Synthesis, characterization and inclusion into liposomes of a new cationic pyrenyl amphiphile

Petaccia, Manuela; Giansanti, Luisa; Leonelli, Francesca; Bella, Angela La; Villalva, Denise Gradella; Mancini, Giovanna

doi:10.1016/j.chemphyslip.2016.08.001

Cited by 12 publications

(6 citation statements)

References 43 publications

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“…The supramolecular structures of thin films of the reference amphiphile 5_5 produced by means of the LB technique have been detailed recently . It was found that the combination between dipolarity and amphiphilicity in 5_5 yields two solid phases, as revealed by the minimum in the compressibility modulus C S –1 = − A dΠ/d A − at 30 Å 2 (see Figure A) . In the first phase ( A 0,I > 30 Å 2 ), 5_5 is anchored in the subphase via the carboxylic acid and the amino groups, as revealed by weakening the anchor strength of the latter upon increasing the subphase basicity (see isotherm shifts in Figure ).…”

Section: Resultsmentioning

confidence: 99%

Arylic versus Alkylic—Hydrophobic Linkers Determine the Supramolecular Structure and Optoelectronic Properties of Tripodal Amphiphilic Push–Pull Thiazoles

et al. 2019

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The supramolecular structures and their constituents essentially determine the optoelectronic properties of thin films. The introduction of amphiphilicity to the constituents and interface assembly is one established technique to control supramolecular structures and resulting material properties. To yield amphiphilicity, rather hydrophobic chromophores are linked to hydrophilic head groups via flexible alkyl chains. In the present work, we investigate whether replacement of the alkyl linkers by a phenylene linker, that is, replacing an electrically isolating moiety with a potentially semiconducting one, increases the conductivity through the resulting layers. After investigating the influence of the linker on molecular properties of the 2-(4-N,N-dimethylaminophenyl)-4-hydroxy-5-nitrophenyl-1,3 thiazoles exemplarily used in this work, we produce supramolecular structures by means of the Langmuir–Blodgett (LB) technique. Atomic force microscopy (AFM) and UV–vis absorption spectroscopy reveal that thin films made from the more rigid thiazole bearing the arylic linker feature a more homogeneous and stable supramolecular structure as compared to those made from the thiazole dye containing the flexible alkylic linker. Finally, conductive AFM (cAFM) results disclose that the LB films made from the thiazole bearing the π-conjugated arylic linker are less conductive than their counterparts based on the alkylic linkers. In the latter layers, the alkylic linkers provide sufficient motional degrees of freedom to allow for supramolecular rearrangement upon electrical operation during cAFM measurements, hence yielding supramolecular structures featuring increased conductivity with successive cAFM measurements. This work highlights the importance of supramolecular structures for optoelectronic properties by presenting a case where supramolecular effects excel the property changes introduced by molecular modifications.

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Section: Resultsmentioning

confidence: 99%

Arylic versus Alkylic—Hydrophobic Linkers Determine the Supramolecular Structure and Optoelectronic Properties of Tripodal Amphiphilic Push–Pull Thiazoles

et al. 2019

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“…Polycyclic aromatic hydrocarbons (PAHs), including derivatives of pyrene, have for some time been attracting attention due to their potential applications as optoelectronic materials (Anthony, 2008;Figueira-Duarte & Mü llen, 2011) or luminescent markers (Faggi et al, 2016;Aparin et al, 2017) as well as due to the relative ease of chemical modification. Their ability to form aggregates, ranging from -stacked dimers to more intricate arrangements (Hinoue et al, 2012) both in solution and in the solid state, is vital to many of these applications, together with their general sensitivity to environment (Petaccia et al, 2016;Niko et al, 2012), which manifests for instance in varying spectroscopic properties. There are known cases, where certain modes of aggregation in the solid state significantly enhanced luminescence of such compounds (Hinoue et al, 2012;Flamholc et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

Structure and piezochromism of pyrene-1-carbaldehyde at high pressure

Tchoń

Makal

2019

Acta Crystallogr Sect B

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The crystal structure of pyrene-1-carbaldehyde (PA), a model polyaromatic hydrocarbon, highly luminescent in the solid state and crystallizing in the triclinic system, has been re-determined at several pressures ranging from atmospheric up to 3 GPa using a diamond anvil cell. A 'multi-crystal' approach was used in crystal structure determination, significantly improving completeness of X-ray diffraction data attainable for such a low-symmetry system. The crystal structure consists of infinite -stacks of PA molecules with discernible dimers, which resemble aggregates formed by pyrene derivatives in solution as well as in the solid state. A series of measurements showed that the average inter-planar distance between individual molecules within -stacks decreases with pressure in the investigated range. This results in piezochromic properties of PA: a significant sample color change as well as a red-shift of fluorescence with pressure, as studied with UV-vis spectroscopy. Periodic DFT calculations allowed us to relate the variations in the crystal structure with pressure to the changes in the electronic structure of this material. research papers Acta Cryst. (2019). B75, 343-353 Tchoń and Makal Structure and piezochromism of pyrene-1-carbaldehyde 353

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“…In the frame of biological active compound synthesis [ 10 , 11 , 12 ], we focused on the preparation of 2-( N -acetyl)- l -phenylalanylamido-2-deoxy- d -glucose (NAPA) [ 13 ], an N -acetyl- l -phenylalanine bioactive derivative of glucosamine hydrochloride (Glu) that has shown interesting chondroprotective action in the field of joint degenerative diseases [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

N-Acetyl-l-phenylalanine Racemization during TBTU Amidation: An In-Depth Study for the Synthesis of Anti-Inflammatory 2-(N-Acetyl)-l-phenylalanylamido-2-deoxy-d-glucose (NAPA)

et al. 2023

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A thorough study on the amidation conditions of N-acetyl-l-phenylalanine using TBTU and various bases is reported for the synthesis of 2-(N-acetyl)-l-phenylalanylamido-2-deoxy-d-glucose (NAPA), a promising drug for the treatment of joints diseases. TBTU-mediated diastereoselective amidation reaction with 1,3,4,6-tetra-O-acetyl-β-d-glucosamine always gave racemization of N-acetyl-l-phenylalanine. The stereochemical retention under amidation conditions was studied in detail in the presence of difference bases and via other control experiments, evidencing the possibility to reduce racemization using pyridine as base.

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Synthesis, characterization and inclusion into liposomes of a new cationic pyrenyl amphiphile

Cited by 12 publications

References 43 publications

Arylic versus Alkylic—Hydrophobic Linkers Determine the Supramolecular Structure and Optoelectronic Properties of Tripodal Amphiphilic Push–Pull Thiazoles

Arylic versus Alkylic—Hydrophobic Linkers Determine the Supramolecular Structure and Optoelectronic Properties of Tripodal Amphiphilic Push–Pull Thiazoles

Structure and piezochromism of pyrene-1-carbaldehyde at high pressure

N-Acetyl-l-phenylalanine Racemization during TBTU Amidation: An In-Depth Study for the Synthesis of Anti-Inflammatory 2-(N-Acetyl)-l-phenylalanylamido-2-deoxy-d-glucose (NAPA)

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