Self-assembly of supramolecular oligo-phenylene-ethynylene wires consisting of double Hamilton receptor modified OPE rods and a tetraphenylporphyrin cyanurate

Wessendorf, Florian; Hirsch, Andreas

doi:10.1016/j.tet.2008.08.054

Cited by 23 publications

(19 citation statements)

References 56 publications

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“…The preparation of fullerenophosphates 3 – 11 was recently reported 14. 1,3,5‐Tris‐(2′‐methylmalonyl)ethoxymethylbenzene ( 18 )24 and Zn‐porphyrin 28 25 were prepared according to a literature procedure.…”

Section: Methodsmentioning

confidence: 99%

Facile Access to Functional Building Blocks of C₆₀ Involving C₃‐Symmetrical Addition Patterns

Gmehling

Hirsch

2013

Eur J Org Chem

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A new class of C3‐symmetrical fullerene building blocks with a well‐defined spatial arrangement of addends has been developed. They comprise compounds with a e,e,e‐trisaddition pattern and a mixed octahedral hexakisaddition pattern. Fullerenophosphates with a e,e,e‐addition pattern were used for the spatial preorganization of the addends. After deprotection seven different trisbromides (12–16, 15a, 16a) with varying chain lengths and orientation of the functional groups were obtained. Acetylenes could be coupled to these compounds by click chemistry through an intermediate trisazide. For the synthesis of mixed hexakisadducts 19–21 a template system based on a central benzyl moiety was attached to the free hemisphere of the trisadduct fullerenophosphates. It was shown that the phosphate and the benzyl template can be removed independently. Fully deprotected building block 24 bearing both terminal bromide and hydroxy moieties was prepared. In addition, rather complex hybrid architecture 29 bearing three porphyrin units in the polar addend zone was successfully synthesized.

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Section: Methodsmentioning

confidence: 99%

Facile Access to Functional Building Blocks of C₆₀ Involving C₃‐Symmetrical Addition Patterns

Gmehling

Hirsch

2013

Eur J Org Chem

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“…Deprotected ethinyl (metallo)porphyrins 6 a and 6 b were obtained in good yields. Next, an iodine‐substituted Hamilton receptor ( 7 ) and an iodine‐substituted cyanurate ( 8 ) were prepared according to literature procedures [20a, 28] . These building blocks were then coupled to the asymmetric ethinyl (metallo)porphyrins in a Sonogashira cross‐coupling reaction.…”

Section: Resultsmentioning

confidence: 99%

Non‐Covalent Postfunctionalization of Dye Layers on TiO₂ — A Tool for Enhancing Injection in Dye‐Sensitized Solar Cells

Luchs

Zieleniewska

Kunzmann

et al. 2021

Chemistry A European J

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We report on newly tailored dye layers, which were employed, on one hand, for covalent deposition and, on the other hand, for non‐covalently post‐functionalizing TiO2 nanoparticle films. Our functionalization concept enabled intermixing a stable covalent attachment of a first layer with a highly versatile and reversible hydrogen bonding through the Hamilton receptor–cyanuric acid binding motif as a second layer. Following this concept, we integrated step‐by‐step a first porphyrin layer and a second porphyrin/BODIPY layer. The individual building blocks and their corresponding combinations were probed with regard to their photophysical properties, and the most promising combinations were implemented in dye‐sensitized solar cells (DSSCs). Relative to the first porphyrin layer adding the second porphyrin/BODIPY layers increased the overall DSSC efficiency by up to 43 %.

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“…Compounds 1, 2, 3, 11, and 17 were synthesized according to literature procedures. [19][20][21]23,25] The preparation of chiral depsipeptide dendrons 21-23 and the fullerene derivative 20 was described previously. [10a,16] Solvents were dried by using standard techniques, anhydrous DMF was obtained from Acros.…”

Section: Methodsmentioning

confidence: 99%

“…Scheme 1 sketches the synthetic route to the iodine-substituted Hamilton receptor derivative 3, [19] which was used as a starting material for the targeted porphyrin guest molecules. In particular, heating of 5-iodobenzene-1,3-dioic acid (1) [20] with thionyl chloride (SOCl 2 ) at reflux, followed by coupling of the dichloride with N-(6-aminopyridin-2-yl)-3,3-dimethylbutanamide (2) [21] in tetrahydrofuran (THF) in situ afforded the iodine-substituted Hamilton receptor 3 in 73 % isolated yield.…”

Section: Synthesis Of the Hamilton Receptor Substituted Porphyrin Dermentioning

confidence: 99%

Self‐Assembling Depsipeptide Dendrimers and Dendritic Fullerenes with New cis‐ and trans‐Symmetric Hamilton Receptor Functionalized Zn–Porphyrins: Synthesis, Photophysical Properties and Cooperativity Phenomena

et al. 2010

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Two novel supramolecular building blocks, namely cis-and trans-symmetric zinc-porphyrins bearing Hamilton receptors as their focal points (10 and 15), were self-assembled with (i) first-, second-and third-generation depsipeptide cyanurates (21-23); (ii) second-generation dendrofullerene (24), and (iii) cyanuric acid substituted fullerene (20), and probed in a series of photophysical investigations. Importantly, an overall 1:2 stoichiometry was confirmed with binding con-

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Self-assembly of supramolecular oligo-phenylene-ethynylene wires consisting of double Hamilton receptor modified OPE rods and a tetraphenylporphyrin cyanurate

Cited by 23 publications

References 56 publications

Facile Access to Functional Building Blocks of C₆₀ Involving C₃‐Symmetrical Addition Patterns

Facile Access to Functional Building Blocks of C₆₀ Involving C₃‐Symmetrical Addition Patterns

Non‐Covalent Postfunctionalization of Dye Layers on TiO₂ — A Tool for Enhancing Injection in Dye‐Sensitized Solar Cells

Self‐Assembling Depsipeptide Dendrimers and Dendritic Fullerenes with New cis‐ and trans‐Symmetric Hamilton Receptor Functionalized Zn–Porphyrins: Synthesis, Photophysical Properties and Cooperativity Phenomena

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Self-assembly of supramolecular oligo-phenylene-ethynylene wires consisting of double Hamilton receptor modified OPE rods and a tetraphenylporphyrin cyanurate

Cited by 23 publications

References 56 publications

Facile Access to Functional Building Blocks of C60 Involving C3‐Symmetrical Addition Patterns

Facile Access to Functional Building Blocks of C60 Involving C3‐Symmetrical Addition Patterns

Non‐Covalent Postfunctionalization of Dye Layers on TiO2 — A Tool for Enhancing Injection in Dye‐Sensitized Solar Cells

Self‐Assembling Depsipeptide Dendrimers and Dendritic Fullerenes with New cis‐ and trans‐Symmetric Hamilton Receptor Functionalized Zn–Porphyrins: Synthesis, Photophysical Properties and Cooperativity Phenomena

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Facile Access to Functional Building Blocks of C₆₀ Involving C₃‐Symmetrical Addition Patterns

Facile Access to Functional Building Blocks of C₆₀ Involving C₃‐Symmetrical Addition Patterns

Non‐Covalent Postfunctionalization of Dye Layers on TiO₂ — A Tool for Enhancing Injection in Dye‐Sensitized Solar Cells