Rotational barriers in perylene fluorescent dyes

Abstract

Attract-Rotational barriers in Il'-substituted perylene dyes have been determined. Phenyl substituents with tert-butyl groups in the o-position give rigid systems, whereas secondary alkyl groups Cause low rotational barriers. In spite of that, fluorescent quantum yields are high in both cases. Conformations in solution are discussed.

The Relation between Packing Effects and Solid State Fluorescence of Dyes

“…The fluorescence is influenced only very little by substituents on the nitrogens. This might be caused by nodes [18] in the wave functions of the 7r orbitals at the nitrogens not only in HOMO and LUMO, but even in the orbital above LUMO and below HOMO. Because of the small influence of the substituents at the nitrogens on optical properties the perylene dyes are an ideal probe for studying crystal packing effects with different N-substituted derivatives.…”

Labelling of liposomes with intercalating perylene fluorescent dyes

“…The high fluorescent potential and exceptional photestability of perylene-3,4:9,10-bis(dicarboximides) in solution have been investigated after the introduction of the solubility increasing dialkylphenylmethyl phenyl groups or long-chain secondary aikyl groups at the nitrogen atoms of the aromatic system [6][7][8][9]. The substituents at the nitrogen atoms of the perylene dr., ?v atires (see For subsequent liposome formation it is crucial that the matrix lipids being the chief constituents of the mixture are well soluble in the used solvent and that a homogeneous lipid film is obtained on concentration of the solution.…”

“…The perylene dyes are prepared from perylene-3,4:9,10-tetracarboxylic bisanhydride, the corresponding amine or amine hydrochloride and imidazole ac-cording to literature procedure [4][5][6][7][8][9]. Special care is taken to prepare highly pure dyes.…”

The Identification of Carbonyl Compounds by Fluorescence: A Novel Carbonyl-Derivatizing Reagent

“…The formation of Schiff bases is expected to be most efficient if the amino group is attached to an imide nitrogen atom of 3, because of the a effect and because of minimal steric hindrance in this position. A further advantage of this position is the fact there are nodes [7] in the HOMO and LUMO of 3. So the UV/visible spectra are only little affected by the structure of the carbonyl compounds to be derivatized.…”