Synthesis and Aggregation Properties of Polycationic Perylenetetracarboxylic Acid Diimides

Schönamsgruber, Jörg; Schade, Boris; Kirschbaum, Rolf W.; Li, Jing; Bauer, Walter; Böttcher, Christoph; Drewello, Thomas; Hirsch, Andreas

doi:10.1002/ejoc.201201062

Cited by 17 publications

(16 citation statements)

References 25 publications

(21 reference statements)

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“…[9] This dendron was also utilized in synthesis of dendritic perylenes that are suitable for the chemical functionalization of inorganic nanoparticles and dendronized polycationic perylenetetracarboxylic acid diimides. [10,11] Newkome-type dendronized norbornene macromonomers were synthesized and polymerized by ring-opening metathesis polymerization to obtain biocompatible polymers. [12] This dendron was also used in synthesis of protein cages to construct synthetic DNAbinding domains, [13] redox active hybrid dendrimers building blocks for nonviral vectors for gene therapies, [14] stabilization of gold particles, [15,16] and catalyst in transfer hydrogenation [17] as well as micelles [18] and ion selective gels after hydrolysis.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of linear dendritic homo and copolymers acrylated behera amine

Esen

2015

Designed Monomers and Polymers

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A co-polymerizable dendron of first generation synthesized from behera amine was homopolymerized and copolymerized with commercial monomers such as styrene, methyl methacrylate, and N-vinyl pyrrolidone. Characterization of the co-polymers was performed and it was found with the help of FT-IR and proton and carbon NMR that copolymerizable dendron, ACTES (ACrylated TriESter, first-generation dendron of acrylated behera amine) was incorporated in the co-polymer chains. Besides, the reactivity ratio pairs of the ACTES monomer with both styrene and n-vinyl pyrrolidone were determined. The reactivity ratio pair for ACTES and MMA could not be determined by neither gravimetrically nor with NMR. After experiments and calculations, the reactivity ratio pair for styrene and ACTES was found to be r st = 0.27 and r ac = 0.44 and for NVP and ACTES r nvp = 0.36 and r ac = 1.01. By utilization of the reactivity ratio of ACTES, "Q" and "e" values were determined in order to be able to draw some conclusions about the reactivity behavior during copolymerizations. "Q" = 1.152 and "e" = 0.66 were found with respect to styrene as reference. These values indicates the steric effect of ACTES was more dominant in copolymerizations.

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Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of linear dendritic homo and copolymers acrylated behera amine

Esen

2015

Designed Monomers and Polymers

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“…2014, 20, 16969 -16979 www.chemeurj.org Experimental Section 1,6,7,12-Tetra(4-tert-butylphenoxy)-perylene-3,4:9,10-tetracarboxylic acid dianhydride was synthesized according to the literature. [11,27] Chemicals were ordered from Aldrich or Acros Organics and were used as received. Quinoline was used freshly distilled and handled under argon atmosphere.…”

Section: Resultsmentioning

confidence: 99%

Fused Perylene–Phthalocyanine Macrocycles: A New Family of NIR‐Dyes with Pronounced Basicity

Schönamsgruber

Maid

Bauer

et al. 2014

Chemistry A European J

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The synthesis and characterization of a new type of chromophore, namely PePc consisting of a central phthalocyanine core and four fused perylene-bisimide (PBI) units is described for the first time. The entire architecture represents a highly extended conjugated heterocyclic π-system with C4h symmetry. In order to guarantee pronounced solubility in organic solvents the corresponding PBI units were bay-functionalized with tert-butylphenoxy substituents. Next to the metal-free macrocycle, PePcH2 , also metallated macrocycles PePcM (M=Zn, Ni, Pb, Ru, Fe) were synthesized. The extensive fusion of the corresponding aromatic building blocks to the very large extended π-system leads to a very narrow HOMO-LUMO gap and as a consequence to transparency in the visible but light absorption in the NIR region. Significantly, the azomethine N-atoms N1N4 of PePcM and PePcH2 are highly basic. The corresponding tetraprotonated systems can only be deprotonated with very strong non-nucleophilic bases such as phosphazene bases. In the protonated forms PePcMH4 (4+) and PePcMH6 (4+) the absorption maximum is shifted back to the visible region due to the loss of conjugation. The experimental findings were corroborated with quantum mechanical calculations.

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“…2‐(2‐(2‐Hydroxyethoxy)ethoxy)ethyl dodecanoate ( 4 ) and fluorescent perylene bisimide amphiphiles 10 were synthesized according to literature procedures …”

Section: Methodsmentioning

confidence: 99%

Manufacturing Nanoparticles with Orthogonally Adjustable Dispersibility in Hydrocarbons, Fluorocarbons, and Water

et al. 2018

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We describe a universal wet‐chemical shell‐by‐shell coating procedure resulting in colloidal titanium dioxide (TiO2) and iron oxide (Fe3O4) nanoparticles with dynamically and reversibly tunable surface energies. A strong covalent surface functionalization is accomplished by using long‐chained alkyl‐, triethylenglycol‐, and perfluoroalkylphosphonic acids, yielding highly stabilized core–shell nanoparticles with hydrophobic, hydrophilic, or superhydrophobic/fluorophilic surface characteristics. This covalent functionalization sequence is extended towards a second noncovalent attachment of tailor‐made nonionic amphiphilic molecules to the pristine coated core–shell nanoparticles via solvophobic (i.e. either hydrophobic, lipophobic, or fluorophobic) interactions. Thereby, orthogonal tuning of the surface energies of nanoparticles via noncovalent interactions is accomplished. As a result, this versatile bilayer coating process enables reversible control over the colloidal stability of the metal oxide nanoparticles in fluorocarbons, hydrocarbons, and water.

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Synthesis and Aggregation Properties of Polycationic Perylenetetracarboxylic Acid Diimides

Cited by 17 publications

References 25 publications

Synthesis and characterization of linear dendritic homo and copolymers acrylated behera amine

Synthesis and characterization of linear dendritic homo and copolymers acrylated behera amine

Fused Perylene–Phthalocyanine Macrocycles: A New Family of NIR‐Dyes with Pronounced Basicity

Manufacturing Nanoparticles with Orthogonally Adjustable Dispersibility in Hydrocarbons, Fluorocarbons, and Water

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