Reactivity of TCNE and TCNQ derivatives of quinonoid zwitterions with Cu(I)

Thomas Kauf; Vitor Rosa; Christophe Fliedel; Roberto Pattacini; Naina Deibel; Maria Teresa Avilés; Biprajit Sarkar; Pierre Braunstein

doi:10.1039/c4dt03956d

Reactivity of TCNE and TCNQ derivatives of quinonoid zwitterions with Cu(I)

Thomas Kauf, Vitor Rosa, Christophe Fliedel, Roberto Pattacini, Naina Deibel, Maria Teresa Avilés, Biprajit Sarkar, Pierre Braunstein

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

The reactions of TCNE- and TCNQ-functionalized (TCNE: tetracyanoethylene and TCNQ: 7,7′,8,8′-tetracyanoquinodimethane) zwitterionic benzoquinonemonoimines with a Cu(i)-BIAN complex (BIAN = bis(o,o′-bisisopropylphenyl)acenaphthenequinonediimine) have been investigated and found to follow a diversity of interesting patterns. The complexes [Cu(BIAN)(NCMe)(L2)]BF₄ (2) and [Cu(BIAN)(L2)₂]BF₄ (4) were obtained by reacting [Cu(BIAN)(NCMe)₂]BF₄ (1) with one and two equivalents of L2, respectively. Following similar procedures, the complexes [Cu(BIAN)(NCMe)(L3)]BF₄ (6) and [Cu(BIAN)(L3)₂]BF₄ (7) were obtained by reaction of 1 with L3. The reaction of 2 with 0.5 equiv. of 4,4′-bipyridine afforded [{Cu(BIAN)(L2)}₂(μ-4,4′-bipyridine)](BF₄)₂ (3). The complexes were characterized by multinuclear NMR, IR and UV-Vis spectroscopic techniques, mass spectrometry, cyclic voltammetry and elemental analysis. The molecular structures of complexes 3·4CH₂Cl₂ and 4·CH₂Cl₂ were determined by single crystal X-ray diffraction. An unexpected coordination polymer [Cu(L2^-)₂]_∞ (5) was also structurally characterized, which contains Cu(ii) centres chelated by two N,O-bound ligands resulting from the monodeprotonation of L2.

Original language	English
Pages (from-to)	5441-5450
Number of pages	10
Journal	Dalton Transactions
Volume	44
Issue number	12
DOIs	https://doi.org/10.1039/c4dt03956d
Publication status	Published - 28 Mar 2015

Keywords

METAL-COMPLEXES
BENZOQUINONEMONOIMINE DERIVATIVES
LIGANDS
CHEMISTRY
COORDINATION
MAGNETS
CYCLOADDITION
SURFACES
DIPOLE
PHASE

Access to Document

10.1039/c4dt03956dLicence: Unspecified

Cite this

@article{ad5e81bbc5ef463d98cf4003192db4e4,

title = "Reactivity of TCNE and TCNQ derivatives of quinonoid zwitterions with Cu(I)",

abstract = "The reactions of TCNE- and TCNQ-functionalized (TCNE: tetracyanoethylene and TCNQ: 7,7′,8,8′-tetracyanoquinodimethane) zwitterionic benzoquinonemonoimines with a Cu(i)-BIAN complex (BIAN = bis(o,o′-bisisopropylphenyl)acenaphthenequinonediimine) have been investigated and found to follow a diversity of interesting patterns. The complexes [Cu(BIAN)(NCMe)(L2)]BF4 (2) and [Cu(BIAN)(L2)2]BF4 (4) were obtained by reacting [Cu(BIAN)(NCMe)2]BF4 (1) with one and two equivalents of L2, respectively. Following similar procedures, the complexes [Cu(BIAN)(NCMe)(L3)]BF4 (6) and [Cu(BIAN)(L3)2]BF4 (7) were obtained by reaction of 1 with L3. The reaction of 2 with 0.5 equiv. of 4,4′-bipyridine afforded [{Cu(BIAN)(L2)}2(μ-4,4′-bipyridine)](BF4)2 (3). The complexes were characterized by multinuclear NMR, IR and UV-Vis spectroscopic techniques, mass spectrometry, cyclic voltammetry and elemental analysis. The molecular structures of complexes 3·4CH2Cl2 and 4·CH2Cl2 were determined by single crystal X-ray diffraction. An unexpected coordination polymer [Cu(L2-)2]∞ (5) was also structurally characterized, which contains Cu(ii) centres chelated by two N,O-bound ligands resulting from the monodeprotonation of L2.",

keywords = "METAL-COMPLEXES , BENZOQUINONEMONOIMINE DERIVATIVES , LIGANDS , CHEMISTRY , COORDINATION , MAGNETS , CYCLOADDITION , SURFACES , DIPOLE , PHASE",

author = "Thomas Kauf and Vitor Rosa and Christophe Fliedel and Roberto Pattacini and Naina Deibel and Avil{\'e}s, {Maria Teresa} and Biprajit Sarkar and Pierre Braunstein",

note = "Sem PDF. We are grateful to the Universite de Strasbourg and the ANR (07-BLANC-0274-04) for support, the Centre National de la Recherche Scientifique (CNRS) for a post-doctoral grant to T. K. and the Fundacao para a Ciencia e a Tecnologia (FCT) (fellowships SFRH/BPD/73253/2010 to C.F. and SFRH/BPD/44262/2008 to V.R.) for funding. We thank the Service de Radiocristallographie, Institut de Chimie (UMR 7177 CNRS-UdS) for the X-ray diffraction studies.",

year = "2015",

month = mar,

day = "28",

doi = "10.1039/c4dt03956d",

language = "English",

volume = "44",

pages = "5441--5450",

journal = "Dalton Transactions",

issn = "1477-9226",

publisher = "RSC - Royal Society of Chemistry",

number = "12",

}

TY - JOUR

T1 - Reactivity of TCNE and TCNQ derivatives of quinonoid zwitterions with Cu(I)

AU - Kauf, Thomas

AU - Rosa, Vitor

AU - Fliedel, Christophe

AU - Pattacini, Roberto

AU - Deibel, Naina

AU - Avilés, Maria Teresa

AU - Sarkar, Biprajit

AU - Braunstein, Pierre

N1 - Sem PDF. We are grateful to the Universite de Strasbourg and the ANR (07-BLANC-0274-04) for support, the Centre National de la Recherche Scientifique (CNRS) for a post-doctoral grant to T. K. and the Fundacao para a Ciencia e a Tecnologia (FCT) (fellowships SFRH/BPD/73253/2010 to C.F. and SFRH/BPD/44262/2008 to V.R.) for funding. We thank the Service de Radiocristallographie, Institut de Chimie (UMR 7177 CNRS-UdS) for the X-ray diffraction studies.

PY - 2015/3/28

Y1 - 2015/3/28

N2 - The reactions of TCNE- and TCNQ-functionalized (TCNE: tetracyanoethylene and TCNQ: 7,7′,8,8′-tetracyanoquinodimethane) zwitterionic benzoquinonemonoimines with a Cu(i)-BIAN complex (BIAN = bis(o,o′-bisisopropylphenyl)acenaphthenequinonediimine) have been investigated and found to follow a diversity of interesting patterns. The complexes [Cu(BIAN)(NCMe)(L2)]BF4 (2) and [Cu(BIAN)(L2)2]BF4 (4) were obtained by reacting [Cu(BIAN)(NCMe)2]BF4 (1) with one and two equivalents of L2, respectively. Following similar procedures, the complexes [Cu(BIAN)(NCMe)(L3)]BF4 (6) and [Cu(BIAN)(L3)2]BF4 (7) were obtained by reaction of 1 with L3. The reaction of 2 with 0.5 equiv. of 4,4′-bipyridine afforded [{Cu(BIAN)(L2)}2(μ-4,4′-bipyridine)](BF4)2 (3). The complexes were characterized by multinuclear NMR, IR and UV-Vis spectroscopic techniques, mass spectrometry, cyclic voltammetry and elemental analysis. The molecular structures of complexes 3·4CH2Cl2 and 4·CH2Cl2 were determined by single crystal X-ray diffraction. An unexpected coordination polymer [Cu(L2-)2]∞ (5) was also structurally characterized, which contains Cu(ii) centres chelated by two N,O-bound ligands resulting from the monodeprotonation of L2.

AB - The reactions of TCNE- and TCNQ-functionalized (TCNE: tetracyanoethylene and TCNQ: 7,7′,8,8′-tetracyanoquinodimethane) zwitterionic benzoquinonemonoimines with a Cu(i)-BIAN complex (BIAN = bis(o,o′-bisisopropylphenyl)acenaphthenequinonediimine) have been investigated and found to follow a diversity of interesting patterns. The complexes [Cu(BIAN)(NCMe)(L2)]BF4 (2) and [Cu(BIAN)(L2)2]BF4 (4) were obtained by reacting [Cu(BIAN)(NCMe)2]BF4 (1) with one and two equivalents of L2, respectively. Following similar procedures, the complexes [Cu(BIAN)(NCMe)(L3)]BF4 (6) and [Cu(BIAN)(L3)2]BF4 (7) were obtained by reaction of 1 with L3. The reaction of 2 with 0.5 equiv. of 4,4′-bipyridine afforded [{Cu(BIAN)(L2)}2(μ-4,4′-bipyridine)](BF4)2 (3). The complexes were characterized by multinuclear NMR, IR and UV-Vis spectroscopic techniques, mass spectrometry, cyclic voltammetry and elemental analysis. The molecular structures of complexes 3·4CH2Cl2 and 4·CH2Cl2 were determined by single crystal X-ray diffraction. An unexpected coordination polymer [Cu(L2-)2]∞ (5) was also structurally characterized, which contains Cu(ii) centres chelated by two N,O-bound ligands resulting from the monodeprotonation of L2.

KW - METAL-COMPLEXES

KW - BENZOQUINONEMONOIMINE DERIVATIVES

KW - LIGANDS

KW - CHEMISTRY

KW - COORDINATION

KW - MAGNETS

KW - CYCLOADDITION

KW - SURFACES

KW - DIPOLE

KW - PHASE

UR - http://www.scopus.com/inward/record.url?scp=84924767476&partnerID=8YFLogxK

U2 - 10.1039/c4dt03956d

DO - 10.1039/c4dt03956d

M3 - Article

C2 - 25689916

AN - SCOPUS:84924767476

SN - 1477-9226

VL - 44

SP - 5441

EP - 5450

JO - Dalton Transactions

JF - Dalton Transactions

IS - 12

ER -

Reactivity of TCNE and TCNQ derivatives of quinonoid zwitterions with Cu(I)

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this