The synthesis and electrochemical behavior of 1,4-di-(2,5-dimethylazaferrocenyl)-1,3-butadiyne

Kowalski, Konrad; Domagała, Sławomir

doi:10.1016/j.jorganchem.2007.03.015

Cited by 11 publications

(2 citation statements)

References 25 publications

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“…42,43 However, the result was unsatisfying, probably due to the low stability of 9 and/or 3b in the solution state under an oxidative environment. 2 Thus, Pd/Cucatalyzed homocoupling reaction conditions 44,45 were used for the synthesis of 3b and provide the product in 84% yield. This protocol abandons the use of virulent potassium cyanide that was needed for the release of the analogous bis(terpyridine) ligands after the Cu-promoted coupling reaction.…”

Section: Synthesismentioning

confidence: 99%

Ruthenium(ii) bis(terpyridine) electron transfer complexes with alkynyl–ferrocenyl bridges: synthesis, structures, and electrochemical and spectroscopic studies

Guo

Yan

et al. 2012

Dalton Trans.

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Two novel alkynyl-bridged symmetric bis-tridentate ligands 1,2-bis(1'-[4'-(2,2':6',2''-terpyridinyl)]ferrocenyl)ethyne (3a; tpy-Fc-C[triple bond]C-Fc-tpy; Fc = ferrocenyl; tpy = terpyridyl) and 1,4-bis(1'-[4'-(2,2':6',2''-terpyridinyl)]ferrocenyl)-1,3-butadiyne (3b; tpy-Fc-C[triple bond]C-C[triple bond]C-Fc-tpy) and their Ru(2+) complexes 6a and 6b have been synthesized and characterized by cyclic voltammetry, UV-vis and luminescence spectroscopy, and in the case of 3b by single-crystal X-ray diffraction. Cyclic voltammograms of both compounds, 3a and 3b, display two severely overlapping ferrocene-based oxidative peaks with only one reductive peak. The redox behavior of 6a and 6b is dominated by the Ru(2+)/Ru(3+) redox couple (E(1/2) from 1.33 to 1.34 V), the Fe(2+)/Fe(3+) redox couples (E(1/2) from 0.46 to 0.80 V), and the tpy/tpy(-)/tpy(2-) redox couples (E(1/2) from -1.19 to -1.48 V). The UV-vis spectra of 6a and 6b show absorption bands assigned to the (1)[(d(π)(Fe))(6)] → (1)[(d(π)(Fe))(5)(π*(tpy)(Ru))(1)] MMLCT transition at ~555 nm. Complexes and are luminescent in H(2)O-CH(3)CN (4 : 1, v/v) solution at room temperature, and 6b exhibits the strongest luminescence intensity (λ(max)(em): 710 nm, Φ(em): 2.28 × 10(-4), τ: 358 ns) relative to analogous ferrocene-based bis(terpyridine) Ru(II) complexes reported so far.

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Section: Synthesismentioning

confidence: 99%

Ruthenium(ii) bis(terpyridine) electron transfer complexes with alkynyl–ferrocenyl bridges: synthesis, structures, and electrochemical and spectroscopic studies

Guo

Yan

et al. 2012

Dalton Trans.

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“…Changing the R group in {[(salchda)RuC(OR)(CHCPh 2 )] 2 ·H} + from Et ( 1a ) to n -Pr ( 1b ) has no effect on the E 1/2 value of the couple. As the two ruthenium centers are not oxidized at the same potential, the existence of electronic communication between the two monomeric units is demonstrated …”

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confidence: 99%

Proton-Bridged Dinuclear (salen)Ru Carbene Complexes: Synthesis, Structure, and Reactivity of {[(salchda)Ru═C(OR)(CH═CPh₂)]₂·H}⁺

et al. 2008

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Mori–Hiyama versus Hay Coupling for Higher Polyynes

Gulia¹,

Osowska²,

Pigulski³

et al. 2012

Eur J Org Chem

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Dimerizations of C4 precursors RC≡CC≡CTMS [R = C6H5 (1), p‐CH3C6H5, (2), 4‐n‐C5H11C6H4 (3), C6H9 (4), p‐CH3OC6H4 (5), p‐C6H5COC6H4 (6), p‐NO2C6H4 (7), and p‐NCC6H4 (8)] by Hay coupling with in situ deprotection gave stable octatetraynes R(C≡C)4R (1–8‐C8‐1–8) in 42–80 % yields as light yellow to brown powders. The same tetraynes were next synthesized from the same C4 precursors by an alternative Mori–Hiyama method that typically utilizes trimethylsilyl‐substituted alkynes without prior deprotection. The latter protocol proved useful and gave the expected products but with lower yields of 8–74 %. The resulting tetraynes were characterized by spectroscopic methods and in some cases by X‐ray crystallography. In the cases of 1‐C8‐1 and 3‐C12‐3, close analysis of the crystal data showed high degrees of carbon chain linearity, with % contraction indexes of 0.13 % and 0.19 %, respectively. The chains were more strained in the cases of 6‐C8‐6 (0.34 %) and 3‐C8‐3 (0.68 %). Deeper analysis of packing motifs revealed 3‐C12‐3 to be a very promising candidate for topochemical 1,4‐polymerization.

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The synthesis and electrochemical behavior of 1,4-di-(2,5-dimethylazaferrocenyl)-1,3-butadiyne

Cited by 11 publications

References 25 publications

Ruthenium(ii) bis(terpyridine) electron transfer complexes with alkynyl–ferrocenyl bridges: synthesis, structures, and electrochemical and spectroscopic studies

Ruthenium(ii) bis(terpyridine) electron transfer complexes with alkynyl–ferrocenyl bridges: synthesis, structures, and electrochemical and spectroscopic studies

Proton-Bridged Dinuclear (salen)Ru Carbene Complexes: Synthesis, Structure, and Reactivity of {[(salchda)Ru═C(OR)(CH═CPh₂)]₂·H}⁺

Mori–Hiyama versus Hay Coupling for Higher Polyynes

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The synthesis and electrochemical behavior of 1,4-di-(2,5-dimethylazaferrocenyl)-1,3-butadiyne

Cited by 11 publications

References 25 publications

Ruthenium(ii) bis(terpyridine) electron transfer complexes with alkynyl–ferrocenyl bridges: synthesis, structures, and electrochemical and spectroscopic studies

Ruthenium(ii) bis(terpyridine) electron transfer complexes with alkynyl–ferrocenyl bridges: synthesis, structures, and electrochemical and spectroscopic studies

Proton-Bridged Dinuclear (salen)Ru Carbene Complexes: Synthesis, Structure, and Reactivity of {[(salchda)Ru═C(OR)(CH═CPh2)]2·H}+

Mori–Hiyama versus Hay Coupling for Higher Polyynes

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Proton-Bridged Dinuclear (salen)Ru Carbene Complexes: Synthesis, Structure, and Reactivity of {[(salchda)Ru═C(OR)(CH═CPh₂)]₂·H}⁺