Synthesis of 1,4‐bis(4‐pyridyl)butadiyne

Ciana, Leopoldo Delia; Haim, Albert

doi:10.1002/jhet.5570210268

Cited by 117 publications

(44 citation statements)

References 9 publications

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“…Cl 2 ], [22] 4-ethynylpyridine, [23] Ln(diketonate) 3 ·2 H 2 O [24] (diketonate = tta, hfac) and 3-ethynyl-1,10-phenanthroline [25] were prepared according to literature methods. All other reagents were obtained from commercial sources (Avocado, Aldrich) and used as received.…”

Section: Methodsmentioning

confidence: 99%

Luminescent Pt^II(bipyridyl)(diacetylide) Chromophores with Pendant Binding Sites as Energy Donors for Sensitised Near‐Infrared Emission from Lanthanides: Structures and Photophysics of Pt^II/Ln^III Assemblies

Ronson¹,

Lazarides²,

Adams³

et al. 2006

Chemistry A European J

136

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The complexes [Pt(bipy){CC-(4-pyridyl)}(2)] (1) and [Pt(tBu(2)bipy){CC-(4-pyridyl)}(2)] (2) and [Pt(tBu(2)-bipy)(CC-phen)(2)] (3) all contain a Pt(bipy)(diacetylide) core with pendant 4-pyridyl (1 and 2) or phenanthroline (3) units which can be coordinated to {Ln(diketonate)(3)} fragments (Ln = a lanthanide) to make covalently-linked Pt(II)/Ln(III) polynuclear assemblies in which the Pt(II) chromophore, absorbing in the visible region, can be used to sensitise near-infrared luminescence from the Ln(III) centres. For 1 and 2 one-dimensional coordination polymers [1Ln(tta)(3)](infinity) and [2Ln(hfac)(3)](infinity) are formed, whereas 3 forms trinuclear adducts [3{Ln(hfac)(3)}(2)] (tta=anion of thenoyl-trifluoroacetone; hfac=anion of hexafluoroacetylacetone). Complexes 1-3 show typical Pt(II)-based (3)MLCT luminescence in solution at approximately 510 nm, but in the coordination polymers [1Ln(tta)(3)](infinity) and [2Ln(hfac)(3)](infinity) the presence of stacked pairs of Pt(II) units with short PtPt distances means that the chromophores have (3)MMLCT character and emit at lower energy ( approximately 630 nm). Photophysical studies in solution and in the solid state show that the (3)MMLCT luminescence in [1Ln(tta)(3)](infinity) and [2Ln(hfac)(3)](infinity) in the solid state, and the (3)MLCT emission of [3{Ln(hfac)(3)}(2)] in solution and the solid state, is quenched by Pt-->Ln energy transfer when the lanthanide has low-energy f-f excited states which can act as energy acceptors (Ln=Yb, Nd, Er, Pr). This results in sensitised near-infrared luminescence from the Ln(III) units. The extent of quenching of the Pt(II)-based emission, and the Pt-->Ln energy-transfer rates, can vary over a wide range according to how effective each Ln(III) ion is at acting as an energy acceptor, with Yb(III) usually providing the least quenching (slowest Pt-->Ln energy transfer) and either Nd(III) or Er(III) providing the most (fastest Pt-->Ln energy transfer) according to which one has the best overlap of its f-f absorption manifold with the Pt(II)-based luminescence.

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Section: Methodsmentioning

confidence: 99%

Luminescent Pt^II(bipyridyl)(diacetylide) Chromophores with Pendant Binding Sites as Energy Donors for Sensitised Near‐Infrared Emission from Lanthanides: Structures and Photophysics of Pt^II/Ln^III Assemblies

Ronson¹,

Lazarides²,

Adams³

et al. 2006

Chemistry A European J

136

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“…2-Methyl-4-(4-pyridyl)-3-butyn-2-ol was prepared according to the standard method (Ciana & Haim, 1984 (7) 0.0555 (2) 0.060 (2) C(3') 0.5641 (7) 0.5087 (7) 0.1198 (2) 0.054 (2) C(4') 0.6909 (7) 0.5314 (7) 0.1534 (2) 0.054 (2) C(5') 0.8473 (7) 0.4944 (6) 0.1371 (2) 0.044 (2) C(6') 0.9812 (7) 0.5102 (7) 0.1728 (2) 0.052 (2) C(7') 1.0831 (8) 0.5189 (6) 0.2062 (2) 0.049 (2) C(8 t)…”

Section: Methodsmentioning

confidence: 99%

2-Methyl-4-(4-pyridyl)-3-butyn-2-ol: a two-dimensional hydrogen-bond network

Pollagi¹,

Geib²,

Hopkins³

1994

Acta Crystallogr C

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“…Tetrahydrofuran was dried over CaH 2 and was freshly distilled prior to use. Compounds 1, 4-bis(4'-pyridylethynyl)benzene (bpeb), 1,4-bis (4'-pyridylethynyl)naphthalene (bpen) and 1,4-bis (4'-pyr idylethynyl)anthracene (bpea) were synthesized by published methods [16][17][18] . The details of the synthesis of 1 have already been published 19,20 .…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Photophysical Properties of Rhenium(I)-Alkynyl Molecular Rectangles

Ramdass

Sathish²,

Manimaran³

et al. 2016

Orient. J. Chem

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A series of highly conjugated, rigid Re(I)-based molecular rectangles {[fac-Re(CO) 3 Br] 2 (µ-bpy) (µ-L)} 2 (1, L = 1,4-bis(42 -pyridylethynyl)benzene, bpeb; 2, L = 1,4-bis(42 -pyridylethynyl)naphthalene, bpen; 3, L = 1,4-bis(42 -pyridylethynyl)anthracene, bpea; and bpy = 4,42 -bipyridine) containing two different types of pyridyl ligands were synthesized, characterized and their photophysical properties studied. Successful emission color tuning was achieved by incorporating rigid alkynyl ligands into the Re(I) rectangles. Complexes 1-3 exhibited an intense absorption bands with a high e value at > 340 nm in THF solution, which is attributed to mixed two metal-to-ligand charge transfer dp(Re) → p*(bpy) and dp(Re) → p*(alkynyl)) along with ligand-to-ligand charge transfer ( 1 LLCT)/ and intraligand charge transfer ( 1 ILCT) transitions. Compound 1 featured a broad and structureless emission band at 619 nm, which was attributed to the emission of 3 MLCT dp(Re) → p*(bpy) and/or [dp(Re) → p*(alkynyl)] characteristics with an additional luminescence at 431 nm. Whereas complexes 2 and 3 displayed an intraligand (IL) emission at 445 and 489(sh), 521 nm. These compounds represent a new class of visible light-harvesting materials that exhibit greatly enhanced emission decay lifetimes as a result of intervening ligand triplet states ( 3 LLCT/ 3 ILCT) present on the alkynyl appended naphthalene and anthracene chromophores, as evidenced by transient absorption spectra.

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Synthesis of 1,4‐bis(4‐pyridyl)butadiyne

Cited by 117 publications

References 9 publications

Luminescent Pt^II(bipyridyl)(diacetylide) Chromophores with Pendant Binding Sites as Energy Donors for Sensitised Near‐Infrared Emission from Lanthanides: Structures and Photophysics of Pt^II/Ln^III Assemblies

Luminescent Pt^II(bipyridyl)(diacetylide) Chromophores with Pendant Binding Sites as Energy Donors for Sensitised Near‐Infrared Emission from Lanthanides: Structures and Photophysics of Pt^II/Ln^III Assemblies

2-Methyl-4-(4-pyridyl)-3-butyn-2-ol: a two-dimensional hydrogen-bond network

Synthesis and Photophysical Properties of Rhenium(I)-Alkynyl Molecular Rectangles

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Synthesis of 1,4‐bis(4‐pyridyl)butadiyne

Cited by 117 publications

References 9 publications

Luminescent PtII(bipyridyl)(diacetylide) Chromophores with Pendant Binding Sites as Energy Donors for Sensitised Near‐Infrared Emission from Lanthanides: Structures and Photophysics of PtII/LnIII Assemblies

Luminescent PtII(bipyridyl)(diacetylide) Chromophores with Pendant Binding Sites as Energy Donors for Sensitised Near‐Infrared Emission from Lanthanides: Structures and Photophysics of PtII/LnIII Assemblies

2-Methyl-4-(4-pyridyl)-3-butyn-2-ol: a two-dimensional hydrogen-bond network

Synthesis and Photophysical Properties of Rhenium(I)-Alkynyl Molecular Rectangles

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Luminescent Pt^II(bipyridyl)(diacetylide) Chromophores with Pendant Binding Sites as Energy Donors for Sensitised Near‐Infrared Emission from Lanthanides: Structures and Photophysics of Pt^II/Ln^III Assemblies

Luminescent Pt^II(bipyridyl)(diacetylide) Chromophores with Pendant Binding Sites as Energy Donors for Sensitised Near‐Infrared Emission from Lanthanides: Structures and Photophysics of Pt^II/Ln^III Assemblies