Highly Functionalized Dimeric Tetraethynylethenes and Expanded Radialenes: Strong Evidence for Macrocyclic Cross-Conjugation

A selection of dimeric tetraethynylethenes (TEEs) and perethynylated expanded radialenes, containing different donor/acceptor substitution patterns, have been prepared and fully characterized. The first X‐ray crystal structure of an expanded [6]radialene, with twelve peripheral 3,5‐di(tert‐butyl)phe...

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Published inChemistry : a European journal Vol. 7; no. 15; pp. 3263 - 3280
Main Authors Nielsen, Mogens Brøndsted, Schreiber, Martin, Baek, Yong Gu, Seiler, Paul, Lecomte, Steve, Boudon, Corinne, Tykwinski, Rik R., Gisselbrecht, Jean-Paul, Gramlich, Volker, Skinner, Philip J., Bosshard, Christian, Günter, Peter, Gross, Maurice, Diederich, François
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag GmbH 03.08.2001
WILEY‐VCH Verlag GmbH
Wiley
Subjects
alkynes
Chemistry
Chemistry, Multidisciplinary
conjugation
electrochemistry
expanded radialenes
nonlinear optics
Physical Sciences
Science & Technology
OPENING METATHESIS POLYMERIZATION
STRUCTURE-PROPERTY RELATIONSHIPS
electrochemistry
alkynes
expanded radialenes
OPTICAL 3RD-HARMONIC GENERATION
RODS
conjugation
ALL-CARBON
EXCITED-STATES
nonlinear optics
LIQUID-CRYSTAL POLYMERS
CHROMOPHORES
CHARGE SEPARATION
ELECTRONIC CHARACTERISTICS
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Abstract A selection of dimeric tetraethynylethenes (TEEs) and perethynylated expanded radialenes, containing different donor/acceptor substitution patterns, have been prepared and fully characterized. The first X‐ray crystal structure of an expanded [6]radialene, with twelve peripheral 3,5‐di(tert‐butyl)phenyl substituents, is presented. This macrocycle, the all‐carbon core of which is isomeric with fullerene C60, adopts a non‐planar, “chair‐like” conformation. Also a TEE dimer, carrying N,N‐dimethylaniline donor substituents, has been subjected to an X‐ray crystallographic analysis. The electronic properties were studied by UV/Vis spectroscopy and electrochemistry, providing fundamental insight into mechanisms of π‐electron delocalization in the acyclic and macrocyclic chromophores. Donor or donor–acceptor‐substituted dimeric TEE derivatives show very strong absorptions extending over the entire UV/Vis region; their longest wavelength absorption bands have high charge‐transfer character. Macrocyclic cross‐conjugation in the expanded radialenes becomes increasingly efficient with increasing donor–acceptor polarization. A dual, strongly solvent‐polarity‐dependent fluorescence was observed for a tetrakis(N,N‐dimethylaniline)‐substituted dimeric TEE; this interesting emission behavior is explained by the twisted intramolecular charge‐transfer (TICT) state model. Donor‐substituted expanded radialenes display huge resonance‐enhanced third‐order nonlinear optical coefficients. Expanded radialenes exhibit remarkable electronic properties owing to a considerable degree of macrocyclic cross‐conjugation. An expanded [6]radialene (see figure, middle, m = 3) with a central C60 core adopts a chair‐like conformation as depicted according to an X‐ray analysis.
AbstractList A selection of dimeric tetra-ethynylethenes (TEEs) and perethynylated expanded radialenes, containing different donor/acceptor substitution patterns, have been prepared and fully characterized. The first X-ray crystal structure of an expanded [6]radialene, with twelve peripheral 3,5-di(tert-butyl)phenyl substituents, is presented. This macrocycle, the all-carbon core of which is isomeric with fullerene C-60, adopts a non-planar, "chair-like" conformation. Also a TEE dimer, carrying NN-dimethylaniline donor substituents, has been subjected to an X-ray crystallo graphic analysis. The electronic properties were studied by UV/Vis spectroscopy and electrochemistry, providing fundamental insight into mechanisms of pi -electron delocalization in the acyclic and macrocyclic chromophores. Donor or donor-acceptor-substituted dimeric TEE derivatives show very strong absorptions extending over the entire UV/Vis region; their longest wavelength absorption bands have high charge-transfer character. Macrocyclic cross-conjugation in the expanded radialenes becomes increasingly efficient with increasing donor-acceptor polarization. A dual, strongly solvent-polarity-dependent fluorescence was observed for a tetrakis(NN-dimethylaniline)-substituted dimeric TEE; this interesting emission behavior is explained by the twisted intramolecular charge-transfer (TICT) state model. Donor-substituted expanded radialenes display huge resonance-enhanced third-order nonlinear optical coefficients.
A selection of dimeric tetraethynylethenes (TEEs) and perethynylated expanded radialenes, containing different donor/acceptor substitution patterns, have been prepared and fully characterized. The first X-ray crystal structure of an expanded [6]radialene, with twelve peripheral 3,5-di(tert-butyl)phenyl substituents, is presented. This macrocycle, the all-carbon core of which is isomeric with fullerene C60, adopts a non-planar, "chair-like" conformation. Also a TEE dimer, carrying N,N-dimethylaniline donor substituents, has been subjected to an X-ray crystallographic analysis. The electronic properties were studied by UV/Vis spectroscopy and electrochemistry, providing fundamental insight into mechanisms of pi-electron delocalization in the acyclic and macrocyclic chromophores. Donor or donor-acceptor-substituted dimeric TEE derivatives show very strong absorptions extending over the entire UV/Vis region; their longest wavelength absorption bands have high charge-transfer character. Macrocyclic cross-conjugation in the expanded radialenes becomes increasingly efficient with increasing donor-acceptor polarization. A dual, strongly solvent-polarity-dependent fluorescence was observed for a tetrakis(N,N-dimethylaniline)-substituted dimeric TEE; this interesting emission behavior is explained by the twisted intramolecular charge-transfer (TICT) state model. Donor-substituted expanded radialenes display huge resonance-enhanced third-order nonlinear optical coefficients.
A selection of dimeric tetraethynylethenes (TEEs) and perethynylated expanded radialenes, containing different donor/acceptor substitution patterns, have been prepared and fully characterized. The first X‐ray crystal structure of an expanded [6]radialene, with twelve peripheral 3,5‐di(tert‐butyl)phenyl substituents, is presented. This macrocycle, the all‐carbon core of which is isomeric with fullerene C60, adopts a non‐planar, “chair‐like” conformation. Also a TEE dimer, carrying N,N‐dimethylaniline donor substituents, has been subjected to an X‐ray crystallographic analysis. The electronic properties were studied by UV/Vis spectroscopy and electrochemistry, providing fundamental insight into mechanisms of π‐electron delocalization in the acyclic and macrocyclic chromophores. Donor or donor–acceptor‐substituted dimeric TEE derivatives show very strong absorptions extending over the entire UV/Vis region; their longest wavelength absorption bands have high charge‐transfer character. Macrocyclic cross‐conjugation in the expanded radialenes becomes increasingly efficient with increasing donor–acceptor polarization. A dual, strongly solvent‐polarity‐dependent fluorescence was observed for a tetrakis(N,N‐dimethylaniline)‐substituted dimeric TEE; this interesting emission behavior is explained by the twisted intramolecular charge‐transfer (TICT) state model. Donor‐substituted expanded radialenes display huge resonance‐enhanced third‐order nonlinear optical coefficients. Expanded radialenes exhibit remarkable electronic properties owing to a considerable degree of macrocyclic cross‐conjugation. An expanded [6]radialene (see figure, middle, m = 3) with a central C60 core adopts a chair‐like conformation as depicted according to an X‐ray analysis.
Author Skinner, Philip J.
Bosshard, Christian
Tykwinski, Rik R.
Gramlich, Volker
Nielsen, Mogens Brøndsted
Seiler, Paul
Gross, Maurice
Boudon, Corinne
Diederich, François
Gisselbrecht, Jean-Paul
Baek, Yong Gu
Günter, Peter
Schreiber, Martin
Lecomte, Steve
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  givenname: Martin
  surname: Schreiber
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  organization: Laboratorium für Organische Chemie, ETH-Zentrum Universitätstrasse 16, 8092 Zürich (Switzerland) Fax: (+41) 1 632 1109
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  givenname: Yong Gu
  surname: Baek
  fullname: Baek, Yong Gu
  organization: Laboratorium für Organische Chemie, ETH-Zentrum Universitätstrasse 16, 8092 Zürich (Switzerland) Fax: (+41) 1 632 1109
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  givenname: Paul
  surname: Seiler
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  organization: Laboratorium für Organische Chemie, ETH-Zentrum Universitätstrasse 16, 8092 Zürich (Switzerland) Fax: (+41) 1 632 1109
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  organization: Nonlinear Optics Laboratory Institute of Quantum Electronics ETH-Hönggerberg 8093 Zürich (Switzerland)
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  givenname: Corinne
  surname: Boudon
  fullname: Boudon, Corinne
  organization: Laboratoire d'Electrochimie et de Chimie Physique du Corps Solide UMR 7512, C.N.R.S, Université Louis Pasteur 4, rue Blaise Pascal 67 000 Strasbourg (France)
– sequence: 7
  givenname: Rik R.
  surname: Tykwinski
  fullname: Tykwinski, Rik R.
  organization: Department of Chemistry University of Alberta Edmonton, AB T6G 2G2 (Canada)
– sequence: 8
  givenname: Jean-Paul
  surname: Gisselbrecht
  fullname: Gisselbrecht, Jean-Paul
  organization: Laboratoire d'Electrochimie et de Chimie Physique du Corps Solide UMR 7512, C.N.R.S, Université Louis Pasteur 4, rue Blaise Pascal 67 000 Strasbourg (France)
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  givenname: Volker
  surname: Gramlich
  fullname: Gramlich, Volker
  organization: Laboratorium für Kristallographie, ETH-Zentrum Sonneggstrasse 5, 8092 Zürich (Switzerland)
– sequence: 10
  givenname: Philip J.
  surname: Skinner
  fullname: Skinner, Philip J.
  organization: Laboratorium für Organische Chemie, ETH-Zentrum Universitätstrasse 16, 8092 Zürich (Switzerland) Fax: (+41) 1 632 1109
– sequence: 11
  givenname: Christian
  surname: Bosshard
  fullname: Bosshard, Christian
  organization: Nonlinear Optics Laboratory Institute of Quantum Electronics ETH-Hönggerberg 8093 Zürich (Switzerland)
– sequence: 12
  givenname: Peter
  surname: Günter
  fullname: Günter, Peter
  organization: Nonlinear Optics Laboratory Institute of Quantum Electronics ETH-Hönggerberg 8093 Zürich (Switzerland)
– sequence: 13
  givenname: Maurice
  surname: Gross
  fullname: Gross, Maurice
  organization: Laboratoire d'Electrochimie et de Chimie Physique du Corps Solide UMR 7512, C.N.R.S, Université Louis Pasteur 4, rue Blaise Pascal 67 000 Strasbourg (France)
– sequence: 14
  givenname: François
  surname: Diederich
  fullname: Diederich, François
  email: diederich@org.chem.ethz.ch
  organization: Laboratorium für Organische Chemie, ETH-Zentrum Universitätstrasse 16, 8092 Zürich (Switzerland) Fax: (+41) 1 632 1109
BackLink https://www.ncbi.nlm.nih.gov/pubmed/11531112$$D View this record in MEDLINE/PubMed
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Issue 15
Keywords OPENING METATHESIS POLYMERIZATION
STRUCTURE-PROPERTY RELATIONSHIPS
electrochemistry
alkynes
expanded radialenes
OPTICAL 3RD-HARMONIC GENERATION
RODS
conjugation
ALL-CARBON
EXCITED-STATES
nonlinear optics
LIQUID-CRYSTAL POLYMERS
CHROMOPHORES
CHARGE SEPARATION
ELECTRONIC CHARACTERISTICS
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1999; 201
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1994; 27
1996; 79
1992 1992; 104 31
1997; 9
2001; 84
1968 1968; 80 7
1986; 108
1988 1988; 100 27
2001
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2000; 61
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1995 1995; 107 34
1984
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2000; 122
1980
1998; 10
1962; 84
1983; 24
1996; 8
1983; 109
1966; 4
1965; 77
1967; 89
1999 1999; 111 38
1991; 74
2000; 65
1999; 28
1989; 176
1982 1982; 94 21
1998
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1996
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1994 1994; 106 33
1993
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1995; 1
1999; 305
1995; 394
1995; 196
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1976; 98
1993; 58
1965; 87
1994; 369
1994; 169
1970; 92
1962; 27
1973; 29
1989; 173
1988; 110
2001; 2
1993 1993; 105 32
1994; 1
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2000 2000; 112 39
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Snippet A selection of dimeric tetraethynylethenes (TEEs) and perethynylated expanded radialenes, containing different donor/acceptor substitution patterns, have been...
A selection of dimeric tetra-ethynylethenes (TEEs) and perethynylated expanded radialenes, containing different donor/acceptor substitution patterns, have been...
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SubjectTerms alkynes
Chemistry
Chemistry, Multidisciplinary
conjugation
electrochemistry
expanded radialenes
nonlinear optics
Physical Sciences
Science & Technology
Title Highly Functionalized Dimeric Tetraethynylethenes and Expanded Radialenes: Strong Evidence for Macrocyclic Cross-Conjugation
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