Rigid <i>C</i><sub>3</sub>‐Symmetric Scaffolds Based on Adamantane

Pannier, Nadine; Maison, Wolfgang

doi:10.1002/ejoc.200701003

Cited by 37 publications

(35 citation statements)

References 56 publications

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“…A common synthetic precursor for the synthesis of suitable tripodal catecholates is the AB 3 -scaffold 1 [40–42] (Scheme 1) which is readily available in a few steps from adamantane as a cheap starting material [43]. Amine 1 was coupled to a commercially available PEG-carboxylate (5 kDa) with EDC/DMAP.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of tripodal catecholates and their immobilization on zinc oxide nanoparticles

Klitsche¹,

Ramcke²,

Migenda³

et al. 2015

Beilstein J. Org. Chem.

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SummaryA common approach to generate tailored materials and nanoparticles (NPs) is the formation of molecular monolayers by chemisorption of bifunctional anchor molecules. This approach depends critically on the choice of a suitable anchor group. Recently, bifunctional catecholates, inspired by mussel-adhesive proteins (MAPs) and bacterial siderophores, have received considerable interest as anchor groups for biomedically relevant metal surfaces and nanoparticles. We report here the synthesis of new tripodal catecholates as multivalent anchor molecules for immobilization on metal surfaces and nanoparticles. The tripodal catecholates have been conjugated to various effector molecules such as PEG, a sulfobetaine and an adamantyl group. The potential of these conjugates has been demonstrated with the immobilization of tripodal catecholates on ZnO NPs. The results confirmed a high loading of tripodal PEG-catecholates on the particles and the formation of stable PEG layers in aqueous solution.

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Section: Resultsmentioning

confidence: 99%

Synthesis of tripodal catecholates and their immobilization on zinc oxide nanoparticles

Klitsche¹,

Ramcke²,

Migenda³

et al. 2015

Beilstein J. Org. Chem.

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“…Additional benefits arise from the rigidity of the diamondoid cages allowing construction of various three-dimensional structures with well-defined and predictable topologies [5][6][7][8][9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Transition metal complexes with cage-opened diamondoid tetracyclo[7.3.1.1^4,12.0^2,7]tetradeca-6.11-diene

Valentin

Henß

Tkachenko

et al. 2015

Journal of Coordination Chemistry

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“…Since the key idea is to increase the dimensionality of planar molecules through structure engineering, one of the possible ways to achieve this is simply to incorporate three dimensional (3-D) alicyclic ring substituents into the molecular scaffold. [44][45][46][47][48][49] The effects of three dimensional alicyclic rigid systems on the solid state emission of luminescent polymers 50 as pendant units have been investigated. However, to the best of our knowledge, no efforts have been directed yet to investigate the effect of rigid 3-D arms on the ACQ problem/solid state emission of planar molecular systems.…”

Section: Introductionmentioning

confidence: 99%

Packing directed beneficial role of 3-D rigid alicyclic arms on the templated molecular aggregation problem

et al. 2015

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Subtle changes in molecular structure have been used to alter the molecular packing and optical properties of organic luminophores. Thus it is important to study simple and advantageous structural modification to overcome limitations of aggregation quenching of fluorescence. Planar conjugated organic compounds are unlikely to be used in OLED devices as they suffer with luminescence weakening due to p-p cofacial stacking and excimer formation in the solid state. To avoid such critical issues, doped device architecture for OLED devices has widely been adopted which actually complicates the device fabrication process. Thus an approach for delimiting these drawbacks using simple methodologies is highly desirable for cost effective OLED device fabrication. In this context, two 3-dimensional rigid arms have been introduced into a planar benzo[h]chromen-2-one core, which suffers from aggregation caused quenching, as peripheral substituents to tune the molecular packing and subsequently their optical properties. The resultant compounds 1 and 2 have been tested for non-doped and doped OLED device application. Compound 1 was found to be highly thermally stable with a decomposition temperature of 344 C. Single crystal XRD studies helped to elucidate that voluminous ring substituents are capable of eradicating co-facial p-p stacking by increasing the intermolecular distance and hence the luminescence in the solid state could be regenerated. This tuning of intermolecular distance between molecules helped to mitigate the close packed arrangement at a molecular level and also provided the bulk with the enhanced emission property. Electroluminescence from a pristine layer of compound 1 was possible. Thus an approach enabling planar luminophores to be used in OLED applications utilizing thin films of structurally engineered luminophores has been presented.

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Rigid C₃‐Symmetric Scaffolds Based on Adamantane

Cited by 37 publications

References 56 publications

Synthesis of tripodal catecholates and their immobilization on zinc oxide nanoparticles

Synthesis of tripodal catecholates and their immobilization on zinc oxide nanoparticles

Transition metal complexes with cage-opened diamondoid tetracyclo[7.3.1.1^4,12.0^2,7]tetradeca-6.11-diene

Packing directed beneficial role of 3-D rigid alicyclic arms on the templated molecular aggregation problem

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Rigid C3‐Symmetric Scaffolds Based on Adamantane

Cited by 37 publications

References 56 publications

Synthesis of tripodal catecholates and their immobilization on zinc oxide nanoparticles

Synthesis of tripodal catecholates and their immobilization on zinc oxide nanoparticles

Transition metal complexes with cage-opened diamondoid tetracyclo[7.3.1.14,12.02,7]tetradeca-6.11-diene

Packing directed beneficial role of 3-D rigid alicyclic arms on the templated molecular aggregation problem

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Rigid C₃‐Symmetric Scaffolds Based on Adamantane

Transition metal complexes with cage-opened diamondoid tetracyclo[7.3.1.1^4,12.0^2,7]tetradeca-6.11-diene