Oligo(U-terpyridines) and Their Ruthenium(II) Complexes:  Synthesis and Structural Properties

Winter, Andreas; Hummel, Johanna; Risch, Nikolaus

doi:10.1021/jo060387+

Cited by 29 publications

(26 citation statements)

References 69 publications

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“…Risch and co‐workers reported the synthesis of new star‐shaped tris‐(U‐terpyridine) 355 and the corresponding trinuclear ruthenium(II) complex ( 356 ), and studied the electronic and electrochemical behavior of complex 356 . Star‐shaped molecule 286 was derived from bromoacetophenone by following a two‐step literature sequence.…”

Section: Carbon−nitrogen Bond‐forming Reactionsmentioning

confidence: 99%

Synthetic Approaches to Star‐Shaped Molecules with 1,3,5‐Trisubstituted Aromatic Cores

Kotha

Meshram

Panguluri

et al. 2019

Chemistry An Asian Journal

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Herein, we summarize the synthetic approaches that have been developed for the synthesis of star‐shaped molecules. Typically, to design such highly functionalized molecules, simple building blocks are first assembled through trimerization reactions, starting from commercially available starting materials. Then, these building blocks are synthetically manipulated to generate extended star‐shaped molecules. We also discuss the syntheses of star‐shaped molecules that contain 2,4,6‐trisubstituted 1,3,5‐triazine or 1,3,5‐trisubstituted benzene rings as a central core and diverse substituted styrene, phenyl, and fluorene derivatives at their periphery, which endows these molecules with extended conjugation. A variety of metal‐catalyzed reactions, such as Suzuki, Buchwald–Hartwig, Sonogashira, Heck, and Negishi cross‐coupling reactions, as well as metathesis, have been employed to functionalize a range of star‐shaped molecules. The methods described herein will be helpful for designing a wide range of intricate compounds that are highly valuable in the fields of supramolecular chemistry and materials science. Owing to space limitations, we will not cover all of the publications on this topic. Instead, we will focus on examples that were reported by our research group and other relevant recent literature. Apart from the trimerization sequence, this Minireview has been structured based on the key reactions that were used to prepare the star‐shaped molecules and other higher analogues. Finally, some examples that do not fit into this classification are discussed.

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Section: Carbon−nitrogen Bond‐forming Reactionsmentioning

confidence: 99%

Synthetic Approaches to Star‐Shaped Molecules with 1,3,5‐Trisubstituted Aromatic Cores

Kotha

Meshram

Panguluri

et al. 2019

Chemistry An Asian Journal

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“…In fact the latter are versatile intermediates for the preparation of terpyridine derivatives in a twofold domino‐sequence . This allowed the preparation of bis‐terpyridine 19 , according to the mechanism depicted in Scheme .…”

Section: Synthesis Of Thiophene‐containing 22′:6′2″‐terpyridinesmentioning

confidence: 99%

2,2′:6′,2″‐Terpyridines Functionalized with Thienyl Substituents: Synthesis and Applications

Husson

Knorr

2012

Journal of Heterocyclic Chem

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This review deals with the synthesis and applications of 2,2 0 :6 0 ,2 00 -terpyridines which are functionalized with thiophene ring, directly linked to the terpyridine core or via a spacer. Two main methodologies were used, ring closure of diketo-derivatives and cross coupling reactions. The obtained compounds find applications in various fields especially in material sciences such as solar cells or macromolecular sciences. Scheme 4. Synthesis of thienyl-containing quaterpyridine. Scheme 5 456

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“…Due to the highly rigid structure and the absence of any solubilizing side chains, only very low solubility of the bis(terpyridine) 7 in common organic solvents was observed. 23 Nonetheless, this example shows that the click chemistry approach is also suited for the straightforward construction of p-conjugated rigid-linear terpyridyl derivatives with potential in the design of new functional materials by transition metal ion complexation.…”

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confidence: 99%

Azido- and Ethynyl-Substituted 2,2′:6′,2′′-Terpyridines as Suitable Substrates for Click Reactions

Winter¹,

Wild²,

Hoogenboom³

et al. 2009

Synthesis

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The click reaction of azido-and ethynyl-functionalized terpyridines has been exploited to obtain a series of 1H-1,2,3-triazole-substituted terpyridines. This protocol was extended towards the synthesis of terpyridine-based macroligands via end group modification of ethynyl-functionalized polymers. Finally, the combination of two orthogonal terpyridines within one click reaction highlights the potential of this approach with respect to the preparation of new building blocks for supramolecular assemblies and functional materials. Supramolecular chemistry has evolved into one of the most active research areas in modern chemistry with the design and preparation of new functional ligands and their incorporation into supramolecular assemblies by transition metal complexation, p-p stacking, or hydrogen bonding as cornerstones of this field. 1 In general, supramolecular interactions are weaker than covalent bonds, and therefore they can be easily affected by external parameters (e.g., pH, temperature, solvent, redox processes, and shear forces) allowing the design of responsive and 'smart' materials with potential self-healing properties. 2The remarkably high binding affinity towards most transition metal ions, together with their chelating properties, make terpyridines attractive building blocks for the construction of supramolecular assemblies. 3 Recently, oligopyridyl ligands and, in particular, their transition metal complexes have found applications as luminescent sensors in molecular biology and medical diagnostics, in photocatalysis, as active materials in self-assembled molecular devices, and as photoactive molecular wires and they have been used for storage applications in molecular electronics and photonics. 4,5 The basic principles and binding moieties known from supramolecular chemistry have successfully been introduced in the field of polymer chemistry, bringing together the characteristics from both fields: the intrinsic material properties arising from the polymer backbone, as well as the reversible self-assembly properties of the supramolecular moieties attached to the polymeric structure. 1b,c We have introduced a range of polymeric materials into such assemblies by this approach. 6 For this purpose, a variety of modified chelating ligands have been used successfully as initiators, monomers, or terminating agents. 1a Furthermore, the complexes have been utilized as supramolecular linkers between two polymeric chains to obtain well-defined homo and block copolymers, as well as chain-extended polymers. 1aThe Huisgen 1,3-dipolar cycloaddition, the so-called 'click' reaction, 7 has been used in the field of polymer chemistry for the covalent linkage of suitable functionalized polymers as well as for end group modification reactions. 8 Additionally, the click reaction has been introduced as a versatile tool for the attachment of organic substrates to surfaces and nanoparticles. 9 In continuation of previous work we have now combined the wide scope 10 of the click reaction with the chemistry of functionaliz...

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Oligo(U-terpyridines) and Their Ruthenium(II) Complexes: Synthesis and Structural Properties

Cited by 29 publications

References 69 publications

Synthetic Approaches to Star‐Shaped Molecules with 1,3,5‐Trisubstituted Aromatic Cores

Synthetic Approaches to Star‐Shaped Molecules with 1,3,5‐Trisubstituted Aromatic Cores

2,2′:6′,2″‐Terpyridines Functionalized with Thienyl Substituents: Synthesis and Applications

Azido- and Ethynyl-Substituted 2,2′:6′,2′′-Terpyridines as Suitable Substrates for Click Reactions

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