A two-step synthesis of quaterrylenetetracarboxylic bisimides-novel NIR fluorescent dyes

Langhals, Heinz; Schönmann, Gertrud; Feiler, Leander A.

doi:10.1016/0040-4039(95)01276-n

Cited by 35 publications

(21 citation statements)

References 8 publications

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“…[19,26,27] In addition to the enhanced multistep synthesis involving column chromatography we are looking for a short route usable on a very large scale. Perylenediimides [19] and quaterrylenediimides, [28] the lower and higher homologues of terrylenediimides, can be synthesised by base-promoted homocoupling of naphthalenedicarboximide or perylenedicarboximide, respectively. The obvious synthesis of symmetric ter-rylenediimide 3 in this kind of one-pot base-promoted reaction would depend on heterocoupling of perylenedicarboximide 15 and naphthalenedicarboximide 16.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Modification of Terrylenediimides as High‐Performance Fluorescent Dyes

Nolde

Kohl

et al. 2005

Chemistry A European J

148

119

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Two new synthetic approaches to terrylenediimides, highly photostable fluorescent dyes, are described. For the first time terrylenediimide has been synthesised in a straightforward procedure that makes large quantities available. The second route includes an efficient cross-coupling reaction followed by a cyclodehydrogenation. Monofunctionalisation of the imide structure allows terrylenediimides now to be coupled with a variety of compounds, for example, by Suzuki cross-coupling, which can lead to an array of terrylenediimides with new functional groups such as hydroxy, amino, or carboxy groups needed to link up with other molecules. The functionalisation in the bay region is used to tune the properties of terrylenediimides and extend the range of applications, for example, by introducing water solubility. These tetrasubstituted terrylenediimides offer, depending on the substituents used, exciting features such as good solubility in common organic solvents, water solubility, or NIR absorption.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Modification of Terrylenediimides as High‐Performance Fluorescent Dyes

Nolde

Kohl

et al. 2005

Chemistry A European J

148

119

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“…An alternative approach to achieve near‐red absorber molecules is to extend the π‐electron delocalization of the PDI core structure, through further fused naphthalene units to form higher homologues (e.g., terrylene dyes). [26, 27] The main drawback of this strategy is the reduced water solubility, which is an undesirable effect for PDT applications. Herein, we report a theoretical study of the ground and excited states properties of a series of green water‐soluble PDI chromophores (see Scheme ), bearing at the imide positions polar carboxylic acid derivative group (e.g., CH 2 COOH in 1 and 2 in Scheme ), further polar groups are also present at the bay region (e.g., N ‐(2‐hydroxethyl) in compound 2 ).…”

Section: Introductionmentioning

confidence: 99%

A TDDFT investigation of bay substituted perylenediimides: Absorption and intersystem crossing

2012

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The conformational structure and electronic spectra properties of a series of bay substituted perylenediimides (PDI) derivatives have been investigated by means of density functional theory (DFT) and time‐dependent DFT. The B3LYP and PBE0 hybrid exchange‐correlation functionals were applied in conjunction with the double‐ζ quality SVP basis set. These compounds are interesting for organic materials science and as photosensitizers in cancer phototherapy (PDT), because of their intense absorption in the visible region. Results show that the substitution at the bay position of the PDI parent molecule with N‐alkyl groups shifts the absorption maxima towards the red part of the visible spectrum (around 650–700 nm) as required for the applications in PDT. The main PDT action mechanisms have been investigated by computing of electron affinities, ionization potentials, triplet energies and spin‐orbit matrix elements between singlet and triplet excited states. © 2012 Wiley Periodicals, Inc.

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“…Quaterrylene tetracarboxybisimides [ 39 , 40 ] 1 ( n = 4) being known to be very bathochromically absorbing were rendered soluble [ 41 , 42 ] by the N -(1-hexylheptyl) substituents to obtain 13 and reduced according to 4 . Complete over reduction proceeded to the slightly more bathochromically absorbing bis-anion 15 at 803 nm; see Fig.…”

Section: Resultsmentioning

confidence: 99%

Persistent radical anions in the series of peri-arylenes: broadband light absorption until far in the NIR and purely organic magnetism

Langhals¹,

Ritter-Faizade

Stadler

et al. 2019

Monatsh Chem

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Stable radicals in organic conjugated molecules are of great interest due to their magnetic signals and broad optical absorptions. In this paper, we report on naphthalene, benzoperylene, perylene, terrylene, and quaterrylene carboximides, reduced under controlled conditions, where stable metal-free solid salts of radical anions could be obtained forming darkly colored solutions with line-rich UV/Vis/NIR spectra and exhibiting special magnetic properties. The most bathochromic shift of the absorption maxima extend from 760 until 1700 nm. Persistent paramagnetic properties of the solids were observed and temperature-dependent susceptibilities are measured. Graphical abstract

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A two-step synthesis of quaterrylenetetracarboxylic bisimides-novel NIR fluorescent dyes

Cited by 35 publications

References 8 publications

Synthesis and Modification of Terrylenediimides as High‐Performance Fluorescent Dyes

Synthesis and Modification of Terrylenediimides as High‐Performance Fluorescent Dyes

A TDDFT investigation of bay substituted perylenediimides: Absorption and intersystem crossing

Persistent radical anions in the series of peri-arylenes: broadband light absorption until far in the NIR and purely organic magnetism

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