Dataset Information

Synthesis and Liquid Crystalline Properties of Unsymmetrically Substituted Naphthalenediimides with a Polar Headgroup: Effect of Amide Hydrogen Bonding and Alkyl Chain Length.

ABSTRACT: A series of new unsymmetrically substituted naphthalenediimide (NDI) moieties NDI-1 to NDI-6 were synthesized. The structures of these compounds were confirmed by means of FT-IR, ¹H?NMR, ¹³C?NMR, ESI-mass and HRMS spectroscopic measurements. UV/Vis and fluorescence spectroscopy were employed to investigate the photophysical properties of the prepared compounds in solution and in the solid state. Using the onset of UV/Vis absorption, the optical band gaps were calculated. Cyclic voltammetry measurements were performed to study the electrochemical behavior and to calculate the LUMO energy levels. The thermal properties of NDI derivatives were studied by differential scanning calorimetry. The mesomorphic birefringent behavior of the NDI derivatives was investigated with polarizing optical microscopy. Among all of the studied NDI derivatives, only NDI-1, NDI-2, and NDI-3 showed liquid crystalline texture, owing to the presence of an amide linkage for H-bonding along with aromatic moieties for ?-?-stacking.

SUBMITTER: Ghule NV

PROVIDER: S-EPMC5754548 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

Synthesis and Liquid Crystalline Properties of Unsymmetrically Substituted Naphthalenediimides with a Polar Headgroup: Effect of Amide Hydrogen Bonding and Alkyl Chain Length.

Ghule Namdev V NV Bhosale Rajesh S RS Bhosale Sidhanath V SV Srikanth Turlapati T Rao Nandiraju V S NVS Bhosale Sheshanath V SV

ChemistryOpen 20171115 1

A series of new unsymmetrically substituted naphthalenediimide (NDI) moieties NDI-1 to NDI-6 were synthesized. The structures of these compounds were confirmed by means of FT-IR, 1H NMR, 13C NMR, ESI-mass and HRMS spectroscopic measurements. UV/Vis and fluorescence spectroscopy were employed to investigate the photophysical properties of the prepared compounds in solution and in the solid state. Using the onset of UV/Vis absorption, the optical band gaps were ...[more]

PMID: 29318098

Similar Datasets

Project description:Ceramide is a major actor in the sphingolipid signaling pathway elicited by various kinds of cell stress. Under those conditions ceramide (Cer) is produced in the plasma membrane as a product of sphingomyelin (SM) hydrolysis, and this may lead to apoptosis. Thus, SM and Cer coexist in the membrane for some time, and they are known to separate laterally from the (more abundant) glycerolipids, giving rise to highly rigid domains or platforms. The properties of these domains/platforms are rather well understood, but the underlying SM:Cer molecular interactions have not been explored in detail. Infrared (IR) spectroscopy is a powerful analytical technique that provides information on all the chemical groupings in a molecule, and that can be applied to membranes and lipid bilayers in aqueous media. IR spectra can be conveniently retrieved as a function of temperature, thus revealing the thermotropic transitions of SM and its mixtures with Cer. Four regions of the IR spectrum of these sphingolipids have been examined, two of them dominated by the hydrophobic regions in the molecules, namely the C-H stretching vibrations (2800-3000 cm-1), and the CH2 scissoring vibrations (1455-1485 cm-1), and two others arising from chemical groups at the lipid-water interface, the sphingolipid amide I band (1600-1680 cm-1), and the phosphate vibrations in the 1000-1110 cm-1 region. The latter two regions have been rarely studied in the past. The IR data from the hydrophobic components show a gel (or ripple)-fluid transition of SM at 40 °C, that is shifted up to about 70 °C when Cer is added to the bilayers, in agreement with previous studies using a variety of techniques. IR information concerning the polar parts is more interesting. The amide I (carbonyl) band of pure SM exhibits a maximum at 1638 cm-1 at room temperature, and its position is shifted by about 10 cm-1 in the presence of Cer. Cer causes also a change in the overall band shape, but no signs of band splitting are seen, suggesting that SM and Cer carbonyl groups are interacting tightly, presumably through H-bonds. The 1086 cm-1 band, corresponding to PO2- vibrations, appears more stable in SM than in DPPC, and it is further stabilized by Cer, again suggesting an important role of H-bonds in the formation of SM:Cer clusters. Thus, SM and Cer can interact through their polar headgroups, in a way that is not accessible to other lipid classes.

Dataset Information

Synthesis and Liquid Crystalline Properties of Unsymmetrically Substituted Naphthalenediimides with a Polar Headgroup: Effect of Amide Hydrogen Bonding and Alkyl Chain Length.

Publications

Synthesis and Liquid Crystalline Properties of Unsymmetrically Substituted Naphthalenediimides with a Polar Headgroup: Effect of Amide Hydrogen Bonding and Alkyl Chain Length.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets