Luminescence anisotropy and linear dichroism studies of large polycyclic aromatic hydrocarbons based on the perylene chromophore

Marczyk, Jan; Fetzer, John C.; Szubiakowski, Jacek P.; Waluk, Jacek

doi:10.1016/s0022-2313(96)00310-9

Cited by 3 publications

(1 citation statement)

References 8 publications

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“…); therefore, only a few can be used in commercial applications. Polyaromatic hydrocarbons (PAHs) are generally stable under severe conditions and their electronic transitions, for example, absorption, fluorescence, and phosphorescence spectra, show intense response to ultraviolet and/or visible (UV−vis) light owing to their condensed π-conjugations . Therefore, PAHs have been applied to chromogens (dyes, pigments, and fluorescent materials). 2f,g,i,j But the electronic transition properties of such chromophores have been less sufficiently elucidated than those of their parent PAHs and other kinds of chromophores (e.g., azo dye) because the solubility of PAH chromophores is generally too low because of the strong intermolecular interaction between their large planar π-systems.…”

Section: Introductionmentioning

confidence: 99%

Design of Near-Infrared Dyes Based on π-Conjugation System Extension 2. Theoretical Elucidation of Framework Extended Derivatives of Perylene Chromophore

Adachi

Nagao

2001

Chem. Mater.

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To design near-infrared (NIR) absorbing polyaromatic dyes, we have theoretically elucidated the electronic transition properties of the extended π-conjugation derivatives of 3,4,9,10-perylenetetracarboxylic dianhydride diimide (PTCAI). Framework extension along the molecular long axis, that is, to terrylene (TTCAI) and quaterrylene (QTCAI), causes a large bathochromic shift by the narrowing of the HOMO-LUMO gap. Despite the larger π-conjugation, framework expansion along the molecular short axis, that is, to benzo[g,h,i]perylene (bPTCAI) and coronene (CTCAI), causes a hypsochromic shift. Framework extension along the molecular long axis is a beneficial guiding principle of the NIR dye design. To design new polyaromatic chromophores, although the electronic transition properties are roughly determined by the core aromatic structure, we must consider the whole molecule because the modified part plays an important role in controlling the advanced properties.

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Section: Introductionmentioning

confidence: 99%

Design of Near-Infrared Dyes Based on π-Conjugation System Extension 2. Theoretical Elucidation of Framework Extended Derivatives of Perylene Chromophore

Adachi

Nagao

2001

Chem. Mater.

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Fluorescent Probes for the Supramolecular Interactions responsible for Binding of Polycyclic Aromatic Hydrocarbons to Hyperbranched Polyelectrolytes in Aqueous Media

Ihde

Steelman

Bonizzoni

2021

Israel Journal of Chemistry

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Cationic poly(amidoamine) (PAMAM) dendrimers are known as good supramolecular hosts for a variety of smaller water‐soluble guests. We expanded their binding scope to the uptake of very hydrophobic guests such as polycyclic aromatic hydrocarbons (PAH) in neutral aqueous solution. We used anthracene and pyrene as representatives of this family of hydrocarbons, and as capable fluorescent emitters to probe mode and location of interaction for these hydrocarbons with polycationic amine‐terminated PAMAM dendrimers. We used steady‐state and time‐resolved fluorescence emission spectroscopy, as well as fluorescence anisotropy measurements and selective quenching experiments, to establish the mode and location of these binding interactions, demonstrating that, although these probes may look relatively similar, their interaction with PAMAM dendrimers is nevertheless significantly different. The results presented here provide insight into the attractive forces at play in the uptake of featureless hydrophobic PAH guests by hydrophilic PAMAM dendrimer hosts, whose applications span practical challenges including chemical separations, analytical discrimination, solubility and bioavailability enhancement of hydrophobic compounds.

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THE CHEMISTRY AND ANALYSIS OF LARGE PAHs

Fetzer¹

2007

Polycyclic Aromatic Compounds

106

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Luminescence anisotropy and linear dichroism studies of large polycyclic aromatic hydrocarbons based on the perylene chromophore

Cited by 3 publications

References 8 publications

Design of Near-Infrared Dyes Based on π-Conjugation System Extension 2. Theoretical Elucidation of Framework Extended Derivatives of Perylene Chromophore

Design of Near-Infrared Dyes Based on π-Conjugation System Extension 2. Theoretical Elucidation of Framework Extended Derivatives of Perylene Chromophore

Fluorescent Probes for the Supramolecular Interactions responsible for Binding of Polycyclic Aromatic Hydrocarbons to Hyperbranched Polyelectrolytes in Aqueous Media

THE CHEMISTRY AND ANALYSIS OF LARGE PAHs

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