Synthesis and crystal structure of an acetylenic ferrocenyl substituted phosphaalkene

Dominique Miesel, Marcus Korb, Alexander Hildebrandt, Heinrich Lang

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

(E)-(5,5-Dimethyl-1,4-diferrocenylhex-2-yn-1-ylidene)(2,4,6-tri-tert-butylphenyl) phosphine (3) was obtained in the reaction of 2,4,6-tri-tert-butylphenyl phosphine (1) with 1,4-diferrocenyl butadiyne (2) in minor yields. Compound 3 was structurally characterized by single crystal X-ray diffraction. The molecular structure of 3 consists of a linear butyne C-4 backbone, which is in conjugation with a phosphene moiety resulting in the phosphapent-2-yn-4-ene motif with one ferrocenyl substituent bonded to a C-sp3 and the other one to the C-sp2 carbon atom. Both sandwich moieties are located at the same site of the C-4 axis opposing the tert-butyl groups. This results in an alternated stacking within the crystal packing along [0 1 0] with weak T-shaped pi interactions within the ferrocenyl containing layer. Electrochemical measurements revealed two reversible redox events for the two ferrocenyl groups at -20 mV and at 135 mV. (C) 2017 Elsevier B.V. All rights reserved.

Original languageEnglish
Pages (from-to)741-745
Number of pages5
JournalInorganica Chimica Acta
Volume471
DOIs
Publication statusPublished - 24 Feb 2018
Externally publishedYes

Cite this

Miesel, Dominique ; Korb, Marcus ; Hildebrandt, Alexander ; Lang, Heinrich. / Synthesis and crystal structure of an acetylenic ferrocenyl substituted phosphaalkene. In: Inorganica Chimica Acta. 2018 ; Vol. 471. pp. 741-745.
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abstract = "(E)-(5,5-Dimethyl-1,4-diferrocenylhex-2-yn-1-ylidene)(2,4,6-tri-tert-butylphenyl) phosphine (3) was obtained in the reaction of 2,4,6-tri-tert-butylphenyl phosphine (1) with 1,4-diferrocenyl butadiyne (2) in minor yields. Compound 3 was structurally characterized by single crystal X-ray diffraction. The molecular structure of 3 consists of a linear butyne C-4 backbone, which is in conjugation with a phosphene moiety resulting in the phosphapent-2-yn-4-ene motif with one ferrocenyl substituent bonded to a C-sp3 and the other one to the C-sp2 carbon atom. Both sandwich moieties are located at the same site of the C-4 axis opposing the tert-butyl groups. This results in an alternated stacking within the crystal packing along [0 1 0] with weak T-shaped pi interactions within the ferrocenyl containing layer. Electrochemical measurements revealed two reversible redox events for the two ferrocenyl groups at -20 mV and at 135 mV. (C) 2017 Elsevier B.V. All rights reserved.",
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author = "Dominique Miesel and Marcus Korb and Alexander Hildebrandt and Heinrich Lang",
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Synthesis and crystal structure of an acetylenic ferrocenyl substituted phosphaalkene. / Miesel, Dominique; Korb, Marcus; Hildebrandt, Alexander; Lang, Heinrich.

In: Inorganica Chimica Acta, Vol. 471, 24.02.2018, p. 741-745.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis and crystal structure of an acetylenic ferrocenyl substituted phosphaalkene

AU - Miesel, Dominique

AU - Korb, Marcus

AU - Hildebrandt, Alexander

AU - Lang, Heinrich

PY - 2018/2/24

Y1 - 2018/2/24

N2 - (E)-(5,5-Dimethyl-1,4-diferrocenylhex-2-yn-1-ylidene)(2,4,6-tri-tert-butylphenyl) phosphine (3) was obtained in the reaction of 2,4,6-tri-tert-butylphenyl phosphine (1) with 1,4-diferrocenyl butadiyne (2) in minor yields. Compound 3 was structurally characterized by single crystal X-ray diffraction. The molecular structure of 3 consists of a linear butyne C-4 backbone, which is in conjugation with a phosphene moiety resulting in the phosphapent-2-yn-4-ene motif with one ferrocenyl substituent bonded to a C-sp3 and the other one to the C-sp2 carbon atom. Both sandwich moieties are located at the same site of the C-4 axis opposing the tert-butyl groups. This results in an alternated stacking within the crystal packing along [0 1 0] with weak T-shaped pi interactions within the ferrocenyl containing layer. Electrochemical measurements revealed two reversible redox events for the two ferrocenyl groups at -20 mV and at 135 mV. (C) 2017 Elsevier B.V. All rights reserved.

AB - (E)-(5,5-Dimethyl-1,4-diferrocenylhex-2-yn-1-ylidene)(2,4,6-tri-tert-butylphenyl) phosphine (3) was obtained in the reaction of 2,4,6-tri-tert-butylphenyl phosphine (1) with 1,4-diferrocenyl butadiyne (2) in minor yields. Compound 3 was structurally characterized by single crystal X-ray diffraction. The molecular structure of 3 consists of a linear butyne C-4 backbone, which is in conjugation with a phosphene moiety resulting in the phosphapent-2-yn-4-ene motif with one ferrocenyl substituent bonded to a C-sp3 and the other one to the C-sp2 carbon atom. Both sandwich moieties are located at the same site of the C-4 axis opposing the tert-butyl groups. This results in an alternated stacking within the crystal packing along [0 1 0] with weak T-shaped pi interactions within the ferrocenyl containing layer. Electrochemical measurements revealed two reversible redox events for the two ferrocenyl groups at -20 mV and at 135 mV. (C) 2017 Elsevier B.V. All rights reserved.

KW - Phosphaalkene

KW - Solid-state structure

KW - Electrochemistry

KW - Ferrocene

KW - PHOSPHORUS-COMPOUNDS

KW - ALKYLIDENE PHOSPHINES

KW - DOUBLE-BOND

KW - ELECTROCHEMISTRY

KW - DERIVATIVES

KW - HETEROCYCLES

KW - AROMATICITY

KW - THIOPHENES

KW - COMPLEXES

KW - MOLECULES

U2 - 10.1016/j.ica.2017.12.014

DO - 10.1016/j.ica.2017.12.014

M3 - Article

VL - 471

SP - 741

EP - 745

JO - Inorganica Chemica Acta

JF - Inorganica Chemica Acta

SN - 0020-1693

ER -