductivity In Redox Modified Conducting Polymers. 2. Enhanced Redox Conductivity in Ferrocene-Substituted Polypyrroles and Polythiophenes
journal, December 1995

  • Zotti, Gianni; Zecchin, Sandro; Schiavon, Gilberto
  • Chemistry of Materials, Vol. 7, Issue 12
  • DOI: 10.1021/cm00060a019

Self-assembly and electropolymerization of pyrrole- and bithiophene-n-hexyl-ferrocene molecules on ITO electrodes
journal, January 1997


Electrogenerated conjugated polymers incorporating a ferrocene-derivatized-(3,4-ethylenedioxythiophene)
journal, March 2004

  • Brisset, Hugues; Navarro, Aude-Emmanuelle; Moustrou, Corinne
  • Electrochemistry Communications, Vol. 6, Issue 3
  • DOI: 10.1016/j.elecom.2003.12.010

A Novel Polymeric Metallomacrocycle Sensor Capable of Dual-Ion Cocomplexation
journal, January 1998

  • Reddinger, Jerry L.; Reynolds, John R.
  • Chemistry of Materials, Vol. 10, Issue 1
  • DOI: 10.1021/cm9705000

Electropolymerisation dynamics of a highly conducting metallopolymer: poly-[Os(4′-(5-(2,2′-bithienyl))-2,2′:6′,2″-terpyridine)2]2+
journal, February 2004


Conducting Polymers Containing In-Chain Metal Centers: Homogeneous Charge Transport through a Quaterthienyl-Bridged {Os(tpy) 2 } Polymer
journal, September 2003

  • Hjelm, Johan; Handel, Robyn W.; Hagfeldt, Anders
  • The Journal of Physical Chemistry B, Vol. 107, Issue 38
  • DOI: 10.1021/jp035139l

A rod-like polymer containing {Ru(terpy)2} units prepared by electrochemical coupling of pendant thienyl moieties
journal, January 2002

  • Hjelm, Johan; Constable, Edwin C.; Figgemeier, Egbert
  • Chemical Communications, Issue 3
  • DOI: 10.1039/b110479a

Charge Transfer and Delocalization in Conjugated (Ferrocenylethynyl)oligothiophene Complexes
journal, October 2000

  • Zhu, Yongbao; Wolf, Michael O.
  • Journal of the American Chemical Society, Vol. 122, Issue 41
  • DOI: 10.1021/ja0008564

Polyisobutylene-block-Poly(ethylene oxide) for Robust Templating of Highly Ordered Mesoporous Materials
journal, April 2005

  • Groenewolt, M.; Brezesinski, T.; Schlaad, H.
  • Advanced Materials, Vol. 17, Issue 9, p. 1158-1162
  • DOI: 10.1002/adma.200401549

Liquid crystalline main-chain polymers containing the ferrocene unit as a side group
journal, October 1996


Redox Properties of Hepta(1,1′-dihexylferrocenylene)
journal, January 1997


Radical Ion States of Platinum Acetylide Oligomers
journal, September 2007

  • Cardolaccia, Thomas; Funston, Alison M.; Kose, M. Erkan
  • The Journal of Physical Chemistry B, Vol. 111, Issue 37
  • DOI: 10.1021/jp0737552

Photophysics of Diplatinum Polyynediyl Oligomers: Chain Length Dependence of the Triplet State in sp Carbon Chains
journal, September 2007

  • Farley, Richard T.; Zheng, Qinglin; Gladysz, John A.
  • Inorganic Chemistry, Vol. 47, Issue 8
  • DOI: 10.1021/ic701220t

Synthesis of Monodisperse Platinum Acetylide Oligomers End-Capped with Naphthalene Diimide Units
journal, June 2009

  • Keller, Julia M.; Schanze, Kirk S.
  • Organometallics, Vol. 28, Issue 14
  • DOI: 10.1021/om900195p

Optimizing Simultaneous Two-Photon Absorption and Transient Triplet−Triplet Absorption in Platinum Acetylide Chromophores
journal, June 2010

  • Kim, Kye-Young; Shelton, Abigail H.; Drobizhev, Mikhail
  • The Journal of Physical Chemistry A, Vol. 114, Issue 26
  • DOI: 10.1021/jp1005567

Low-Band-Gap Platinum Acetylide Polymers as Active Materials for Organic Solar Cells
journal, January 2009

  • Mei, Jianguo; Ogawa, Katsu; Kim, Young-Gi
  • ACS Applied Materials & Interfaces, Vol. 1, Issue 1
  • DOI: 10.1021/am800104k

Hyperbranched Conjugated Polyelectrolyte Bilayers for Solar-Cell Applications
journal, July 2007

  • Taranekar, Prasad; Qiao, Qiquan; Jiang, Hui
  • Journal of the American Chemical Society, Vol. 129, Issue 29
  • DOI: 10.1021/ja073216a

A Platinum Acetylide Polymer with Sterically Demanding Substituents:  Effect of Aggregation on the Triplet Excited State
journal, April 2005

  • Zhao, Xiaoming; Cardolaccia, Thomas; Farley, Richard T.
  • Inorganic Chemistry, Vol. 44, Issue 8
  • DOI: 10.1021/ic048961s

1,3-Dipolar cycloaddition between a metal–azide (Ph3PAuN3) and a metal–acetylide (Ph3PAuCCPh): an inorganic version of a click reaction
journal, January 2011

  • Del Castillo, Trevor J.; Sarkar, Soumya; Abboud, Khalil A.
  • Dalton Transactions, Vol. 40, Issue 32
  • DOI: 10.1039/c1dt10787a

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

A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes
journal, July 2002


Organogold oligomers: exploiting iClick and aurophilic cluster formation to prepare solution stable Au 4 repeating units
journal, January 2015

  • Yang, Xi; Wang, Shanshan; Ghiviriga, Ion
  • Dalton Transactions, Vol. 44, Issue 25
  • DOI: 10.1039/C5DT00282F

Direct Evidence of a Dinuclear Copper Intermediate in Cu(I)-Catalyzed Azide-Alkyne Cycloadditions
journal, April 2013


Bildung von Isocyanato-Komplexen aus komplexen Metallaziden und Kohlenmonoxid
journal, June 1969

  • Beck, Wolfgang; Fehlhammer, Wolf Peter; Pöllmann, Peter
  • Chemische Berichte, Vol. 102, Issue 6
  • DOI: 10.1002/cber.19691020623

Zur Reaktoin von Azido-Metallverbindungen: Tetrazolato-Metallkomplexe
journal, November 1969

  • Beck, Wolfgang; Fehlhammer, Wolf Peter; Bock, Henning
  • Chemische Berichte, Vol. 102, Issue 11
  • DOI: 10.1002/cber.19691021105

A simple synthetic route to d 8 complexes of rhodium and iridium. An electronegativity scale for anionic ligands
journal, January 1971

  • Vaska, L.; Peone, J.
  • Journal of the Chemical Society D: Chemical Communications, Issue 9
  • DOI: 10.1039/c29710000418

Nuclearity control in gold dithiocarboxylato compounds
journal, January 2010

  • Gallego, M. Luz; Guijarro, Alejandro; Castillo, Oscar
  • CrystEngComm, Vol. 12, Issue 8
  • DOI: 10.1039/c001150a

Inorganic click (iClick) synthesis of heterotrinuclear PtII/AuI2 complexes
journal, January 2013

  • Powers, Andrew R.; Yang, Xi; Del Castillo, Trevor J.
  • Dalton Transactions, Vol. 42, Issue 42
  • DOI: 10.1039/c3dt52105b

Binding of lead(II), antimony(III), and other isoelectronic main-group ions to iridium in the metallomacrocycle Ir2(CO)2Cl2{.mu.-(Ph2PCH2)2AsPh}2
journal, February 1991

  • Balch, Alan L.; Catalano, Vincent J.; Chatfield, Mark A.
  • Journal of the American Chemical Society, Vol. 113, Issue 4
  • DOI: 10.1021/ja00004a027

Ligation-induced changes in metal-metal bonding in luminescent binuclear complexes containing gold(I) and iridium(I)
journal, March 1991

  • Balch, Alan L.; Catalano, Vincent J.
  • Inorganic Chemistry, Vol. 30, Issue 6
  • DOI: 10.1021/ic00006a027

Reactions involving chelate ring opening or metal ion relocation in the formation of luminescent complexes containing both gold and iridium
journal, October 1990

  • Balch, Alan L.; Catalano, Vincent J.; Noll, Bruce C.
  • Journal of the American Chemical Society, Vol. 112, Issue 21
  • DOI: 10.1021/ja00177a017

Chelate ring opening and metal ion relocation leading to the formation of a luminescent gold(I)-iridium(I)-gold(I) chain complex
journal, February 1990

  • Balch, Alan L.; Catalano, Vincent J.; Olmstead, Marilyn M.
  • Journal of the American Chemical Society, Vol. 112, Issue 5
  • DOI: 10.1021/ja00161a062

Synthesis and characterization of the novel gold-iridium cluster [IrAu4(H)2(PPh3)6]BF4
journal, July 1985

  • Casalnuovo, Albert L.; Casalnuovo, Joseph A.; Nilsson, Per V.
  • Inorganic Chemistry, Vol. 24, Issue 16
  • DOI: 10.1021/ic00210a018

Synthesis and characterization of cationic gold-iridium clusters. Structure of [IrAu2(H)(PPh3)4NO3]BF4
journal, January 1985

  • Casalnuovo, A. L.; Laska, T.; Nilsson, P. V.
  • Inorganic Chemistry, Vol. 24, Issue 2
  • DOI: 10.1021/ic00196a013

Synthesis and x-ray crystal structure of [(dppe)2IrAuPPh3](BF4)2
journal, January 1985

  • Casalnuovo, A. L.; Laska, T.; Nilsson, P. V.
  • Inorganic Chemistry, Vol. 24, Issue 2
  • DOI: 10.1021/ic00196a024

Reaction of Au(NO3)PPh3 with cationic polyhydride cluster complexes of iridium(III). Structures of [AuIr3H6(NO3)(dppe)3]BF4 and [Au3Ir(NO3)(PPh3)5]PF6
journal, September 1983

  • Casalnuovo, A. L.; Pignolet, L. H.; Van der Velden, J. W. A.
  • Journal of the American Chemical Society, Vol. 105, Issue 18
  • DOI: 10.1021/ja00356a062

OLEX2 : a complete structure solution, refinement and analysis program
journal, January 2009

  • Dolomanov, Oleg V.; Bourhis, Luc J.; Gildea, Richard J.
  • Journal of Applied Crystallography, Vol. 42, Issue 2
  • DOI: 10.1107/S0021889808042726

Works referencing / citing this record: