The Relation between Packing Effects and Solid State Fluorescence of Dyes

Langhals, Heinz; Demmig, Stefan; Potrawa, Thomas

doi:10.1002/prac.19913330508

Cited by 136 publications

(96 citation statements)

References 20 publications

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“…This value of the extinction coefficient is considerably lower than those reported for simple perylene diimide derivatives. For example, the value for the 524 nm peak of N,N'-dipropyl-3,4,9,10-perylenetetracarboxylic diimide is 78 730 L mol-' cm-' when measured in chlorofom (37 The N,N1-dimethyl and N,Nf-diphenyl diimide derivatives had (normalized spectra).…”

Section: Resultsmentioning

confidence: 99%

Design and synthesis of near-infrared absorbing pigments. II. Structure determination of aceanthrene green and derivatives

Désilets¹,

Kazmaier²,

Burt³

et al. 1995

Can. J. Chem.

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Abstract:The reported structure of aceanthrene green, a pigment prepared by potassium hydroxide fusion of 1.9-anthracenedicarboxylic imide, was found to be incorrect. The structure of the pigment is reassigned to 7,8,15,16-dibenzo[a j]perylenetetracarboxylic diimide on the basis of COSY, NOESY, and inversion-recovery 'H NMR experiments. N-Alkyl-or N-phenyl-l,9-anthracenedicarboxylic imides, aceanthryleno[l,2-blquinoxaline, and a benzimidazole derivative of 1,9-anthracenedicarboxylic anhydride were found to give the same dibenzo[a jlperylene structure when reacted in potassium hydroxide. The electronic spectra of these derivatives is reported and it is shown that, as predicted by Pariser-Parr-Pople calculations, they absorb in the near-infrared. Finally, a mechanistic outline for the fusion is proposed on the basis of AM1 and frontier molecular orbital calculations.Key words: photoconductor, near-infrared, aceanthrene green, alkalifusion, polycyclic aromatic hydrocarbon.RCsumC : On a trouvC que la structure proposCe anterieurement pour l'ackanthrbne vert, un pigment prCparC par fusion de l'imide de l'acide anthracbne-l,9-dicarboxylique avec de l'hydroxyde de potassium, est incorrecte. En se basant sur des expkriences COSY, NOESY et d'inversion-rCcupCration en RMN du 'H on lui a rCattribuC la structure du diimide de l'acide dibenzo[a jlpCrylbne-7,8,15,16-tCtracarboxylique. On a trouvC que par rCaction, par fusion avec de l'hydroxyde de potassium, les N-alkyl-ou N-phCnylimides de l'acide anthrackne-1,9-di-carboxylique, l'acCanthrylCno[l,2-b]quinoxaline et un dCrivC benzimidazole de l'anhydride de l'acide anthracbne-l,9-dicarboxylique conduisent tous B la m&me structure dibenzo[a jlpCrylkne. On rapporte les spectres Clectroniques de ces dCrivCs et il est montrC, tel que prCdit par des calculs de type Pariser-Parr-Pople, qu'ils absorbent dans le proche infrarouge. Enfin, en se basant sur des calculs d'orbitales molCculaires AM1 et frontibres, on propose un aperp du mCcanisme pour la fusion.Mots cles : photoconducteur, proche infrarouge, acCanthrbne vert, fusion alcaline, hydrocarbure polycyclique aromatique.[Traduit par la rCdaction]

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Section: Resultsmentioning

confidence: 99%

Design and synthesis of near-infrared absorbing pigments. II. Structure determination of aceanthrene green and derivatives

Désilets¹,

Kazmaier²,

Burt³

et al. 1995

Can. J. Chem.

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“…A further indication for the intercalation is the fluorescence wavelength of these media, because the dyes are weakly solvatochromic [17]. The fluorescence maximum of 535 nm corresponds well with the maximum in chloroform (534 nm [18]), which is expected to be a medium with similar solvent effects compared to the lipid bilayer of the liposome solution (the fluorescent maximum of the dye is hypsochromically shifted to 523.5 nm in n-heptane as a solvent with low polarity). Even the line form of the emission of the liposomes is the same as for the emission of the dyes in chloroform solution, whereas one observes an aggregation of the dyes [19] with a characteristic broadening of the spectrum in highly polar media like alcohols.…”

Section: Discussionmentioning

confidence: 99%

Labelling of liposomes with intercalating perylene fluorescent dyes

Schott

Cunow

Langhals³

1992

Biochimica et Biophysica Acta (BBA) - Biomembranes

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“…48,64,65 In contrast to primary alkyl groups long-chain secondary alkyl groups give a pronounced increase in solubility when attached to the nitrogen atoms of the perylene dyes. For example, the solubility of 3d is much higher even than the solubility of dye (3c).…”

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confidence: 99%