Novel Fluorescent Dyes by the Extension of the Core of Perylenetetracarboxylic Bisimides

Langhals, Heinz; Kirner, Susanne

doi:10.1002/(sici)1099-0690(200001)2000:2<365::aid-ejoc365>3.3.co;2-i

Cited by 61 publications

(107 citation statements)

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“…The π-electron-rich pyrrole unit and the amino group effectively raise both the HOMO and LUMO level but the former more than the latter, resulting in a smaller energy gap. [15] For the amino-substituted pyrrole-fused perylenebisimide, acylation of the pyrrole nitrogen atom and alkylation of the amino nitrogen increase the dipole moment perpendicular to the long molecular axis and therefore a redshift of the S 0 -S 2 absorption band of MAP-1 (29 nm compared with MAP) is observed, which is larger than that of MAP-2 (5 nm) with a methylated pyrrole nitrogen. The UV/Vis absorption and emission spectra of these compounds are shown in Figure 2 and their photophysical properties are listed in Table 1.…”

Section: Resultsmentioning

confidence: 99%

“…Usually, perylenebisimides are functionalized in the bay region starting from the corresponding brominated or chlorinated derivatives. Palladium-catalyzed ring annulation, [13] photo-triggered intramolecular cyclization, [5b,5c,14] and Diels-Alder reactions [15] are efficient ways of obtaining ring-expanded perylene derivatives. Palladium-catalyzed ring annulation, [13] photo-triggered intramolecular cyclization, [5b,5c,14] and Diels-Alder reactions [15] are efficient ways of obtaining ring-expanded perylene derivatives.…”

Section: Introductionmentioning

confidence: 99%

“…Palladium-catalyzed ring annulation, [13] photo-triggered intramolecular cyclization, [5b,5c,14] and Diels-Alder reactions [15] are efficient ways of obtaining ring-expanded perylene derivatives. [15] However, there are very few examples of amino-substituted perylenes. In addition to the amine-based nucleophilic substitution of brominated PBIs, [16] the nitration of perylenebisimides followed by reduction also yields heterocyclic annulated dyes.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Amino‐Substituted Pyrrole‐Fused Perylenebis(dicarboximide) Derivatives by a One‐Pot Azidation/Reduction/Cyclization

Jiang

et al. 2013

Eur J Org Chem

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Amino‐substituted pyrrole‐fused perylenebis(dicarboximides) have been prepared from tri‐ or tetrabromoperylene prcursors by using the classical azidation conditions for the substitution of aromatic halogen, that is, NaN3, sodium ascorbate, CuI, and N,N‐dimethylethane‐1,2‐diamine in DMSO/H2O. The pyrrole‐fused dyes are highly photochemically and thermally stable, which may be useful for labelling and as building blocks for the synthesis of functional molecular materials.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of Amino‐Substituted Pyrrole‐Fused Perylenebis(dicarboximide) Derivatives by a One‐Pot Azidation/Reduction/Cyclization

Jiang

et al. 2013

Eur J Org Chem

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“…In addition, PBIs have been used as building blocks to construct supramolecular or artificial photosynthetic systems [30,31,32,33]. These organic dyes are advantageous, due to their high molar absorptivities, reversible redox properties and optical stabilities, ease of synthetic modification and excellent thermal stability [34,35,36,37,38,39,40,41,42,43,44,45,46,47,48,49,50,51,52,53,54,55]. The electronic characteristics of PBIs can also be fine-tuned by the substitution of the conjugated aromatic core.…”

Section: Introductionmentioning

confidence: 99%

Green Perylene Bisimide Dyes: Synthesis, Photophysical and Electrochemical Properties

Chang¹,

Tsai²,

Chen³

2014

Materials

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Three asymmetric amino-substituted perylene bisimide dyes with different n-alkyl chain lengths (n = 6, 12, or 18), 1-(N,N-dialkylamino)perylene bisimides (1a-1c), were synthesized under mild condition in high yields and were characterized by 1 H NMR, 13C NMR (nuclear magnetic resonance), HRMS (High Resolution Mass Spectrometer), UV-Vis and fluorescence spectra, as well as cyclic voltammetry (CV). These molecules show intense green color in both solution and solid state and are highly soluble in dichloromethane and even in nonpolar solvents, such as hexane. The shapes of the absorption spectra of 1a-1c in solid state and in solution were found to be virtually the same, indicating that the long alkyl chains could efficiently prevent aggregation. They exhibit a unique charge transfer emission in the near-infrared region, of which the peak wavelengths show strong solvatochromism. The dipole moments of the compounds have been estimated using the Lippert-Mataga equation, and upon excitation, they show larger dipole moment changes than that of 1-aminoperylene bisimide (2). Furthermore, all of the compounds exhibit two quasi-reversible one-electron oxidations and two quasi-reversible one-electron reductions in dichloromethane at modest potentials. Complementary density functional theory (DFT) calculations performed on these dyes are reported in order to rationalize their molecular structures and electronic properties.

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“…PBIs have also been utilized as building blocks to construct supramolecular or artificial photosynthetic systems [30,31,32,33]. These organic molecules are advantageous due to their high molar absorptivities, high photochemical and optical stabilities, reversible redox properties, ease of synthetic modification and excellent thermal stability [34,35,36,37,38,39,40,41,42,43,44,45,46,47,48,49,50,51,52,53,54,55]. The electronic characteristics of PBIs can also be fine-tuned by introducing different substituents at the bay-positions (1,6,7,12-positions) of the conjugated perylene core.…”

Section: Introductionmentioning

confidence: 99%

1,7-Bis-(N,N-dialkylamino)perylene Bisimides: Facile Synthesis and Characterization as Near-Infrared Fluorescent Dyes

Chen

Chang

2014

Materials

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Three symmetric alkylamino-substituted perylene bisimides with different n-alkyl chain lengths (n = 6, 12, or 18), 1,7-bis-(N,N-dialkylamino)perylene bisimides (1a–1c), were synthesized under mild condition and were characterized by 1H NMR, 13C NMR and high resolution mass spectroscopy. Their optical and electrochemical properties were measured using UV-Vis and emission spectroscopic techniques as well as cyclic voltammetry (CV). These compounds show deep green color in both solution and solid state, and are highly soluble in dichloromethane and even in nonpolar solvents such as hexane. The shapes of the absorption spectra of 1a–1c in the solution and solid state were found to be almost the same, indicating that the long alkyl chains could efficiently prevent intermolecular contact and aggregation. They show a unique charge transfer emission in the near-infrared region, of which the peak wavelengths exhibit strong solvatochromism. The dipole moments of the molecules have been estimated using the Lippert–Mataga equation, and upon excitation, they show larger dipole moment changes than that of 1,7-diaminoperylene bisimide (2). Moreover, all the dyes exhibit two irreversible one-electron oxidations and two quasi-reversible one-electron reductions in dichloromethane at modest potentials. Complementary density functional theory calculations performed on these chromophores are reported in order to rationalize their electronic structure and optical properties.

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Novel Fluorescent Dyes by the Extension of the Core of Perylenetetracarboxylic Bisimides

Cited by 61 publications

References 5 publications

Synthesis of Amino‐Substituted Pyrrole‐Fused Perylenebis(dicarboximide) Derivatives by a One‐Pot Azidation/Reduction/Cyclization

Synthesis of Amino‐Substituted Pyrrole‐Fused Perylenebis(dicarboximide) Derivatives by a One‐Pot Azidation/Reduction/Cyclization

Green Perylene Bisimide Dyes: Synthesis, Photophysical and Electrochemical Properties

1,7-Bis-(N,N-dialkylamino)perylene Bisimides: Facile Synthesis and Characterization as Near-Infrared Fluorescent Dyes

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