Absorption spectra of PTCDI: A combined UV–Vis and TD-DFT study

Oltean, Mihai; Calboréan, Adrian; Mile, George; Vidrighin, Mihai; Iosin, Monica; Leopold, Loredana; Maniu, Dana; Leopold, Nicolae; Chiş, Vasile

doi:10.1016/j.saa.2012.07.056

Cited by 54 publications

(58 citation statements)

References 51 publications

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“…Similarly, conversion of PTCA to PDI leads to a further shift of the first and third peaks to longer wavelength but a slight shift of the second peak to shorter wavelength.The first peak of PDI is calculated to occur at 506 nm which is in satisfactory agreement with the experimental value (524 nm) in DMSO. However, we note that solvent effects can be significant for this class of compounds [23]. The peaks for PTCA and PDI arise from a similar set of electronic transitions, as noted for perylene [24].…”

Section: Resultsmentioning

confidence: 86%

Interpreting the near-infrared reflectance of a series of perylene pigments

2013

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This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. and combination modes of fundamental IR vibrations appear to be more important in explaining the observed variations in NIR reflectance/absorbance. Aromatic groups lead to a small number of intense NIR bands, while alkyl groups generally lead to a greater number of less intense NIR bands. However, neighbouring group effects and/or a molecular dipole moment can substantially alter the intensity of these bands.

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Section: Resultsmentioning

confidence: 86%

Interpreting the near-infrared reflectance of a series of perylene pigments

2013

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“…An absorption spectrum similar to the one in the insert of Fig. 1d was observed for other PDIs and was attributed to J-type aggregates [34]. The data suggest that in the case of PDIY the formation of the J-aggregates may be possible due to the network of hydrogen bonds that could involve the hydroxyl group of the Tyr residue and the carboxyl group of the core PDI [33].…”

Section: Resultsmentioning

confidence: 57%

Characterization of novel perylene diimides containing aromatic amino acid side chains

Farooqi

Penick

Burch

et al. 2016

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Perylene diimide derivatives have attracted initial interest as industrial dyes. Recently, much attention has been focused on their strong π–π stacks resulting from the large PDI aromatic core. These PDI stacks have distinct optical properties, and provide informative models that could mimic light-harvesting systems and initial charge transfer typical of photosynthetic systems. The absorption property of PDI derivatives may be tuned from visible to near-infrared region by peripheral substitution. We have studied a new class of PDI derivatives with aryl substituents derived from the side chains of aromatic aminoacids (Tyrosine, Tryptophan and Phenylalanine). We have investigated their absorption and the fluorescence properties in a set of organic solvents and established their different tendencies to aggregate in solution despite their solubility. Most aggregation appears to be unordered. One PDI analogue (the one formed from Tyr) in Methanol, however, appears to form J-type aggregates. Based on our results the compounds appear to be promising for future investigations regarding the interaction of these dyes with biomolecules.

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“…We would like to mention that the use of the common B3LYP functional for excitation energies calculations leads to much larger discrepancies between experiment and theory. Thus, in that case, the largest calculated lambda is 281 nm, that is, a difference of 24 nm from its experimental counterpart, in a range commonly encountered in the literature [91][92][93][94] for this property.…”

Section: Conformation Landscapementioning

confidence: 63%

Conformational landscape and low lying excited states of imatinib

et al. 2015

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The conformational changes of imatinib (IMT) are crucial for understanding the ligand-receptor interaction and its mechanism of action [Agofonov et al. (2014) Nature Struct Mol Biol 21:848-853]. Therefore, here we investigated the free energy conformational landscape of the free IMT base, aiming to describe the three-dimensional structures and energetic stability of its conformers. Forty-five unique conformers, within an energy window of 4.8 kcal mol −1 were identified by a conformational search in gas-phase, at the B3LYP/6-31G(d) theoretical level. Among these, the 20 most stable, as well as 4 conformers resulting from optimization of experimental structures found in the two known polymorphs of IMT and in the cAbl complex were further refined using the 6-31+G(d,p) basis set and the polarizable continuum solvation model. The most stable conformers in gas-phase and water exhibit a V-shaped structure. The major difference between the most stable free conformers and the bioactive conformers consists in the relative orientation of the pyrimidine-pyridine groups responsible for hydrogen bonding interactions in the ATP-binding pocket.The ratio of mole fractions corresponding to the two known (α and β) polymorphic forms of IMT was estimated from the calculated thermochemical data, in quantitative agreement with the existing experimental data related to their solubility. The electronic absorption spectrum of this compound was investigated in water and explained based on the theoretical TD-DFT results, considering the Boltzmann populationaveraged computed data at CAM-B3LYP/6-31+G(d,p) level of theory for the nine most stable conformers.

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Absorption spectra of PTCDI: A combined UV–Vis and TD-DFT study

Cited by 54 publications

References 51 publications

Interpreting the near-infrared reflectance of a series of perylene pigments

Interpreting the near-infrared reflectance of a series of perylene pigments

Characterization of novel perylene diimides containing aromatic amino acid side chains

Conformational landscape and low lying excited states of imatinib

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